Blum v. Comm'r , 103 T.C.M. 1099 ( 2012 )


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  •                   T.C. Memo. 2012-16
    UNITED STATES TAX COURT
    SCOTT A. AND AUDREY R. BLUM, Petitioners v.
    COMMISSIONER OF INTERNAL REVENUE, Respondent
    Docket No. 2679-06.              Filed January 17, 2012.
    Ps, through a grantor trust, entered into an
    Offshore Portfolio Investment Strategy (OPIS)
    transaction through KPMG, an accounting firm. Through
    direct and indirect interests in UBS stock, they
    created a $45 million loss. Ps claimed the loss for
    tax purposes but did not, in fact or substance, incur a
    $45 million loss. Ps were pursued by KPMG when KPMG
    became aware that Ps would have a substantial capital
    gain. KPMG issued an opinion, after the fact, that the
    $45 million capital loss would “more likely than not”
    be upheld.
    1. Held: the OPIS transaction is disregarded
    under the economic substance doctrine.
    2. Held, further, Ps are liable for accuracy-
    related penalties for gross valuation misstatements and
    negligence under sec. 6662(a), I.R.C.
    -2-
    Nancy Louise Iredale, Jeffrey Gabriel Varga, and Stephen J.
    Turanchik, for petitioners.
    Henry C. Bonney, Jr., Kevin G. Croke, and Elizabeth S.
    Martini, for respondent.
    MEMORANDUM FINDINGS OF FACT AND OPINION
    KROUPA, Judge:    Respondent determined deficiencies in and
    penalties with respect to petitioners’ Federal income taxes for
    1998, 1999 and 2002 (years at issue) as follows:
    Penalties
    Year      Deficiency       Sec. 6662(b)    Sec. 6662(h)
    1998      $9,414,861          $1,948          $3,762,048
    1999      16,298,672           2,954           6,513,560
    2002          18,737           3,747              -0-
    The parties have resolved a number of issues in their stipulation
    of settled issues.    In addition, the Court dismissed for lack of
    jurisdiction those portions of the deficiencies and penalties
    pertaining to petitioners’ Bond Leveraged Investment Portfolio
    Strategy (BLIPS) transaction.   Accordingly, the parties will need
    to prepare a Rule 1551 computation.
    This Court has not previously considered an Offshore
    Portfolio Investment Strategy (OPIS) transaction.    The question
    1
    All section references are to the Internal Revenue Code
    (Code) for the years at issue, and all Rule references are to the
    Tax Court Rules of Practice and Procedure, unless otherwise
    indicated. All monetary amounts are rounded to the nearest
    dollar.
    -3-
    before us is whether petitioners are entitled to deduct certain
    capital losses claimed from their participation in the OPIS
    transaction.    We hold that they are not because the transaction
    lacks economic substance.    We must also decide whether
    petitioners are liable for gross valuation misstatement penalties
    and negligence penalties under section 6662(a).    We hold they are
    liable for the penalties.
    FINDINGS OF FACT
    Some of the facts have been stipulated and are so found.      We
    incorporate the stipulation of facts and documents, the second
    stipulation of facts and documents, the third stipulation of
    documents and the accompanying exhibits by this reference.
    Petitioners resided in Jackson, Wyoming when they filed the
    petition.
    I. Petitioners’ Background
    Scott Blum (Mr. Blum) and Audrey Blum (Mrs. Blum) were
    married in the mid-1990s and have twin children.    Mr. Blum, the
    only adopted child of an engineer and a secretary, was an
    entrepreneurial child and prone to selling his toys.    After
    parking cars for a hotel and selling women’s shoes, he started
    his first company when he was 19 years old to sell computer
    memory products.    He sold that company two years later for over
    $2 million.    During the same year, at the age of 21, Mr. Blum
    started Pinnacle Micro, Inc. (Pinnacle) with his parents.    Mr.
