Julia R. Swords Trust, Transferee, Margaret R. Mackell, Dorothy R. Brotherton, and Julia R. Swords, Co-Trustees v. Commissioner , 142 T.C. No. 19 ( 2014 )


Menu:
  •                                  
    142 T.C. No. 19
    UNITED STATES TAX COURT
    JULIA R. SWORDS TRUST, TRANSFEREE, MARGARET R. MACKELL,
    DOROTHY R. BROTHERTON, AND JULIA R. SWORDS, CO-TRUSTEES,
    ET AL.,1 Petitioners v.
    COMMISSIONER OF INTERNAL REVENUE, Respondent
    Docket Nos. 10882-10, 10883-10,            Filed May 29, 2014.
    10884-10, 10885-10.
    R issued notices of transferee liability to Ps to collect D’s
    unpaid Federal income tax pursuant to I.R.C. sec. 6901. R argues that
    the following two-step analysis applies in determining whether Ps are
    liable for D’s unpaid tax: (1) analyze whether the subject transactions
    are recast under Federal law, here primarily the Federal substance
    1
    Cases of the following petitioners are consolidated herewith: David P.
    Reynolds Trust, Transferee, Margaret R. Mackell, Dorothy R. Brotherton, and
    Julia R. Swords, Co-Trustees, docket No. 10883-10; Margaret R. Mackell Trust,
    Transferee, Margaret R. Mackell, Dorothy R. Brotherton, and Julia R. Swords, Co-
    Trustees, docket No. 10884-10; and Dorothy R. Brotherton Trust, Transferee,
    Margaret R. Mackell, Dorothy R. Brotherton, and Julia R. Swords, Co-Trustees,
    docket No. 10885-10.
    -2-
    over form doctrine, and then (2) apply State law to the transactions as
    recast under Federal law.
    Held: I.R.C. sec. 6901 requires that the Court apply State
    (rather than Federal) law to determine whether a transaction is recast
    under a substance over form (or similar) doctrine.
    Held, further, R has failed to establish that an independent
    basis exists under applicable State law or State equity principles for
    holding Ps liable for D’s unpaid tax.
    Timothy L. Jacobs and William Lee S. Rowe, for petitioners.
    Randall L. Eager, Jr., Timothy B. Heavner, Matthew S. Reddington, James
    R. Rich, Kristina L. Rico, and Johnny C. Young, for respondent.
    MARVEL, Judge: These consolidated cases concern separate notices of
    liability that respondent issued to the cotrustees of the Julia R. Swords Trust
    (Swords Trust), the David P. Reynolds Trust (Reynolds Trust), the Margaret R.
    Mackell Trust (Mackell Trust), and the Dorothy R. Brotherton Trust (Brotherton
    Trust) (collectively, petitioner trusts).2 Respondent determined in the notices that
    petitioner trusts are liable as transferees for Davreyn Corp.’s (Davreyn) Federal
    2
    The cotrustees of each of these trusts are Margaret R. Mackell, Dorothy R.
    Brotherton, and Julia R. Swords.
    -3-
    income tax deficiency of $4,602,986,3 additions to tax under section 6651(a)(1)
    and (2)4 of $1,160,137 and $1,982, respectively, an accuracy-related penalty under
    section 6662 of $920,597, fees of $50, and related interest for Davreyn’s taxable
    year ended (TYE) February 15, 2001. The amount of each petitioner trust’s
    transferee liability as calculated by respondent is as follows: Swords Trust--
    $3,833,988, Reynolds Trust--$2,710,241, Mackell Trust--$3,833,988, and
    Brotherton Trust--$3,833,988. These calculated liabilities stem primarily from
    respondent’s determination recharacterizing petitioner trusts’ February 15, 2001,
    sales5 of their Davreyn stock as a sale of assets by Davreyn followed by Davreyn’s
    distribution of its assets to petitioner trusts in liquidation.
    The sole issue for decision is whether petitioner trusts are liable as
    transferees under section 6901 for Davreyn’s unpaid Federal income tax liability
    3
    Some monetary amounts have been rounded to the nearest dollar.
    4
    Unless otherwise indicated, section references are to the applicable
    versions of the Internal Revenue Code, as amended, and Rule references are to the
    Tax Court Rules of Practice and Procedure.
    5
    Our use in the findings of fact of “sale”, “purchase”, and similar words
    generally is for convenience and is not intended to, and does not, constitute a
    finding that the referenced transactions were valid transactions recognized for
    Federal income tax purposes.
    -4-
    for Davreyn’s TYE February 15, 2001. We hold that petitioner trusts are not
    liable as transferees under section 6901.
    FINDINGS OF FACT
    Some facts have been stipulated and are so found. The stipulations of fact
    and the facts drawn from stipulated exhibits are incorporated herein by this
    reference. When the petitions were filed, each petitioner trust had a mailing
    address in Virginia. Also at that time, Ms. Mackell and Ms. Brotherton resided in
    Virginia, and Ms. Swords resided in Kentucky.
    I.    The Reynolds Family and Petitioner Trusts
    In 1919 Richard S. Reynolds, Sr., founded the Reynolds Metal Co.
    (Reynolds Metal). Reynolds Metal produced the popular aluminum foil brand,
    Reynolds Wrap. Headquartered in Richmond, Virginia, Reynolds Metal was, at
    one time, the third largest aluminum company in the world.
    David Parham Reynolds (Mr. Reynolds), who died on August 29, 2011, was
    the son of Richard S. Reynolds, Sr., and the sole beneficiary of the Reynolds
    Trust. The Reynolds Trust was established by an instrument of indenture dated
    May 14, 1932.
    Mr. Reynolds’ only children are his daughters: Ms. Swords, Ms. Mackell,
    and Ms. Brotherton. Ms. Swords and her descendants are the sole beneficiaries of
    -5-
    the Swords Trust. Ms. Mackell and her descendants are the sole beneficiaries of
    the Mackell Trust. Ms. Brotherton and her descendants are the sole beneficiaries
    of the Brotherton Trust. The Swords Trust, the Mackell Trust, and the Brotherton
    Trust were established by separate instruments of indenture dated February 22,
    1957.
    When Mr. Reynolds became ill in the late 1990s, Ms. Swords, Ms. Mackell,
    and Ms. Brotherton became primarily responsible for managing petitioner trusts.
    They served as cotrustees for petitioner trusts at all relevant times. Robert H.
    Griffin, a certified public accountant (C.P.A.) and a partner at the Virginia
    accounting firm of Mitchell Wiggins & Co., LLP (Mitchell Wiggins), has
    provided accounting and tax services to petitioner trusts for decades.
    II.     Davreyn
    In 1961 Davreyn was established and began business as a Virginia
    corporation. At all relevant times Davreyn was a personal holding company
    (PHC). Each petitioner trust received a substantial number of Davreyn shares at
    the time of Davreyn’s formation.
    Before June 2000 Davreyn held a substantial number of shares in Reynolds
    Metal. In June 2000 Reynolds Metal merged with Alcoa, Inc. (Alcoa), another
    -6-
    American aluminum company, and Davreyn’s existing Reynolds Metal shares
    were converted into Alcoa shares.
    As of February 1, 2001, Davreyn had assets as follows: (1) 409,830 shares
    of Alcoa stock and (2) an investment in the Goldman Sachs 1999 Exchange Place
    Fund (Goldman Sachs fund). The value of the Alcoa stock held by Davreyn
    exceeded $14 million as of February 2001.
    As of February 14, 2001, the Swords Trust, the Mackell Trust, and the
    Brotherton Trust owned all of Davreyn’s common stock. Each trust owned 1,656
    of the 4,968 issued and outstanding shares of Davreyn’s common stock. The
    Reynolds Trust owned all of the 35,428 issued and outstanding shares of
    Davreyn’s preferred stock.
    Also as of February 14, 2001, Davreyn had officers and directors as follows:
    (1) Ms. Mackell, who served as president, treasurer, and director, (2) Ms. Swords,
    who served as vice president and director, (3) Ms. Brotherton, who served as vice
    president and director, and (4) Mr. Griffin, who served as secretary and director.
    Mr. Griffin also served as an accountant and adviser to Davreyn, and he prepared
    its Federal income tax returns for its taxable years before the year in issue. Before
    the transactions at issue, neither Ms. Swords, Ms. Mackell, nor Ms. Brotherton
    -7-
    made any change to Davreyn’s operation, except for diversifying Davreyn’s
    holdings by investing in the Goldman Sachs fund.
    III.   Petitioner Trusts’ Sales of Davreyn Stock
    A.    Initial Meetings and Negotiations
    In the late 1990s BDO Seidman, an accounting firm, advised its local
    offices about an opportunity for PHC shareholders to sell their appreciated PHC
    stock to a financial buyer in a tax efficient manner. Jon Glazman, a C.P.A. with
    BDO Seidman, contacted several attorneys, including Tom Word, an attorney at
    McGuireWoods LLP (McGuireWoods), to inform them of this opportunity. Mr.
    Word relayed this opportunity to other McGuireWoods attorneys, including
    Thomas Rohman, a tax partner. Mr. Rohman later contacted Mr. Glazman about a
    potential sale of PHC stock by clients of Mr. Rohman. Mr. Glazman put Mr.
    Rohman in touch with Maurice Gottlieb, another C.P.A. at BDO Seidman who
    specialized in PHC stock sale transactions. Eventually, Mr. Rohman and Mr.
    Glazman began working together to sell PHC stock to financial buyers. As of the
    beginning of February 2000 Mr. Gottlieb had structured several transactions
    similar to the one at issue with the assistance of Mr. Rohman.
    Mr. Rohman at some point contacted Mr. Griffin and advised him of the
    opportunity for shareholders to sell their PHC stock to a financial buyer.
    -8-
    Although neither Mr. Griffin nor petitioner trusts were marketing or seeking to
    market Davreyn, Mr. Griffin recognized that Davreyn was a candidate for this
    opportunity because Davreyn was a PHC that held highly appreciated stock. On
    or before February 10, 2000, Mr. Griffin mentioned to Mr. Rohman that Davreyn
    was such a possible candidate, and Mr. Rohman relayed that information to Mr.
    Gottlieb.
    On February 10, 2000, at Mr. Gottlieb’s request, Mr. Rohman sent to Mr.
    Gottlieb and Mr. Glazman an email providing more detailed information about a
    potential sale of Davreyn’s stock, including information about Davreyn’s tax basis
    in its assets. In the email Mr. Rohman indicated that Davreyn held two assets, the
    total market value of which was $15,526,639. These assets were: (1) 193,317
    shares of Reynolds Metal common stock, with a market value of $14,498,775, and
    (2) the Goldman Sachs fund shares, with a market value of $1,027,864.
    On March 7, 2000, Mr. Rohman and Mr. Griffin again discussed a potential
    sale of Davreyn’s stock.6 Nine days later, a meeting was held between Ms.
    6
    Mr. Griffin testified that this discussion was the first time he knew that
    there was a buyer interested in purchasing Davreyn stock. However, Mr. Rohman
    sent the February 10, 2000, email to Mr. Gottlieb and Mr. Glazman containing
    detailed information about Davreyn. We therefore reject the referenced testimony
    and find that Mr. Rohman and Mr. Griffin discussed the sale of Davreyn stock on
    or before February 10, 2000.
    -9-
    Mackell, Ms. Brotherton, Mr. Rohman, Mr. Griffin, and Lizzie Amos, a manager
    at Mitchell Wiggins. At the meeting Mr. Griffin and Ms. Amos advised Ms.
    Mackell and Ms. Brotherton that petitioner trusts had five options with respect to
    Davreyn: (1) continue Davreyn, (2) liquidate Davreyn, (3) sell Davreyn’s stock
    for 90% of the fair market value (FMV) of its assets, (4) sell Davreyn’s stock for
    the sum of 90% of the FMV of the Reynolds Metal stock plus 25% of the FMV of
    the Goldman Sachs fund shares, or (5) sell Davreyn’s stock for 90% of the FMV
    of the Reynolds Metal stock and distribute the Goldman Sachs fund shares to a
    limited liability company (LLC). Mr. Griffin advised Ms. Mackell and Ms.
    Brotherton regarding the potential sale price, as well as the mechanics and tax
    consequences of a potential sale of Davreyn’s stock.
    Because of the merger between Reynolds Metal and Alcoa, any plans
    regarding the sale of Davreyn’s stock were put on hold. After the merger, in
    September 2000, Mr. Rohman again met with Mr. Griffin, Ms. Mackell, and Ms.
    Brotherton to discuss the potential sale of Davreyn’s stock to a financial buyer. At
    the meeting Mr. Rohman did not discuss the buyer’s plans with respect to either
    Davreyn or Davreyn’s assets.
    Following the meeting, on September 8, 2000, Mr. Rohman sent to Ms.
    Swords, Ms. Mackell, and Ms. Brotherton a memorandum reiterating his
    - 10 -
    presentation and outlining the proposed sale transaction. In the memorandum Mr.
    Rohman advised that, because of the financial buyer’s “peculiar” tax situation, a
    sale of Davreyn’s stock to the financial buyer would be an attractive option for
    petitioner trusts. Mr. Rohman also stated that the financial buyer would not be
    interested in purchasing Davreyn if it held any assets other than the Alcoa stock.7
    To account for the existence of the other asset, namely, the Goldman Sachs fund
    shares, Mr. Rohman proposed that the transaction proceed as follows: (1)
    Davreyn organizes an LLC, (2) Davreyn transfers the Goldman Sachs fund shares
    to the LLC, (3) Davreyn distributes to petitioner trusts the ownership interests in
    the LLC in exchange for some of their Davreyn shares, and (4) petitioner trusts
    sell their Davreyn stock to the financial buyer for cash. Mr. Rohman advised that
    the purchase price for the Davreyn stock would equal: (1) 90% of the FMV of the
    Alcoa stock, (2) 100% of all the accrued dividends on the Alcoa stock, and (3)
    100% of Davreyn’s cash on hand at closing, “less the amount of the estimated
    corporate income tax incurred by it on the distribution” of the Goldman Sachs
    fund shares to the LLC.
    7
    Mr. Rohman calculated Davreyn’s assets as follows: (1) Alcoa stock, with
    an estimated tax basis of $1 million and an estimated value of $13,857,000 and (2)
    Goldman Sachs fund shares, with an estimated tax basis of $167,000 and an
    estimated value of $860,000.
    - 11 -
    With respect to the tax consequences, Mr. Rohman advised that petitioner
    trusts would recognize long-term capital gain in amounts equal to the difference
    between the total stock sale price and petitioner trusts’ tax bases in their Davreyn
    stock. He further advised that after the transaction, petitioner trusts would own
    100% of the LLC and that the LLC would have a tax basis in the Goldman Sachs
    fund shares equal to their FMV. Mr. Rohman noted that Davreyn would recognize
    taxable gain equal to the difference between its tax basis and the FMV of the
    Goldman Sachs fund shares and that “[t]he burden of this corporate income tax
    liability would effectively fall on the shareholders because the Buyer would
    reduce the Purchase Price by the amount of this corporate income tax liability.”
    Mr. Rohman concluded that petitioner trusts would recognize long-term capital
    gain of $13,031,000 and pay tax of $3,356,000 with respect to the proposed stock
    sale.8
    Although Ms. Swords, Ms. Mackell, and Ms. Brotherton had not previously
    considered selling petitioner trusts’ shares in Davreyn, arranging a sale of
    Davreyn’s assets, or liquidating Davreyn, they agreed on the advice of Mr. Griffin
    and Mr. Rohman to sell petitioner trusts’ Davreyn stock to the financial buyer.
    8
    Mr. Rohman calculated petitioner trusts’ tax liabilities assuming a 20%
    Federal income tax rate and a 5.75% State income tax rate.
    - 12 -
    Neither Mr. Griffin, Ms. Swords, Ms. Mackell, nor Ms. Brotherton were aware of
    the buyer’s identity or the buyer’s plan with respect to Davreyn or the Alcoa stock
    Davreyn owned. The buyer was not acting as the agent of petitioner trusts, and
    Ms. Swords, Ms. Mackell, and Ms. Brotherton were not aware of any plan by the
    financial buyer to cause Davreyn or any other taxpayer to illegitimately avoid the
    payment of tax. Mr. Griffin subsequently contacted Mr. Rohman to advise him
    that petitioner trusts wanted to sell their Davreyn stock to the financial buyer.
    On September 13, 2000, Mr. Rohman sent an email to the chief financial
    officer (CFO) of Integrated Capital Associates (ICA),9 Howard B. Teig,10
    regarding the proposed stock sale transaction. In the email Mr. Rohman described
    Davreyn and indicated that Davreyn would transfer the Goldman Sachs fund
    shares to an LLC before the proposed stock sale. After exchanging a series of
    9
    ICA was an investment banking firm incorporated under Delaware law and
    based in New York City and San Francisco. ICA had a number of affiliates,
    including Integrated Acquisition Group, LLC (IAG), and ICA Fund Manager, Inc.
    (ICA Fund Manager). In addition to his role as CFO of ICA Fund Manager, Mr.
    Teig served as CFO of IAG and ICA Fund Manager.
    10
    Mr. Teig, a C.P.A., performed all of ICA’s accounting work, including the
    preparation of its tax returns. With respect to financial transactions between ICA
    and a third party, Mr. Teig performed due diligence and worked with the third
    parties and outside counsel to finalize the transactions.
    - 13 -
    emails, on September 15, 2000, Mr. Teig sent to Mr. Rohman an email with an
    attached draft letter of intent.
    B.     Formation of Davreyn LLC
    On September 15, 2000, Mr. Rohman caused Davreyn LLC to be formed.
    At formation Davreyn was the sole member of Davreyn LLC. Ms. Mackell and
    Ms. Brotherton were the initial managers of Davreyn LLC.
    C.     Letter of Intent and Stock Purchase Agreement
    On December 14, 2000, Mr. Rohman emailed Mr. Teig to inform him that
    the officers and directors of Davreyn had agreed to the proposed stock sale. After
    exchanging emails Mr. Rohman sent to Mr. Teig an email with an attached draft
    letter of intent.
    On January 19, 2001, ICA sent a letter of intent to Davreyn. The letter of
    intent proposed a purchase price equal to: (1) 90% of the FMV of Davreyn’s
    marketable securities plus (2) 100% of Davreyn’s cash and accrued dividend and
    interest income. The letter provided that petitioner trusts would permit ICA to
    conduct a full due diligence review of Davreyn before closing. The letter also
    provided that the buyer would obtain sufficient acquisition financing. Mr. Teig
    signed the letter of intent as CFO of ICA. Ms. Swords, Ms. Mackell, and Ms.
    - 14 -
    Brotherton executed the letter of intent on behalf of petitioner trusts and returned
    the executed letter of intent to ICA on January 26, 2001.
    On January 22, 2001, Mr. Rohman sent to Mr. Teig an initial draft of the
    Stock Purchase and Redemption Agreement (stock purchase agreement). With
    respect to the tax consequences of the transaction, the stock purchase agreement
    provided that, among other things: (1) the purchase price payable on the closing
    date would be reduced by an amount equal to the net interim tax liability,11 (2) the
    buyer would prepare and file any returns on behalf of Davreyn and pay the related
    tax for any taxable periods beginning before the closing date and ending after the
    closing date, (3) the buyer would not cause Davreyn to become a member of a
    consolidated group for tax purposes after the closing,12 and (4) the redemption
    transaction would qualify as a redemption treated as an exchange pursuant to
    11
    The stock purchase agreement provided that the net interim tax liability
    would be equal to the difference between the quarterly tax estimate and the interim
    tax liability. The quarterly tax estimate would be equal to Davreyn’s estimated tax
    payments for the period beginning January 1, 2001, and ended April 15, 2001.
    The interim tax liability would be equal to Davreyn’s estimated Federal and State
    tax liability for the period beginning January 1, 2001, and ended on the closing
    date. In the closing statement Mitchell Wiggens calculated the interim tax liability
    as $49,800.
    12
    The stock purchase agreement also provided that after the closing the
    buyer would file articles of amendment with the Virginia State Corporation
    Commission to change Davreyn’s name.
    - 15 -
    section 302(b)(3). While the stock purchase agreement indicated that the buyer
    was a statutory trust, the stock purchase agreement did not identify the buyer by
    name.
    On February 6, 2001, Dan L. Rosenbaum13 emailed Mr. Rohman and Mr.
    Teig an edited copy of the stock purchase agreement. In the edited stock purchase
    agreement, Mr. Rosenbaum changed the purchaser’s name to Alrey Statutory Trust
    (Alrey Trust). Alrey Trust14 was a Connecticut statutory trust established by First
    Union and Alrey LLC.15
    13
    Mr. Rosenbaum was an attorney at the law firm of Sonnenschein, Nath &
    Rosenthal LLP (Sonnenschein).
    14
    On February 7, 2001, Alrey LLC and First Union National Bank (First
    Union) entered into a trust agreement to establish Alrey Trust. Mr. Teig, acting as
    CFO of ICA Fund Manager (at the time, the manager of Alrey LLC), signed the
    trust agreement on behalf of Alrey LLC, the trustor. W. Jeffrey Kramer, acting as
    vice president of First Union, signed the trust agreement on behalf of First Union,
    the trustee. Alrey Trust was terminated on June 16, 2003.
    15
    Alrey LLC, a Delaware limited liability company, was formed on February
    6, 2001. Mr. Rosenbaum acted as incorporator for Alrey LLC. At the time of
    formation IAG was the sole member of Alrey LLC. ICA Fund Manager was the
    initial manager of Alrey LLC. At all relevant times Alrey LLC was treated as a
    disregarded entity for Federal income tax purposes pursuant to sec. 301.7701-
    2(c)(2)(i), Proced. & Admin. Regs.
    - 16 -
    D.    Davreyn’s Closing Preparations
    Mr. Teig requested that Mr. Rohman instruct Davreyn to: (1) open an
    account at DB Alex. Brown, LLC, a subsidiary of Deutsche Bank AG
    (collectively, Deutsche Bank) and (2) transfer its Alcoa stock to Davreyn’s newly
    opened Deutsche Bank account. Accordingly, on February 9, 2001, Ms. Mackell
    and Ms. Brotherton executed an account agreement to open a brokerage account
    with Deutsche Bank on behalf of Davreyn. On February 13, 2001, Davreyn
    transferred its Alcoa stock to its Deutsche Bank account.
    E.    IAG’s Transfer of Alrey Trust
    On February 13, 2001, in exchange for $525,000, IAG assigned to Alrey
    Acquisition Corp. (Alrey Acquisition)16 its 100% membership interest in Alrey
    LLC, the trustor of Alrey Trust. Following the transfer Mr. Austin was appointed
    as the manager of Alrey LLC. Accordingly, as of February 13, 2001, Alrey LLC
    was owned outright by Alrey Acquisition, which had only one shareholder, Sunny
    Capital. Furthermore, as of February 13, 2001, Mr. Austin was the manager of
    16
    Alrey Acquisition, a Delaware corporation, was formed on February 6,
    2001. Mr. Rosenbaum acted as incorporator for Alrey Acquisition. On February
    6, 2001, Mr. Rosenbaum, acting on behalf of Alrey Acquisition, adopted a
    resolution electing Larry J. Austin as the sole director of Alrey Acquisition.
    Sunny Capital Assets 1999 Trust (Sunny Capital) was the sole shareholder of
    Alrey Acquisition. Mr. Austin was the trustee of Sunny Capital.
    - 17 -
    Alrey LLC and the sole director, president, secretary, and treasurer of Alrey
    Acquisition.
    F.       Alrey Trust’s Financing
    Integrated Holdings Ltd. (Integrated Holdings), a company in the Cayman
    Islands,17 provided financing, via a loan and a promissory note, for Alrey Trust’s
    acquisition of Davreyn’s stock. On February 14, 2001, $16 million was deposited
    into Alrey Trust’s account at First Union, presumably by Integrated Holdings.
    G.       The Redemption Transaction
    On February 15, 2001, Davreyn transferred the Goldman Sachs fund shares
    to Davreyn LLC in exchange for a 100% membership interest in Davreyn LLC.
    Davreyn then redeemed 1 share of its issued and outstanding common stock from
    each of the Swords Trust, the Mackell Trust, and the Brotherton Trust in exchange
    for the distribution of one-third of its membership interest in Davreyn LLC to each
    of those trusts. Following the redemption transaction the Swords Trust, the
    Mackell Trust, and the Brotherton Trust each owned 1,655 shares of Davreyn
    common stock and a one-third membership interest in Davreyn LLC.
    17
    ICA and First Union planned to use Integrated Holdings as a financier for
    the Davreyn stock sale transaction as early as February 7, 2001. Mr. Teig testified
    that Integrated Holdings was a third party unrelated to ICA. However, he later
    testified that ICA often established entities that began with the word “integrated”
    and admitted that it was possible that ICA established Integrated Holdings.
    - 18 -
    H.     The Stock Sale Transaction
    Davreyn, petitioner trusts, and Alrey Trust entered into the stock purchase
    agreement on February 15, 2001. Ms. Mackell executed the stock purchase
    agreement on behalf of Davreyn, Ms. Swords, Ms. Mackell, and Ms. Brotherton
    executed the stock purchase agreement on behalf of petitioner trusts, and Mr.
    Kramer executed the stock purchase agreement on behalf of Alrey Trust.
    Pursuant to the stock purchase agreement, on February 15, 2001, the Swords
    Trust, the Mackell Trust, and the Brotherton Trust each sold 1,655 shares of
    Davreyn common stock and the Reynolds Trust sold all of its shares of Davreyn
    preferred stock to Alrey Trust. In exchange Alrey Trust transferred $13,102,055
    in cash to an escrow account held by McGuireWoods.18 On that same date the
    cash proceeds were wired from the McGuireWoods escrow account to petitioner
    trusts’ accounts at Merrill Lynch as follows: Reynolds Trust--$2,673,431, Swords
    Trust--$3,416,891, Mackell Trust--$3,416,891, Brotherton Trust--$3,416,891. A
    portion of the cash proceeds was used to pay petitioner trusts’ representatives;
    18
    According to the closing statement the $13,102,055 equaled (1) 90% of
    the $14,544,867 FMV of Davreyn’s Alcoa stock as determined on the basis of
    Alcoa’s closing price on February 14, 2001, plus (2) $61,475 of accrued
    dividends, less (3) a $49,800 interim tax liability as computed by Mitchell
    Wiggins.
    - 19 -
    McGuireWoods and Mitchell Wiggins received payments of $139,500 and
    $38,450, respectively.
    Mr. Griffin and Ms. Swords, Ms. Mackell, and Ms. Brotherton then
    resigned from their positions as the officers and directors of Davreyn, effective
    February 15, 2001. By letter dated February 15, 2001, Ms. Mackell released her
    authority over Davreyn’s Deutsche Bank account.
    IV.   Alrey Trust’s Pre- and Post-Closing Transactions
    A.     Background
    On February 14, 2001, in anticipation of the closing of the sale with respect
    to Alrey Trust’s purchase of Davreyn’s stock, Alrey Trust entered into a stock
    purchase agreement with Deutsche Bank for the sale of Davreyn’s Alcoa stock.
    On the same day, Mr. Kramer accepted the Deutsche Bank offer on behalf of Alrey
    Trust. The stock purchase agreement between Deutsche Bank and Alrey Trust
    provided that the sale price would be determined on the basis of Alcoa’s closing
    price on February 14, 2001. Alcoa stock closed at $35.49 per share on February
    14, 2001.
    B.     Davreyn’s Liquidation and Other Post-Closing Transactions
    By documents dated February 15, 2001, Mr. Kramer, acting on behalf of
    Alrey Trust, and Mr. Austin, acting as director of Davreyn, resolved that Davreyn
    - 20 -
    be completely liquidated in accordance with section 331. In an attached plan of
    liquidation Mr. Austin provided that Davreyn would distribute all of its assets to
    Alrey Trust in redemption and cancellation of all of the outstanding Davreyn
    stock. Further, on February 15, 2001, Mr. Austin authorized dissolution of
    Davreyn and caused to be filed with the Virginia State Corporation Commission
    articles terminating Davreyn’s corporate existence.
    Davreyn was liquidated on February 15, 2001, and its assets were
    distributed to Alrey Trust. Mr. Austin directed Deutsche Bank to transfer the
    Alcoa stock in Davreyn’s Deutsche Bank account to Alrey Trust’s account at
    Deutsche Bank, and Deutsche Bank did so. In addition, Sunny Capital assigned to
    Alrey Acquisition its shares of common stock of BMY Acquisition Corp.
    (BMY).19 Davreyn was terminated and dissolved effective February 27, 2001.
    Pursuant to their earlier agreement, Alrey Trust ultimately transferred the
    Alcoa stock to Deutsche Bank in exchange for $14,446,020 in net proceeds.20 On
    February 20, 2001, Deutsche Bank deposited $14,446,010 of the net sales
    19
    Mr. Austin signed the assignment of shares document in his capacity as
    trustee of Sunny Capital and as chairman of Alrey Acquisition.
    20
    The gross proceeds from the sale were $14,544,867. Deutsche Bank
    calculated the net proceeds by eliminating from the gross proceeds the following
    amounts: (1) commissions of $98,359, (2) a Securities and Exchange Commission
    fee of $485, and (3) a handling fee of $3.
    - 21 -
    proceeds into Alrey Trust’s account.21 Also on that day, Alrey Trust, at the
    direction of Mr. Austin, transferred $16,139,452 from its account at First Union to
    an account at ABN Amro Bank N.V., held under the name MeesPierson
    (Bahamas) Ltd. Alrey Trust designated this amount as a “loan repayment”. After
    the transfer Alrey Trust’s First Union bank account had a balance of $679,504.
    Between April 2001 and June 2003 a number of payments were made from
    Alrey Trust’s First Union bank account to various entities and individuals,
    including BDO Seidman, WC Investments, Inc.,22 Emil Pesiri,23 Bingham Dana
    LLP, Sonnenschein, Cooper, Brown & Behrle, First Union, Vandalia, LLC, ICA,
    and Starwalker Group, LLC (Starwalker).24 On June 19, 2003, Alrey Trust’s First
    Union bank account was closed.
    21
    The $14,446,010 figure is equal to the net proceeds from Alrey Trust’s
    sale of the Alcoa stock, minus a wire transfer fee of $10.
    22
    WC Investments, Inc., was owned by George Theofel. Mr. Theofel was a
    former employee and/or representative of ICA.
    23
    Mr. Pesiri was a former employee and/or representative of ICA.
    24
    Starwalker was an entity established and owned by Mr. Austin. Mr.
    Austin served as president of Starwalker during the relevant period.
    - 22 -
    V.    Tax Reporting
    A.    Petitioner Trusts
    Each petitioner trust timely filed a Form 1041, U.S. Income Tax Return for
    Estates and Trusts, for 2001. Mr. Griffin prepared petitioner trusts’ Forms 1041.
    On a Schedule D, Capital Gains and Losses, attached to its Form 1041 the
    Reynolds Trust reported a $2,664,196 gain from the stock sale. On Schedules D
    attached to their Forms 1041, the Swords Trust, the Mackell Trust, and the
    Brotherton Trust each reported a $3,628,247 gain from the sale of the Davreyn
    common stock and from the redemption of Davreyn stock relating to the Goldman
    Sacks fund shares. For 2001 petitioner trusts paid Federal income tax as follows:
    Reynolds Trust--$532,722, Swords Trust--$726,356, Mackell Trust--$726,555,
    and Brotherton Trust--$726,544.
    B.    Davreyn
    On September 30, 2002, Davreyn mailed to respondent a Form 1120, U.S.
    Corporation Income Tax Return, for the period January 1 to February 15, 2001.25
    Mr. Teig prepared the Form 1120 and Mr. Austin executed it.
    25
    Before the transactions at issue Davreyn used a TYE December 31 for
    financial and tax accounting purposes.
    - 23 -
    On the Form 1120 Davreyn reported total income of $558,440, including
    dividends of $61,475, interest of $24, and capital gains of $496,941. On an
    attached Schedule D Davreyn reported a short-term capital gain of $496,941
    attributable to the sale of the “investment in Davreyn LLC”. Davreyn reported a
    basis in the Davreyn LLC investment of $1,076,530 and a sale price of
    $1,573,471, and a Federal income tax liability of $37,560, on its Form 1120.
    C.     Alrey Trust
    Alrey Trust filed a Form 1041 for the taxable year beginning February 7,
    2001, and ended January 31, 2002. Alrey Trust attached to its Form 1041 a
    grantor letter identifying Alrey Acquisition as its grantor. The grantor letter
    reported a long-term capital gain of $13,424,010, arising from the sale of 409,830
    shares of Alcoa stock. The grantor letter stated that: (1) Alrey Trust acquired the
    Alcoa stock on December 14, 1961, (2) Alrey Trust had a basis in the Alcoa stock
    of $1,022,000, (3) Alrey Trust sold the Alcoa stock on February 15, 2001, for a
    gross sale price of $14,446,010, and (4) Alrey Trust’s income, deductions, and
    credits would be reported on Alrey Acquisition’s Federal income tax return.
    D.     Alrey Acquisition
    Alrey Acquisition filed a Form 1120 for the taxable year beginning
    February 6, 2001, and ended January 31, 2002. On its Form 1120 Alrey
    - 24 -
    Acquisition reported interest income of $10,506 and a net loss of $615,543, for a
    total taxable loss of $605,037 and total tax of zero. On an attached Schedule D
    Alrey Acquisition reported long-term capital gain from its passthrough entities of
    $13,424,010 and a short-term capital loss of $13,727,689, resulting from its sale of
    the BMY stock.26
    26
    With respect to the BMY stock, Alrey Acquisition reported a basis of
    $13,744,939 and a sale price of $17,250. Alrey Acquisition reported that it
    acquired the BMY stock on February 15, 2001, and that it sold the BMY stock on
    December 17, 2001.
    Respondent has alleged that Alrey Acquisition’s sale of the Alcoa stock and
    the BMY stock were parts of a Son-of-BOSS transaction. A Son-of-BOSS
    transaction can be summarized as follows:
    [A] variation of a slightly older alleged tax shelter known as BOSS,
    an acronym for “bond and options sales strategy.” There are a
    number of different types of Son-of-BOSS transactions, but what they
    all have in common is the transfer of assets encumbered by significant
    liabilities to a partnership, with the goal of increasing basis in that
    partnership. The liabilities are usually obligations to buy securities,
    and typically are not completely fixed at the time of transfer. This
    may let the partnership treat the liabilities as uncertain, which may let
    the partnership ignore them in computing basis. If so, the result is
    that the partners will have a basis in the partnership so great as to
    provide for large--but not out-of-pocket--losses on their individual
    tax returns.
    Kligfeld Holdings v. Commissioner, 
    128 T.C. 192
    , 194 (2007).
    - 25 -
    VI.   Audit of Alrey Acquisition and Davreyn
    In June 2005 the Internal Revenue Service (IRS) began an examination of
    Alrey Acquisition. As a result of the examination respondent issued to Alrey
    Acquisition a notice of deficiency disallowing its claimed losses from the BMY
    stock sale. By letters dated August 8, 2006, respondent informed petitioner trusts
    that respondent had examined their potential transferee liability with respect to
    Alrey Acquisition and determined that a transferee examination would not
    proceed.
    In June 2006 the IRS began an examination of Davreyn. After examining
    Davreyn’s Form 1120 respondent determined that the purported sale of Davreyn’s
    stock to Alrey Trust should be recharacterized as a sale of assets by Davreyn
    followed by a distribution of Davreyn’s assets to its shareholders in liquidation.
    On the basis of this determination respondent increased Davreyn’s long-term
    capital gain by $13,444,080 and determined a deficiency in its Federal income tax
    of $4,602,986.
    VII. Notice of Deficiency, Assessment, and Collection
    Respondent mailed to Davreyn a notice of deficiency dated September 23,
    2008, for its TYE February 15, 2001. In the notice of deficiency respondent
    determined a deficiency in Davreyn’s Federal income tax of $4,602,986, an
    - 26 -
    addition to tax under section 6651(a)(1) of $1,160,137, an accuracy-related
    penalty under section 6662 of $920,597, and accrued interest of $3,807,128.
    Davreyn did not file a petition in this Court contesting respondent’s
    determinations. Accordingly, respondent treated the notice of deficiency as
    defaulted and, on January 14, 2009, assessed Davreyn’s tax deficiency of
    $4,602,986, as well as additions to tax under section 6651(a)(1) and (2) of
    $1,160,137 and $1,982, respectively, an accuracy-related penalty under section
    6662 of $920,597, and related interest.
    VIII. Notices of Liability
    On February 25, 2010, respondent sent notices of liability to petitioner
    trusts. In the notices of liability respondent identified Davreyn as the transferor
    with an unpaid Federal income tax liability of $4,602,986, plus additions to tax, an
    accuracy-related penalty, fees, and interest, for a total liability of $10,753,478.
    Respondent determined each petitioner trust’s individual transferee liability on the
    basis of the total amount each petitioner trust received in the stock redemption and
    stock sale.27
    27
    Respondent calculated each petitioner trust’s individual transferee liability
    as follows: (1) for the Reynolds Trust, respondent determined transferee liability
    of $2,710,241, consisting of $2,673,431 in cash received and $36,810 in fees paid
    to professional advisers and (2) for each of the Swords Trust, the Mackell Trust,
    (continued...)
    - 27 -
    In attached statements respondent advised petitioner trusts that the IRS did
    not recognize their purported stock sale transactions with Alrey Trust. The
    statements further advised that the amounts petitioner trusts received for the
    purported stock sales would be attributable to them “in liquidation or distribution
    of assets of Davreyn Corporation on or around” February 15, 2001. The
    statements further explained that the purported stock sale transactions were
    “substantially similar to an Intermediary transaction tax shelter described in Notice
    2001-16 and Notice 2008-111.”
    OPINION
    I.    Overview
    These cases involve several transactions which respondent now seeks to
    reconfigure in a way that makes the assets of petitioner trusts a source of
    collection for tax liabilities originally imposed on Alrey Trust and Alrey
    Acquisition. In simple terms, Alrey Trust purchased all of the Davreyn stock from
    petitioner trusts so that it could acquire Davreyn’s then principal asset, Alcoa
    stock. With the benefit of hindsight, it now appears that Alrey Trust and Alrey
    27
    (...continued)
    and the Brotherton Trust, respondent determined transferee liability of $3,833,988,
    consisting of $3,416,891 in cash received, $370,050 attributable to the transfer of
    the membership interests in Davreyn LLC, and $47,047 in fees paid to
    professional advisers.
    - 28 -
    Acquisition were established to participate in a preplanned series of interrelated
    transactions designed to illegitimately avoid tax on Alrey Trust’s sale of
    Davreyn’s Alcoa stock, which it had acquired as a liquidating distribution. Alrey
    Trust sold the Alcoa stock incident to receiving it and reported that the substantial
    gain on the sale was offset by an artificial loss resulting from what appears to have
    been a Son-of-Boss transaction by Alrey Acquisition, the grantor of Alrey Trust.
    After assessing substantial tax liabilities against Alrey Trust, Alrey
    Acquisition, and Davreyn, respondent now contends that petitioner trusts’ sales of
    their Davreyn stock were part of a plan by petitioner trusts to illegitimately avoid
    corporate tax on the distribution of the Alcoa stock in liquidation of Davreyn.
    Respondent contends that his collection of the tax from petitioner trusts is under
    the authority of section 6901. The Commissioner has likewise relied upon that
    section to attempt to collect tax from claimed transferees in other similar cases
    which have recently come before this Court. See, e.g., Hawk v. Commissioner,
    T.C. Memo. 2012-154; Salus Mundi Found. v. Commissioner, T.C. Memo. 2012-
    61, vacated and remanded sub nom. Diebold Found., Inc. v. Commissioner, 
    736 F.3d 172
    (2d Cir. 2013); Slone v. Commissioner, T.C. Memo. 2012-57; Sawyer
    Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, rev’d and remanded,
    