    Blum and his parents ran Pinnacle for nine years, including when
    -4-
    it was a public company.   Mr. Blum entered into an Internet-based
    business after leaving Pinnacle.
    Mr. Blum founded Buy.com, an online retailer, in 1997, and
    it set a record for being the fastest growing company in United
    States history during its first year of operation.    In 1998 Mr.
    Blum sold a minority interest in Buy.com stock for a total of $45
    million.   The sales comprised a $5 million stock sale in August
    and a $40 million stock sale at the end of September.    His basis
    in the stock was zero, and in response to the potential gain Mr.
    Blum entered into a $45 million OPIS transaction during 1998,
    creating a capital loss of approximately $45 million.    The OPIS
    transaction was created, managed and promoted by Mr. Blum’s
    accounting firm.
    Mr. Blum, a savvy businessman, has relied on advisers
    including accountants, attorneys and investment counselors.      He
    never prepared his own tax return.    We will introduce the
    participants in the OPIS transaction and the entities used to set
    up the transaction before describing the arrangement.
    II. The Participants
    A. The Blum Trust
    Mr. Blum created the Scott A. Blum Separate Property Trust
    (Blum Trust) in 1995 as a grantor trust.    A grantor trust is
    disregarded as an entity for Federal income tax purposes.     The
    Blum Trust was established near the time of Mr. Blum’s marriage
    -5-
    for family financial planning purposes to address the possibility
    of a divorce and its effect upon his corporate businesses.    The
    Blum Trust normally held stock in Mr. Blum’s start-up companies
    and has held other investments through stock brokerage firms.
    B. KPMG
    Petitioners’ accountant, KPMG Peat Marwick LLP (KPMG),2 a
    “Big Four” tax and accounting firm, prepared their individual tax
    returns.   KPMG also represented petitioners in a Federal income
    tax audit, and Mr. Blum hired KPMG employees to work for him as
    his business employees.
    KPMG is a member firm of KPMG International, a Swiss
    cooperative, of which all KPMG firms worldwide are members.   At
    all relevant times, KPMG was one of the largest accounting firms
    in the world, providing services to many of the largest
    corporations worldwide.   KPMG provided tax services to corporate
    and individual clients, including preparing tax returns,
    providing tax planning and tax advice and representing clients
    before the Internal Revenue Service and the U.S. Tax Court.
    In 1998 KPMG was promoting a transaction commonly referred
    to as OPIS.    KPMG’s capital transaction group sought clients with
    large capital gains (above a certain dollar threshold) for the
    OPIS transaction.   Brent Law (Mr. Law) referred petitioners to
    2
    The firm’s name was later reduced by removing “Peat
    Marwick.”
    -6-
    KPMG's capital transaction group.      Mr. Law had represented
    petitioners in their audit and had prepared their tax returns.
    Mr. Law knew that Mr. Blum had potential capital gains from sales
    of Buy.com stock.    He therefore suggested to Mr. Blum’s financial
    adviser (Mr. Williams) that they contact KPMG’s capital
    transaction group to structure Mr. Blum’s stock sales.      Days
    later, Mr. Blum or Mr. Williams contacted Mr. Law and asked to be
    introduced to Carl Hasting (Mr. Hasting) of KPMG’s capital
    transaction group.
    Mr. Hasting explained the OPIS transaction to Mr. Blum
    without providing any written materials.      Despite the magnitude
    of the investment, Mr. Blum did not personally perform an
    economic analysis of the transaction or consult with his
    investment advisers about the transaction.      He simply inquired
    into KPMG’s reputation.   On the basis of two hour-long meetings
    with Mr. Hasting and without a written prospectus or other
    documentation, Mr. Blum decided to participate in the OPIS
    transaction.