    712 F.3d 597
    (1st Cir. 2013); Feldman v. Commissioner, T.C. Memo. 2011-297,
    - 29 -
    appeal docketed, No. 12-3144 (7th Cir. Sept. 18, 2012); Starnes v. Commissioner,
    T.C. Memo. 2011-63, aff’d, 
    680 F.3d 417
    (4th Cir. 2012). This Court concluded
    in all but one of those cases that the Commissioner’s reliance on section 6901 to
    impose transferee liability upon the claimed transferees was wrong. See Salus
    Mundi Found. v. Commissioner, T.C. Memo. 2012-61 (decisions entered against
    the Commissioner); Slone v. Commissioner, T.C. Memo. 2012-57 (decisions
    entered against the Commissioner); Sawyer Trust of May 1992 v. Commissioner,
    T.C. Memo. 2011-298 (decision entered against the Commissioner); Feldman v.
    Commissioner, T.C. Memo. 2011-297 (decisions entered for the Commissioner);
    Starnes v. Commissioner, T.C. Memo. 2011-63 (decisions entered against the
    Commissioner).28 The Court of Appeals for the Fourth Circuit affirmed our
    judgment in Starnes v. Commissioner, 
    680 F.3d 417
    , but the Courts of Appeals for
    the First and Second Circuits did not do likewise in the Salus Mundi Found. and
    the Sawyer Trust of May 1992 cases. See Diebold Found., Inc. v. Commissioner,
    
    736 F.3d 172
    ; Sawyer Trust of May 1992 v. Commissioner, 
    712 F.3d 597
    . This
    Court subsequently determined upon remand from the Court of Appeals for the
    28
    In Hawk v. Commissioner, T.C. Memo. 2012-154, the Court denied the
    taxpayers’ motion for summary judgment, concluding that genuine issues of
    material fact remained in dispute as to whether they were liable as transferees
    under sec. 6901.
    - 30 -
    First Circuit that the disputed transferee in the Sawyer Trust of May 1992 case was
    liable under section 6901 as a transferee of a transferee but concluded that the
    liability was less than the Commissioner had determined. See Sawyer Trust of
    May 1992 v. Commissioner, T.C. Memo. 2014-59.29 We decide the issue at hand
    with this overview in mind.
    II.   Section 6901(a)
    Section 6901(a) provides that the Commissioner may proceed against a
    transferee of property to assess and collect Federal income tax, penalties, and
    interest owed by the transferor (sometimes collectively, transferor’s unpaid taxes).
    See also sec. 301.6901-1(a), Proced. & Admin. Regs. A transferee under section
    6901 includes, among other persons, a shareholder of a dissolved corporation. See
    sec. 301.6901-1(b), Proced. & Admin. Regs. Section 6901 does not impose
    liability on the transferee but merely gives the Commissioner a procedure to
    collect the transferor’s existing liability. Commissioner v. Stern, 
    357 U.S. 39
    , 42
    (1958).
    29
    This Court has yet to decide Salus Mundi Found. v. Commissioner, T.C.
    Memo. 2012-61, vacated and remanded sub nom. Diebold Found., Inc. v.
    Commissioner, 
    736 F.3d 172
    (2d Cir. 2013), following its remand from the Court
    of Appeals for the Second Circuit.
    - 31 -
    The Commissioner may collect the transferor’s unpaid tax from the
    transferee if an independent basis exists under applicable State law or State equity
    principles for holding the transferee liable for the transferor’s debts. Sec. 6901(a);
    Commissioner v. 
    Stern, 357 U.S. at 45
    ; Hagaman v. Commissioner, 
    100 T.C. 180
    ,
    183 (1993); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op. at 15. State
    law determines the elements of liability, and section 6901 provides the remedy or
    procedure to be employed by the Commissioner as the means of enforcing that
    liability. Ginsberg v. Commissioner, 
    305 F.2d 664
    , 667 (2d Cir. 1962), aff’g 
    35 T.C. 1148
    (1961); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op. at 15.
    The applicable State law is the law of the State where the transfer occurred. See
    Commissioner v. 
    Stern, 357 U.S. at 45
    ; Starnes v. 
    Commissioner, 680 F.3d at 426
    .
    In sum, section 6901 allows the Commissioner to collect a taxpayers’s
    unpaid tax from another person if three conditions are met. First, the taxpayer
    must be liable for the unpaid tax. Second, the other person must be a “transferee”
    within the meaning of section 6901. Third, an independent basis must exist under
    applicable State law or State equity principles for holding the other person liable
    for the taxpayer’s unpaid tax. Accord Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 183-184
    ; Sawyer Trust of May 1992 v. 
    Commissioner, 712 F.3d at 604
    -
    605. Section 6901 does not apply if one or more of these three conditions is not
    - 32 -
    met. Accord Commissioner v. Stern, 
    357 U.S. 39
    ; Diebold Found., Inc. v.
    
    Commissioner, 736 F.3d at 183-184
    ; Sawyer Trust of May 1992 v. 
    Commissioner, 712 F.3d at 604
    -605; Starnes v. 
    Commissioner, 680 F.3d at 430
    .
    III.   Burden of Proof
    Section 6902(a) provides that in this Court the Commissioner bears the
    burden of proving that a person is liable as a transferee. See also Rule 142(a), (d).
    Section 6902(a) further provides that the Commissioner does not bear the burden
    of proving that the transferor was liable for the tax which the Commissioner seeks
    to collect by way of section 6901. See also Rule 142(d); cf. Rule 142(a)(1)
    (generally stating the well-settled rule of Welch v. Helvering, 
    290 U.S. 111
    , 115
    (1933), that the Commissioner’s determinations are presumed to be correct, and
    taxpayers challenging those determinations bear the burden of proving them
    wrong).
    Petitioners argue that notwithstanding section 6902(a), respondent bears the
    burden of proving that Davreyn is liable for the tax determined in the notice of
    deficiency. This is because, petitioners argue, section 7491(a) applies to shift the
    burden of proof on that issue to respondent. Pursuant to section 7491(a), the
    burden of proof shifts to the Commissioner as to any factual issue relevant to a
    taxpayer’s liability for tax where the taxpayer introduces credible evidence with
    - 33 -
    respect to the issue, sec. 7491(a)(1), and the taxpayer satisfies certain other
    conditions, including substantiation of any item and cooperation with the
    Government’s requests for witnesses and information, sec. 7491(a)(2). See also
    Higbee v. Commissioner, 
    116 T.C. 438
    , 440-441 (2001).
    We need not and do not decide whether section 7491(a) applies to shift the
    burden of proof as petitioners desire. This is because, as discussed below, we hold
    that section 6901 does not apply to these cases because the record fails to establish
    that an independent basis exists under applicable State law or State equity
    principles for holding petitioner trusts liable for Davreyn’s unpaid tax and that
    holding would remain the same even if we decided that Davreyn is liable for the
    tax as determined in the notice of deficiency.
    IV.   Parties’ Arguments
    Each party sets forth various arguments in the posttrial briefs. These
    arguments include competing views on whether Davreyn is liable for the tax
    determined in the notice of deficiency and whether petitioner trusts are
    “transferees” within the meaning of section 6901.
    As we previously stated, our holding that section 6901 is inapplicable to
    these cases would remain the same even if we decided that Davreyn is liable for
    the tax determined in the notice of deficiency. The same would be true if we also
    - 34 -
    decided that petitioner trusts are “transferees” within the meaning of section 6901.
    Given that those two issues have no effect on our disposition of these cases, we
    need not and do not decide those issues in this Opinion. We hereinafter assume
    (but do not decide) that Davreyn is liable for the tax as determined in the notice of
    deficiency and that petitioner trusts are “transferees” within the meaning of section
    6901, and we confine our discussion to the parties’ dispute on whether applicable
    State law and/or State equity principles hold petitioner trusts liable for Davreyn’s
    unpaid Federal income tax. See also Commissioner v. 
    Stern, 357 U.S. at 41-42
    ;
    Sawyer Trust of May 1992 v. 
    Commissioner, 712 F.3d at 604
    -605; Starnes v.
    
    Commissioner, 680 F.3d at 427
    , 430.
    Respondent urges the Court to adopt the following two-step analysis to
    determine whether petitioner trusts, as transferees from Davreyn, are liable for
    Davreyn’s unpaid tax: (1) analyze whether the subject transactions are recast
    under Federal law, here primarily the Federal substance over form doctrine, and
    then (2) apply State law to the transactions as recast under Federal law. One or
    more transactions are recast or otherwise disregarded under the Federal substance
    over form doctrine where the transactions, taken as a whole, show that the
    transactions are shams or have no “purpose, substance, or utility apart from their
    anticipated tax consequences.” Goldstein v. Commissioner, 
    364 F.2d 734
    , 740 (2d
    - 35 -
    Cir. 1966), aff’g 
    44 T.C. 284
    (1965); see also Commissioner v. Court Holding Co.,
    
    324 U.S. 331
    (1945); Gregory v. Helvering, 
    293 U.S. 465
    , 469-470 (1935); Rice’s
    Toyota World, Inc. v. Commissioner, 
    752 F.2d 89
    , 95 (4th Cir. 1985), aff’g on this
    issue 
    81 T.C. 184
    (1983). The effect of this doctrine is that the substance and not
    the form of the transactions determines their tax consequences. Commissioner v.
    Court Holding 
    Co., 324 U.S. at 333-334
    ; Gregory v. 
    Helvering, 293 U.S. at 469
    -
    470; Rice’s Toyota World, Inc. v. 
    Commissioner, 752 F.2d at 95
    ; Lazarus v.
    Commissioner, 
    58 T.C. 854
    , 864 (1972), aff’d, 
    513 F.2d 824
    (9th Cir. 1975).
    Alternatively, respondent contends, petitioner trusts, as transferees from Davreyn
    and without regard to the Federal law characterization of the transactions, are
    liable for Davreyn’s debts under applicable State law or State equity principles.
    Petitioner trusts argue that they are not liable for Davreyn’s tax liability because,
    they contend, (1) the transactions may be recast only under applicable State law,
    which does not provide for any such recast, and (2) respondent failed to show that
    they are liable for Davreyn’s debts under applicable State law or State equity
    principles.
    V.    Respondent’s Proposed Two-Step Analysis
    Respondent asks the Court to adopt his referenced two-step analysis of
    transferee liability. We decline to do so. The U.S. Courts of Appeals for the First,
    - 36 -
    Second, and Fourth Circuits have rejected the Commissioner’s requests to apply
    that analysis, see Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 184-185
    ;
    Sawyer Trust of May 1992 v. 
    Commissioner, 712 F.3d at 604
    -605; Starnes v.
    
    Commissioner, 680 F.3d at 428-429
    , and we do likewise. In the earliest appellate
    opinion in that trilogy of cases, the U.S. Court of Appeals for the Fourth Circuit,
    applying Commissioner v. Stern, 
    357 U.S. 39
    , held that the question of whether a
    transfer occurred for purposes of section 6901 was separate from the question of
    whether the transfer was fraudulent for State law purposes and concluded that
    “Stern forecloses the Commissioner’s efforts to recast transactions under federal
    law before applying state law to a particular set of transactions.” Starnes v.
    
    Commissioner, 680 F.3d at 428-429
    . The Courts of Appeals for the First and
    Second Circuits subsequently followed suit espousing similar rationales. See
    Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 185-186
    (rejecting the
    Commissioner’s argument that State law liability is determined on the basis of a
    transaction as recast under Federal law); Sawyer Trust of May 1992 v.
    
    Commissioner, 712 F.3d at 604
    -605;30 accord Ewart v. Commissioner, 
    814 F.2d 30
             In Sawyer Trust of May 1992 v. Commissioner, 
    712 F.3d 597
    , 604 (1st
    Cir. 2013), rev’g and remanding T.C. Memo. 2011-298, the Commissioner argued
    that this Court erred by: (1) failing to apply the Federal substance over form
    doctrine to determine whether the taxpayer was a transferee before analyzing the
    (continued...)
    - 37 -
    321, 324 (6th Cir. 1987) (the court, relying in part on Commissioner v. Stern, 
    357 U.S. 39
    , noted that: (1) section 6901 is a purely procedural statute, and (2) the
    30
    (...continued)
    taxpayer’s liability under State law and (2) failing to find that the taxpayer had
    constructive knowledge of the buyer’s tax avoidance scheme. The U.S. Court of
    Appeals for the First Circuit rejected both arguments. 
    Id. at 604-606.
    The court
    found, however, that this Court failed to analyze whether the taxpayer was liable
    under a provision of the Uniform Fraudulent Transfer Act that provides that a
    transfer is fraudulent “‘if the corporation didn’t receive “reasonably equivalent
    value” in return for the transfer and as a result was left with insufficient assets to
    have a reasonable chance of surviving’”, even if the taxpayer lacked fraudulent
    intent. 
    Id. at 606-607
    (quoting Boyer v. Crown Stock Distrib., Inc., 
    587 F.3d 787
    ,
    792 (7th Cir. 2009)). That court remanded the case to this Court to address that
    issue. 
    Id. at 606-612.
    Here, respondent did not argue in his opening brief that all
    or any part of the subject transactions was fraudulent for lack of the receipt of
    “reasonably equivalent value”. Nor did respondent notify us (or otherwise argue)
    that the court’s opinion in Sawyer Trust of May 1992 v. Commissioner, 
    712 F.3d 597
    , which was released after these cases were fully briefed, was pertinent or
    significant supplemental authority for our consideration of these cases. The
    Commissioner, by contrast, did argue in the Starnes case that a transfer was
    fraudulent for lack of the receipt of reasonably equivalent value. See, e.g., Starnes
    v. Commissioner, 
    680 F.3d 417
    , 430 (4th Cir. 2012), aff’g T.C. Memo. 2011-63.
    In addition, respondent did notify us in these cases that the Court of Appeals for
    the Second Circuit decided Diebold Found., Inc. v. Commissioner, 
    736 F.3d 172
    (2d Cir. 2013), vacating and remanding Salus Mundi Found. v. Commissioner,
    T.C. Memo. 2012-61, after these cases were briefed. See discussion infra note 33.
    Given our additional discussion infra pp. 43-45 that the Sawyer Trust of May 1992
    case involved the Uniform Fraudulent Transfer Act and that Virginia has not
    adopted that act (or its predecessor), and that the thrust of respondent’s argument
    in these cases is that the Federal substance over form doctrine applies with full
    force in determining transferee liability, we conclude that respondent has
    consciously decided to forgo (or has otherwise waived) any argument that all or
    any part of the subject transactions was fraudulent for lack of the receipt of
    “reasonably equivalent value”.
    - 38 -
    question of a taxpayer’s substantive liability is decided on the basis of State law),
    aff’g 
    85 T.C. 544
    (1985).
    This Court has previously never explicitly adopted or rejected respondent’s
    proposed two-step analysis to decide whether a transaction should be recast under
    the Federal substance over form (or similar) doctrine when analyzing whether a
    transferee is liable under section 6901. Our approach, however, has been to
    require that State law allow such a transaction to be recast under a substance over
    form (or similar) doctrine before doing so. See Salus Mundi Found. v.
    Commissioner, slip. op at 25 (“The law of the State where the transfer occurred (in
    these cases, New York) controls the characterization of the transaction.”); Sawyer
    Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 29-30, 34
    (stating that “[t]he law of the State where the transfer occurred (in this case,
    Massachusetts) controls the characterization of the transaction” and “[w]hether the
    transactions should be ‘collapsed’ is a difficult issue of State law on which there is
    fairly limited precedent”); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op.
    at 21-23 (discussing cases addressing whether certain transactions should be
    collapsed under the Uniform Fraudulent Conveyance Acts of the corresponding
    States); see also Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 184
    (stating
    that this Court accepted Diebold’s position that under the Commissioner’s
    - 39 -
    proposed two-step analysis, Federal law may be used to recharacterize a
    transaction to determine whether someone is a transferee, but State law determines
    whether to recharacterize the transaction when analyzing the transferee’s liability).
    Our Memorandum Opinion in Feldman v. Commissioner, T.C. Memo.
    2011-297, does not compel a contrary conclusion. Accord Slone v.
    Commissioner, slip op. at 25 n.9 (describing the facts in Feldman as “unique”).
    The Court in Feldman v. Commissioner, slip op. at 25-37, applied the Federal
    substance over form doctrine to recast a series of transactions and then, without
    further explanation, applied State law to find the taxpayer liable as a transferee
    with respect to the recast transaction. Moreover, unlike here (as discussed below),
    there the Court found that “it is absolutely clear that all individuals involved * * *
    were aware that * * * [the buyer] and its representatives had no intention of ever
    paying the tax liabilities” and that the taxpayer and the buyer’s financing was a
    sham transaction. 
    Id. at 14,
    19.
    VI.   Applicability of State Law
    A.     Overview
    Respondent argues alternatively that petitioner trusts are liable under
    applicable State law and/or State equity principles. In this vein, the parties agree
    that Virginia law is the applicable State law for this purpose. Respondent argues
    - 40 -
    more specifically that the applicable Virginia law is: (1) Va. Code Ann. sec. 55-80
    (2012), which imposes liability on the grounds of actual fraud, (2) Va. Code Ann.
    sec. 55-81 (2012), which imposes liability on the grounds of constructive fraud,
    and (3) Virginia’s trust fund doctrine.
    We address the referenced statutory provisions and doctrine in turn. Before
    doing so, however, we pause briefly to address the scope of the transaction to
    which Virginia law will be applied.
    B.     Scope of Transaction
    Respondent argues primarily that Federal law sets the scope of the
    transaction to which State law is applied. We disagree for the reasons stated
    above. Respondent argues alternatively that Virginia has a substance over form
    doctrine that applies to recast the series of transactions as one transfer between
    each of petitioner trusts and Davreyn. Respondent relies on Burruss Timber Co. v.
    Frith, 
    324 S.E.2d 679
    (Va. 1985), to support his alternative argument that Virginia
    has a substance over form doctrine that applies to these cases.
    Where a decision involves the applicability of State law, as it does here, we,
    as a Federal court, must apply State law in the manner that the highest court of the
    State has indicated that it would apply the law. See Commissioner v. Estate of
    Bosch, 
    387 U.S. 456
    , 465 (1967); Estate of Young v. Commissioner, 110 T.C.
    - 41 -
    297, 300, 302 (1998). If the State’s highest court has not spoken on the subject,
    then we must apply State law as we see it, giving “proper regard” to relevant
    rulings of other courts of the State. Commissioner v. Estate of 
    Bosch, 387 U.S. at 465
    ; see also Estate of Young v. Commissioner, 
    110 T.C. 300
    , 302. We should
    follow an opinion on the subject by an intermediate appellate court of the State,
    unless we conclude that the State’s highest court would decide otherwise. See
    Commissioner v. Estate of 
    Bosch, 387 U.S. at 465
    ; Estate of Young v.
    Commissioner, 
    110 T.C. 302
    .
    In the setting at hand, respondent bears the burden of establishing that the
    Supreme Court of Virginia, that State’s highest Court, would apply a substance
    over form doctrine to recast the series of transactions as a transfer between each of
    petitioner trusts and Davreyn. See Kasishke v. United States, 
    426 F.2d 429
    , 435
    (10th Cir. 1970); Bonney v. Commissioner, 
    247 F.2d 237
    , 239 (2d Cir. 1957)
    (citing Helvering v. Fitch, 
    309 U.S. 149
    , 156 (1940), and Helvering v. Leonard,
    
    310 U.S. 80
    , 86 (1940)), aff’g Towers v. Commissioner, 
    24 T.C. 199
    (1955);
    Dalton v. Commissioner, 
    34 T.C. 879
    , 885 (1960); Farnsworth v. Commissioner,
    
    29 T.C. 1131
    , 1139 (1958), aff’d, 
    270 F.2d 660
    (3d Cir. 1959). Respondent relies
    erroneously on Burruss Timber Co., 
    324 S.E.2d 679
    , to meet that burden. In
    Burruss Timber Co., the court considered whether a real estate broker earned a
    - 42 -
    commission when he helped sell all of the stock of a corporate landowner, rather
    than the specific landowner assets which the broker was hired to sell. The court
    analyzed four similar cases from other jurisdictions and found that in each case,
    the broker accomplished a transaction that was “substantially the equivalent” of
    selling the assets and, consequently, that disallowing the broker commissions in
    those cases would have allowed “form to triumph over substance.” 
    Id. at 681-682.
    The court declined to apply a substance over form doctrine to the transaction in
    Burruss Timber Co. and concluded that the broker was not entitled to a
    commission because the stock sale was not “substantially the equivalent” of the
    assets sale for which he was hired. 
    Id. In Burruss
    Timber Co. and in the cases discussed therein, the courts
    considered the substance of the transaction only with respect to the effect of the
    substance on a third party. The courts did not consider whether, with respect to
    the legal rights and responsibilities of the parties to the transactions (i.e., the buyer
    and the seller), the transactions should be collapsed, recast, or disregarded. The
    Supreme Court of Virginia’s opinion in Burruss Timber Co. offers no guidance on
    whether that court would apply the substance over form doctrine described therein
    to determine the effects of a series of transactions on the actual parties to the
    transactions.
    - 43 -
    Respondent has identified no other Virginia case that applied a substance
    over form or similar doctrine. Nor has respondent argued that the transaction
    should be collapsed under Virginia bankruptcy law.31 While respondent
    references a number of Federal tax cases where a court applied Federal law to
    disregard a transaction, those cases are inapposite in that they apply Federal law
    rather than Virginia State law. Respondent has left us unpersuaded that the
    Supreme Court of Virginia would apply a substance over form analysis to the
    present setting.32 This is especially so given our finding, as discussed herein, that
    petitioner trusts (through their trustees) did not as of the time that their stock was
    sold have (or have reason to have) any inkling that the buyer, or someone related
    31
    In Sawyer Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298,
    slip op. at 34, for example, this Court consulted decisions of bankruptcy courts to
    decide which transaction or combinations of transactions should be considered as
    the relevant transfer for purposes of the Massachusetts Uniform Fraudulent
    Transfer Act. The approach there is supported by the fact that the Uniform
    Fraudulent Transfer Act is based on, and consciously designed to operate in
    accordance with the fraudulent transfer provisions in, the Bankruptcy Code. See
    Prefatory Note, Unif. Fraudulent Transfer Act (1984), 7A (Part II), U.L.A. 4-7
    (2006). As discussed infra p. 45, Virginia has not adopted the Uniform Fraudulent
    Transfer Act.
    32
    Notwithstanding respondent’s citation of a single case from the Supreme
    Court of Virginia, we have independently searched for additional Virginia cases
    that could support a conclusion that the Supreme Court of Virginia would apply a
    substance over form (or similar) doctrine in the setting at hand. We have not
    found any case that would lead us to predict that it would.
    - 44 -
    thereto, was acting to illegitimately avoid the payment of Federal tax. Petitioner
    trusts believed that they were simply entering into a sale of their Davreyn stock
    with a willing buyer.
    We also are unpersuaded that the Supreme Court of Virginia would apply a
    substance over form analysis to the present setting because, as respondent asserts,
    petitioner trusts and/or their representatives had actual or constructive knowledge
    of Alrey Trust’s plan to sell the Alcoa stock and to illegitimately avoid any
    resulting tax liability. Simply put, the record at hand does not lead us to find that
    assertion as a fact. Cf. Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 187
    -
    190 (court concluded that shareholders had knowledge of illegitimate plan). After
    these cases were briefed, the Court of Appeals for the Second Circuit decided
    Diebold Found., Inc. v. Commissioner, 
    736 F.3d 172
    . There, the court collapsed
    the series of transactions and found that there was a conveyance under the
    applicable State statute, the New York Uniform Fraudulent Conveyance Act,
    because, the court concluded, the taxpayers constructively knew of the entire
    scheme to illegitimately avoid tax. 
    Id. at 187-190.
    Neither party has requested
    additional briefing in these cases in the light of Diebold Found., Inc.,33 and we
    33
    Respondent filed a notice of supplemental authority referencing Diebold
    Found., Inc. v. Commissioner, 
    736 F.3d 172
    , and petitioners responded to that
    (continued...)
    - 45 -
    conclude that Diebold Found., Inc. is factually distinguishable from these cases for
    three reasons. First, while New York law reflects an adoption of the Uniform
    Fraudulent Conveyance Act, Virginia has not adopted that act (or its successor the
    Uniform Fraudulent Transfer Act) for the relevant period. See Grupo Mexicano
    de Desarrollo, S.A. v. Alliance Bond Fund, Inc., 
    527 U.S. 308
    , 324 n.7 (1999);
    Zazzali v. Swenson (In re DBSI, Inc., 
    463 B.R. 709
    , 718-719 (Bankr. D. Del.
    2012); In re Best Prods. Co.), 
    168 B.R. 35
    , 52 (Bankr. S.D.N.Y. 1994). See
    generally Isaac A. McBeth & Landon C. Davis III, “Bulls, Bears, and Pigs:
    Revisiting the Legal Minefield of Virginia Fraudulent Transfer Law”, 46 U. Rich.
    L. Rev. 273, 274 n.8 (2011-2012); 
    id. at 276,
    293 (stating that “as a general matter,
    the provisions of the UFTA provide greater protection to creditors than Virginia’s
    fraudulent transfer statutes” and analyzing “the UFTA provisions in comparison to
    their Virginia counterparts and the UFTA provisions that have no Virginia
    counterparts, so as to identify differences between the two bodies of fraudulent
    transfer law”). Second, we are unaware of (and respondent has not cited) a
    33
    (...continued)
    notice. Respondent acknowledged in his notice that the relevant State laws in
    Diebold Found., Inc. and in these cases are different (New York and Virginia,
    respectively) and made no attempt to harmonize the relevant New York law with
    Virginia law. Petitioners agree that the relevant laws are different and conclude
    further that the laws are irreconcilable.
    - 46 -
    Virginia case that applies a collapsing doctrine similar to the New York doctrine
    applied in Diebold Found., Inc. Third, even if respondent relied upon such a
    doctrine, we find, contrary to the setting in Diebold Found., Inc., that neither
    petitioner trusts nor their representatives knew (either actually or constructively)
    of a scheme to avoid the tax liability in issue.34
    As to the third point, respondent invites the Court to conclude that petitioner
    trusts were knowing participants in planning the series of transactions that
    respondent maintains included the sale by petitioner trusts of Davreyn stock and
    that they therefore are liable for the unpaid tax resulting from the plan. We
    decline that invitation. In fact, the testimony of Ms. Swords, Ms. Mackell, and
    34
    The third point also persuades us that the Supreme Court of Virginia
    would not collapse the transactions at issue in accordance with a certain rationale
    espoused in LaRosa v. LaRosa, 482 Fed. Appx. 750, 
    2012 WL 1499522
    (4th Cir.
    2012), and Starnes v. Commissioner, 
    680 F.3d 417
    . In LaRosa, 482 Fed. Appx. at
    755 n.3, the court noted in its application of West Virginia law that a court may
    collapse a series of transactions into a single integrated transaction. The court
    cited Official Comm. of Unsecured Creditors of Sunbeam Corp. v. Morgan
    Stanley & Co. (In re Sunbeam Corp.), 
    284 B.R. 355
    , 370 (Bankr. S.D.N.Y. 2002),
    which stands for the proposition that a series of transactions may be collapsed if
    the transactions were linked and the transferee had actual or constructive
    knowledge of the entire scheme. LaRosa, 482 Fed. Appx. 750. In Starnes v.
    
    Commissioner, 680 F.3d at 433
    , the court, in applying North Carolina law, stated
    that in deciding whether to collapse transactions in transferee liability cases, the
    question is whether the taxpayer had actual or constructive knowledge that the
    sold corporation would become delinquent on its taxes. We also note that the
    relevant law in LaRosa and Starnes was that of West Virginia and North Carolina,
    respectively, while the relevant law here is that of Virginia.
    - 47 -
    Ms. Brotherton convinces us to make contrary findings; i.e., that there was no plan
    by petitioner trusts to illegitimately avoid tax, that petitioner trusts had neither
    actual nor constructive knowledge of Alrey Trust’s plan to sell the Alcoa stock
    and to illegitimately avoid any resulting tax liability, that petitioner trusts were not
    aware of circumstances that should have led them to make further inquiry
    regarding Alrey Trust’s postclosing plans, and that petitioner trusts had neither
    actual nor constructive knowledge that Alrey Trust would cause Davreyn to
    become delinquent on its taxes. The testimony of Ms. Swords, Ms. Mackell, and
    Ms. Brotherton emphasized that they were unaware of the financial buyer’s
    identity and the reasons a financial buyer would want to purchase Davreyn’s stock
    and that they relied on the advice of their accountants and lawyers. Ms. Swords,
    Ms. Mackell, and Ms. Brotherton each testified that they did not previously try to
    sell or liquidate Davreyn. Ms. Mackell testified that petitioner trusts did not
    consider selling Davreyn until Mr. Griffin and Mr. Rohman approached petitioner
    trusts in 2000 regarding the potential sale of their Davreyn stock. Ms. Swords and
    Ms. Mackell both testified that petitioner trusts sold their Davreyn stock to Alrey
    Trust on the basis of their advisers’ recommendation. Ms. Swords, Ms. Mackell,
    and Ms. Brotherton repeatedly emphasized their complete trust in their advisers,
    particularly Mr. Griffin. Ms. Swords, Ms. Mackell, and Ms. Brotherton each
    - 48 -
    testified that they did not know the identity of Davreyn’s buyer and that they were
    not aware that the buyer planned to sell Davreyn’s Alcoa stock and/or dissolve
    Davreyn. We find all of this testimony to be credible.
    In addition, as to the potential tax consequences of liquidating Davreyn
    rather than selling its stock, Ms. Brotherton testified that it was not advantageous
    for petitioner trusts to liquidate Davreyn because doing so would subject her, Mr.
    Reynolds, and Ms. Swords and Ms. Mackell to two levels of taxation. Ms.
    Mackell testified further that she and her sisters did not consider liquidating
    Davreyn because they knew petitioner trusts would incur significant tax liabilities.
    Again, we find this testimony to be credible.
    In Slone v. Commissioner, slip op. at 23-24, the Court concluded that the
    taxpayer was aware of the target corporation’s tax liabilities with respect to the
    asset sale and that the acquiring corporation planned to offset gains resulting from
    the asset sale. The taxpayer was unaware, however, that the acquiring corporation
    planned to offset gains through an illegitimate scheme. 
    Id. Here, Ms.
    Swords,
    Ms. Mackell, and Ms. Brotherton did not know that Alrey Trust planned to sell the
    Alcoa stock and generate a significant tax liability, and they were unaware that
    Alrey Trust, through Alrey Acquisition, planned to offset any tax liability with
    respect to Davreyn and/or to its assets.
    - 49 -
    Respondent emphasizes the fact that Mr. Rohman referred to the buyer’s
    “peculiar tax situation” in a memorandum to Ms. Swords, Ms. Mackell, and Ms.
    Brotherton. Respondent asks us to infer from this single phrase that petitioner
    trusts were aware of Alrey Acquisition’s plan to illegitimately avoid the payment
    of tax on the Alcoa stock sale gain. We are not prepared to draw such an
    inference. Mr. Rohman testified that he included this phrase as a reference to the
    fact that the buyer had losses or anticipated generating losses. As this Court noted
    in Sawyer Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at
    37, 45, and in Slone v. Commissioner, slip op. at 24, legitimate transactions may
    be available to offset built-in gain, if recognized, and a taxpayer may contemplate
    the execution of such a transaction. Accordingly, we will not infer from Mr.
    Rohman’s use of the phrase “peculiar tax situation” that petitioner trusts were
    aware of the details of Alrey Trust’s tax situation or that petitioner trusts knew
    about, and agreed to facilitate, an illegal tax avoidance scheme. Because
    petitioner trusts did not know of, approve, or have reason to suspect the multistep
    plan by Alrey Acquisition and related entities to liquidate Davreyn, to sell the
    Alcoa stock, and to attempt to illegitimately avoid the tax on that sale by engaging
    in what likely was a Son-of-Boss transaction involving BMY stock, we decline to
    reconfigure the sale by petitioner trusts of their Davreyn stock as respondent
    - 50 -
    contends we should. We find to the contrary that petitioner trusts had no plan to
    enable Davreyn, Alrey Trust, or Alrey Acquisition to illegitimately avoid tax and
    that they engaged in an arm’s-length sale of Davreyn’s stock. Accord Sawyer
    Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 44-45.
    Respondent contends that even if we conclude (which we do) that petitioner
    trusts and their trustees had no plan to enable Davreyn, Alrey Trust, and/or Alrey
    Acquisition to illegitimately avoid tax, petitioner trusts, through their
    representatives Mr. Griffin and Mr. Rohman, knew that Alrey Trust planned to
    offset the gain from the Alcoa stock sale and that the offset was the reason Alrey
    Trust was interested in purchasing Davreyn. The record does not support this
    contention, and we decline to find it as a fact. Neither Ms. Swords, Ms. Mackell,
    nor Ms. Brotherton has a background in business or in tax, and we find that given
    their lack of business experience, it was not unreasonable for them to rely on the
    advice of their representatives that the stock sale transaction constituted a
    legitimate transaction. See, e.g., Starnes v. 
    Commissioner, 680 F.3d at 436-437
    .
    Moreover, we are not persuaded that any of the representatives knew (either
    actually or constructively) of the plan to illegitimately avoid tax on the Alcoa
    stock sale. Mr. Griffin credibly testified that he did not know the identity of the
    buyer or why the buyer wanted to purchase Davreyn stock. He testified that he did
    - 51 -
    not discuss the buyer’s identity or tax situation with Mr. Rohman. Mr. Griffin also
    testified that at the time of the sale, he did not know that the buyer was planning to
    liquidate Davreyn or that the buyer planned to sell Davreyn’s Alcoa stock to
    Deutsche Bank.
    Mr. Rohman’s testimony about the state of his knowledge is not quite so
    satisfying; he openly acknowledged that he did not know or inquire as to why ICA
    wanted to acquire PHCs like Davreyn. To his credit, however, he also testified
    that he understood that the buyer had losses or anticipated losses. He apparently
    came to this understanding on the basis of a conversation that took place before
    the closing with Mr. Glazman, Mr. Gottlieb, or Mr. Teig. While Mr. Rohman
    assumed that the buyer would want to offset these losses with gain, he testified
    that he was not given any information regarding the buyer’s losses and that he had
    no reason to question the legitimacy of the buyer’s losses. In addition, while Mr.
    Rohman had structured previous sales similar to the transactions at issue, the
    record does not persuade us that he knew that any of the buyers in those
    transactions would cause the PHC to liquidate its stock and attempt to
    illegitimately avoid Federal income tax that would be imposed as to the stock.
    While the lack of due diligence by Mr. Rohman with respect to the buyer’s
    identity and reputation is problematic, he adequately explained to us that he
    - 52 -
    trusted ICA because ICA was represented by a good national law firm and a
    respected international accounting firm and First Union, Alrey Trust’s trustor, was
    a reputable financial institution. He also persuaded us that petitioner trusts had no
    plan to undertake any steps except to sell Davreyn’s stock to the buyer.
    This Court in other transferee liability cases has considered similar
    arguments regarding the knowledge of the taxpayer seller’s representatives and
    has rejected them where the evidence was insufficient to prove that the taxpayer
    seller knew of the buyer’s plan to illegitimately avoid tax. In Slone v.
    Commissioner, slip op. at 23-24, for example, the taxpayers’ attorney sent a
    memorandum to another of the taxpayers’ attorneys, explaining that the buyer
    planned to offset the gain from the sale of the purchased corporation’s assets by
    contributing to the nominal buyer assets with a high basis and low value, then
    selling those assets at a loss before the end of the taxable year. The Court
    concluded that this memorandum was insufficient to show that the taxpayers knew
    of the corporate buyer’s illegitimate scheme. 
    Id. at 24.
    It is clear from Mr. Rohman’s testimony that he at least suspected that the
    buyer would sell the Alcoa stock and offset the gain from that sale with other
    losses. It is likely that Mr. Griffin, an educated tax professional, also considered
    such a possibility. There is no credible evidence, however, that either petitioner
    - 53 -
    trusts or their representatives knew about any plan on the part of the buyer to
    illegitimately avoid the payment of tax on the sale of Davreyn’s Alcoa stock, and
    the representatives’ knowledge that an unrelated buyer planned to offset any gain
    from a sale of the Alcoa stock with incurred or anticipated losses is insufficient to
    show the existence of a preconceived plan by petitioner trusts to illegitimately
    avoid tax. This Court has acknowledged that there are legitimate tax planning
    strategies involving built-in gains and losses and that it was not unreasonable, in
    the absence of contradictory information, for the representatives to believe that the
    buyer had a legitimate tax planning method. See 
    id. at 24;
    Sawyer Trust of May
    1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 37, 45. We find that
    while Mr. Rohman and Mr. Griffin knew or had reason to believe that the buyer of
    petitioner trusts’ stock had tax attributes that made the purchase of the stock
    attractive, Mr. Rohman and Mr. Griffin did not know or have reason to know that
    any such tax attributes were improper or that the buyer intended to liquidate
    Davreyn and to illegitimately avoid any resulting tax liability.35 We also find that
    35
    We are not unmindful of Notice 2001-16, 2001-1 C.B. 730, which was
    released on January 19, 2001, and was formerly published in the Internal Revenue
    Manual on February 26, 2001. The stock sale transaction at issue occurred on
    February 15, 2001, after the release date but before the publication date. While
    Mr. Griffin and Mr. Rohman were aware of this notice, they credibly explained to
    us that they did not believe that it pertained to the Davreyn transaction. We also
    (continued...)
    - 54 -
    neither Mr. Rohman nor Mr. Griffin was aware of any circumstance that would
    have caused him to inquire further into the circumstances of the transaction, which
    Mr. Rohman considered to be a simple stock sale.36
    In sum, we reject respondent’s contention that the transactions at issue
    should be recast by applying a Virginia substance over form doctrine and decline
    to collapse the transactions into a single integrated transaction. Instead, we find
    on the basis of the record at hand that the sale by petitioner trusts of the Davreyn
    stock to Alrey Trust was in form and in substance a sale of stock and that the
    35
    (...continued)
    note that this Court has declined to find taxpayers liable as transferees with respect
    to similar transactions where the transaction occurred both before issuance of
    Notice 
    2001-16, supra
    , see Salus Mundi Found. v. Commissioner, T.C. Memo.
    2012-61, and after its issuance, see Starnes v. Commissioner, T.C. Memo. 2011-
    63.
    36
    In Diebold Found., Inc. v. 
    Commissioner, 736 F.3d at 188
    , the Court of
    Appeals for the Second Circuit concluded that this Court erred in finding that the
    taxpayers’ representatives were not required to make further inquiry into the
    circumstances of the transaction. To that end, the Court noted that the taxpayers
    were sophisticated and well-represented persons who recognized the significant
    tax liability arising from the built-in gains and specifically sought out multiple
    persons to help them minimize that liability. 
    Id. The court
    also noted that the
    taxpayers’ representatives “had a sophisticated understanding of the structure of
    the entire transaction” and had actively participated in implementing the
    transaction. 
    Id. at 188-189.
    The case of Diebold Found., Inc. is factually
    distinguishable from these cases as to this point. Or put differently, respondent
    has simply not persuaded us that a reasonably diligent person in the setting at hand
    would have inquired further into whether Davreyn was going to pay its Federal tax
    for FYE February 15, 2001. Cf. Starnes v. 
    Commissioner, 680 F.3d at 433
    -437.
    - 55 -
    transaction should not be recast as a sale of assets followed by a distribution in
    liquidation. We proceed to evaluate each relevant transaction separately to decide
    whether petitioner trusts are liable as transferees under Virginia law.
    C.     Actual Fraud: Va. Code Ann. Sec. 55-80 (2012)
    We begin our evaluation with Va. Code Ann. sec. 55-80, which provides:
    Every gift, conveyance, assignment or transfer of, or charge
    upon, any estate, real or personal, every suit commenced or decree,
    judgment or execution suffered or obtained and every bond or other
    writing given with intent to delay, hinder or defraud creditors,
    purchasers or other persons of or from what they are or may be
    lawfully entitled to shall, as to such creditors, purchasers or other
    persons, their representatives or assigns, be void. This section shall
    not affect the title of a purchaser for valuable consideration, unless it
    appear that he had notice of the fraudulent intent of his immediate
    grantor or of the fraud rendering void the title of such grantor.
    The person seeking to set aside a conveyance as a fraudulent conveyance under
    this section must prove that (1) “the transfer was made with the intent to delay,
    hinder or defraud creditors” and (2) “the transferee had notice of the transferor’s
    intent to defraud.” Coleman v. Cmty. Trust Bank, N.A. (In re Coleman), 
    299 B.R. 780
    , 795 (W.D. Va. 2003), aff’d in part, rev’d in part and remanded on other
    issues, 
    426 F.3d 719
    (4th Cir. 2005). A transferee’s fraudulent intent must be
    proved with clear and convincing evidence. See Armstrong v. United States, 7 F.
    Supp. 2d 758, 764 (W.D. Va. 1998).
    - 56 -
    Because it is difficult to prove fraudulent intent by direct evidence, fraud
    may be established by circumstantial evidence, which includes various “badges of
    fraud”. See 
    id. These badges
    include: “(1) the close relationship of the parties,
    (2) the grantor’s insolvency, (3) pursuit of the grantor by creditors at the time of
    the transfer, (4) inadequate consideration, * * * (5) retention of possession of the
    property by the grantor”, 
    id., and (6)
    “fraudulent incurrence of indebtedness after
    the conveyance”, In re Porter, 
    37 B.R. 56
    , 63 (Bankr. E.D. Va. 1984).
    Respondent contends that Davreyn transferred to petitioner trusts its assets
    and cash in liquidation and petitioner trusts are substantively liable for Davreyn’s
    unpaid tax because the transfer was fraudulent under Virginia law. Petitioners
    contend that respondent erroneously collapsed a series of transactions into a single
    transfer. Petitioners further contend that because there was no fraudulent transfer
    from Davreyn to petitioner trusts, petitioner trusts cannot be liable as transferees
    of Davreyn under Virginia law. We agree with petitioners.
    With the exception of Davreyn’s ownership interest in Davreyn LLC, which
    was transferred to petitioner trusts through a redemption transaction which was not
    fraudulent, Davreyn did not transfer anything to petitioner trusts. The sales of
    Davreyn stock occurred between petitioner trusts and Alrey Trust. Accordingly,
    - 57 -
    the relevant inquiry must focus on the value of the consideration petitioner trusts
    exchanged with Alrey Trust.
    Alrey Trust paid petitioner trusts a total of $13,102,055 in exchange for
    their Davreyn stock. Alrey Trust did not use Davreyn’s cash or its assets to
    purchase the stock from petitioner trusts; instead, it borrowed the funds from a
    third-party lender, Integrated Holdings. Davreyn was solvent at the time of the
    stock sale transactions between petitioner trusts and Alrey Trust. At that time
    Davreyn’s only outstanding tax liability related to the redemption transaction and
    Davreyn had sufficient assets to pay its tax liability. We decline to find that any
    transfer meeting the requirements of Va. Code Ann. sec. 55-80 occurred between
    petitioner trusts and Davreyn or Alrey Trust.
    D.     Constructive Fraud
    We turn to Va. Code Ann. sec. 55-81, which provides:
    Every gift, conveyance, assignment, transfer or charge which is
    not upon consideration deemed valuable in law, or which is upon
    consideration of marriage, by an insolvent transferor, or by a
    transferor who is thereby rendered insolvent, shall be void as to
    creditors whose debts shall have been contracted at the time it was
    made, but shall not, on that account merely, be void as to creditors
    whose debts shall have been contracted or as to purchasers who shall
    have purchased after it was made. Even though it is decreed to be
    void as to a prior creditor, because voluntary or upon consideration of
    marriage, it shall not, for that cause, be decreed to be void as to
    subsequent creditors or purchasers.
    - 58 -
    The person seeking to set aside a transfer under this section must show that: (1) a
    transfer occurred, (2) the transfer was not supported by valuable consideration,
    and (3) “‘the transfer was done when the transferor was insolvent or the transfer
    rendered the transferor insolvent.’” Smith v. Porter (In re Carr & Porter, LLC),
    
    416 B.R. 239
    , 260 (Bankr. E.D. Va. 2009) (quoting Wu v. Tseng, Nos. 2:06cv346,
    2:06cv580, at *6 (E.D. Va. Jan. 24, 2007)). “[T]here must be a showing of
    indebtedness existing at the time of the transaction.” 
    Id. (citing C.F.
    Trust v.
    Peterson, No. 1:97-CV-2003, 
    1999 WL 33456231
    , at *10 (E.D. Va. Jan. 8, 1999));
    see also In re 
    Porter, 37 B.R. at 65
    .
    The only asset Davreyn conveyed directly to petitioner trusts was its
    ownership interest in Davreyn LLC, which held the Goldman Sachs fund shares.
    However, this conveyance occurred before the stock sale transaction and did not
    render Davreyn insolvent.
    At the time petitioner trusts sold their Davreyn stock to Alrey Trust,
    Davreyn was solvent, possessing assets in excess of $14 million, and owed a tax
    liability of $37,500 (the tax liability that arose in connection with the redemption
    transaction). Alrey Trust paid a total of $13,102,055 to petitioner trusts in
    exchange for Davreyn’s stock. In calculating the amount owed to petitioner trusts,
    the parties to the stock sale left sufficient cash in Davreyn to pay the $37,500 tax
    - 59 -
    liability from the redemption transaction. We find no constructive fraud on this
    record.37
    E.     Virginia’s Trust Fund Doctrine
    We now turn to respondent’s contention that petitioner trusts are liable
    under Virginia’s trust fund doctrine. In Marshall v. Fredericksburg Lumber Co.,
    
    173 S.E. 553
    , 557 (Va. 1934), the Supreme Court of Appeals of Virginia stated:
    But where there are existing creditors of a corporation the
    stockholders will not be permitted, as against those creditors, to
    withdraw the assets of the corporation without consideration, whether
    it be done through a purchase of stock by the corporation or
    otherwise. We repeat that a stockholder is not entitled to a share of
    the capital assets of a corporation until the debts have been paid. * * *
    In 
    Marshall, 173 S.E. at 557-558
    , the corporation received no consideration for its
    assets. The court emphasized that the transaction at issue was negotiated by the
    corporation’s president, who was obligated “to conserve the assets of the
    corporation and have them forthcoming for the purpose, primarily, of paying
    corporation debts.” 
    Id. at 558.
    In Ashworth v. Hagan Estates, Inc., 
    181 S.E. 381
    ,
    385 (Va. 1935), the Supreme Court of Appeals of Virginia quoted with approval a
    37
    The series of transactions designed to illegitimately avoid tax occurred
    immediately after petitioner trusts sold their Davreyn stock to Alrey Trust. Those
    transactions were planned and orchestrated by Alrey Trust and Alrey Acquisition
    (and not petitioner trusts), and petitioner trusts had neither actual nor constructive
    knowledge of those transactions or their purpose.
    - 60 -
    Supreme Court of Oregon case stating that the concepts of the trust fund doctrine
    apply “where a corporation transfers all its assets to another corporation with a
    view of going out of business, and nothing is left with which to pay its debts”.
    Mr. Griffin and Ms. Swords, Ms. Brotherton, and Ms. Mackell did not take
    any actions constituting a winding up or dissolution of Davreyn while serving as
    the officers and directors of Davreyn. See Starnes v. Commissioner, T.C. Memo.
    2011-63, slip op. at 31-32 (applying North Carolina’s trust fund doctrine in a
    transferee liability case). When petitioner trusts sold their Davreyn stock, neither
    petitioner trusts nor their representatives knew that Alrey Trust planned to
    dissolve Davreyn. When Alrey Trust dissolved Davreyn, Mr. Austin was serving
    as Davreyn’s sole director, and no one associated with petitioner trusts had any
    role in structuring the sale of the Alcoa stock or in deciding to dissolve Davreyn.
    Petitioner trusts had no interest in Davreyn when Alrey Trust dissolved it because
    they had already sold all of their Davreyn stock.
    Davreyn was not insolvent when petitioner trusts sold their Davreyn stock.
    Neither petitioner trusts nor Davreyn’s directors attempted to avoid any existing
    debt of Davreyn. We decline to find on this record that petitioner trusts or
    Davreyn’s directors took any actions before or at the time of the Davreyn stock
    sale that would support the application of Virginia’s trust fund doctrine.
    - 61 -
    VII. Conclusion
    Respondent has failed to establish that an independent basis exists under
    applicable State law or State equity principles for holding petitioner trusts liable
    for Davreyn’s unpaid tax. Accordingly, we hold that section 6901 does not apply
    to these cases. We have considered the parties’ remaining arguments, and to the
    extent not discussed above, conclude those arguments are irrelevant, moot, or
    without merit.
    To reflect the foregoing,
    Decisions will be entered for
    petitioners.
    

Document Info

Docket Number: 10882-10, 10883-10, 10884-10, 10885-10

Citation Numbers: 142 T.C. No. 19

Filed Date: 5/29/2014

Precedential Status: Precedential

Modified Date: 10/30/2014

Authorities (22)

Commissioner v. Court Holding Co. , 65 S. Ct. 707 ( 1945 )

Hyman v. Porter (In Re Porter) , 1984 Bankr. LEXIS 6472 ( 1984 )

Boyer v. Crown Stock Distribution, Inc. , 587 F.3d 787 ( 2009 )

In Re Best Products Co., Inc. , 1994 Bankr. LEXIS 787 ( 1994 )

Smith v. Porter (In Re Carr & Porter, LLC) , 2009 Bankr. LEXIS 979 ( 2009 )

Zazzali Ex Rel. DBSI Estate Litigation Trust v. Swenson (In ... , 463 B.R. 709 ( 2012 )

simon-m-lazarus-v-commissioner-of-internal-revenue-mina-lazarus-v , 513 F.2d 824 ( 1975 )

gertrude-a-farnsworth-and-gertrude-adams-farnsworth-james-d-carpenter , 270 F.2d 660 ( 1959 )

Theodore C. Bonney v. Commissioner of Internal Revenue , 247 F.2d 237 ( 1957 )

Kapel Goldstein and Tillie Goldstein v. Commissioner of ... , 364 F.2d 734 ( 1966 )

Robert Ginsberg v. Commissioner of Internal Revenue , 305 F.2d 664 ( 1962 )

Grupo Mexicano De Desarrollo, S. A. v. Alliance Bond Fund, ... , 119 S. Ct. 1961 ( 1999 )

Rice's Toyota World, Inc. (Formerly Rice Auto Sales, Inc.) ... , 752 F.2d 89 ( 1985 )

in-re-molly-jane-coleman-debtor-roger-coleman-and-molly-jane-coleman , 426 F.3d 719 ( 2005 )

Albert Henry Kasishke, Jr., of the Estate of Olive M. ... , 426 F.2d 429 ( 1970 )

Helvering v. Leonard , 60 S. Ct. 780 ( 1940 )

Official Committee of Unsecured Creditors of Sunbeam Corp. ... , 2002 Bankr. LEXIS 1183 ( 2002 )

Coleman v. Community Trust Bank, N.A. (In Re Coleman) , 92 A.F.T.R.2d (RIA) 7145 ( 2003 )

Gregory v. Helvering , 55 S. Ct. 266 ( 1935 )

Helvering v. Fitch , 60 S. Ct. 427 ( 1940 )

View All Authorities »