    Mr. Blum, on his own behalf and on behalf of the Blum Trust,
    signed an engagement letter in September 1998 (KPMG engagement
    letter).   Mr. Blum signed the KPMG engagement letter only four
    days before he signed a stock purchase agreement to sell $40
    million of Buy.com shares.   Pursuant to the KPMG engagement
    letter, Mr. Blum and the Blum Trust retained KPMG to provide
    -7-
    advice on the OPIS transaction.    KPMG agreed to provide a tax
    opinion letter to Mr. Blum for the OPIS transaction, but only if
    requested.   Upon such request, the opinion letter would rely on
    “appropriate” facts and representations, and state that the tax
    treatment described in the opinion would “more likely than not”
    be upheld.   KPMG specified, in the KPMG engagement letter, that
    its fees were based on the complexity of its role and the value
    of the services provided, rather than time spent.    KPMG’s minimum
    fee was to be $687,500, with an additional amount to be agreed on
    by the parties.
    Except for a call from Mr. Hasting to Mr. Blum about a month
    into the OPIS transaction, Mr. Blum did not track or monitor the
    transaction.   He was generally unfamiliar with the entities
    involved in his OPIS transaction, other than KPMG and UBS AG
    (UBS), and lacked even a generalized knowledge about the assets
    involved in the deal.
    C. Foreign Special Purpose Entities
    Three foreign entities were formed to implement Mr. Blum’s
    OPIS transaction, although he was not familiar with them.
    Alfaside Limited (Alfaside) was incorporated in the Isle of Mann
    on September 28, 1998.   Four days later, Benzinger GP, Inc.
    (Benzinger GP) was incorporated as a Cayman Islands exempted
    -8-
    company.3   The following day, Alfaside acquired 100-percent
    ownership of Benzinger GP and formed a Cayman Islands limited
    partnership with Benzinger GP called Benzinger Investors, L.P.
    (Benzinger LP).4   Petitioners and KPMG intended that Benzinger GP
    and Benzinger LP would both be corporations for U.S. Federal
    income tax purposes.5   The following diagram illustrates the
    ownership structure of the three foreign entities:
    3
    A Cayman Islands exempted company is a common choice for
    U.S. practitioners creating a foreign entity. An exempted
    company’s operation is conducted mainly outside the Cayman
    Islands. A 20-year exemption from taxation in the Cayman Islands
    is typically applied for.
    4
    Benzinger LP filed a Form SS-4, Application for Employer
    Identification Number. It received a notification of its U.S.
    Federal tax identification number on Dec. 22, 1998.
    5
    Petitioners and KPMG took the position that Benzinger GP
    defaulted to corporate treatment but also filed a protective
    check-the-box election on Form 8832, Entity Classification
    Election, electing corporate treatment. See sec.
    301.7701–3(b)(2), (c)(1)(i), Proced. & Admin. Regs. Benzinger LP
    did not default to corporate treatment, but petitioners and KPMG
    took the position that it was eligible to elect its
    classification and also filed a Form 8832 electing corporate
    treatment for Benzinger LP. See sec. 301.7701–3(a), (b)(2),
    (c)(1)(i), Proced. & Admin. Regs.
    -9-
    D. QA Investments
    A few days later, the Blum Trust retained QA Investments,
    LLC (QA) to serve as its investment adviser for the OPIS
    transaction.6    Mr. Blum was not familiar with QA and had never
    spoken with anyone at QA when his grantor trust retained QA’s
    services.   Nevertheless, the investment advisory agreement (Blum
    Trust advisory agreement) between the Blum Trust and QA gave QA
    substantial discretionary authority with respect to specified
    funds owned by the Blum Trust, subject to the investment
    objectives.     The Blum Trust’s investment objectives specified an
    6
    Quadra Capital Management, L.P., d.b.a. QA Investments, was
    a financial boutique providing asset management, financial
    advice, brokerage activities and tax planning services.
    -10-
    intent to acquire approximately $2,250,000 of UBS common stock
    and the right to instruct QA to purchase or sell put or call
    options on UBS common stock.    The stated investment objectives
    also included an International Swaps and Derivatives Association
    (ISDA) swap agreement with respect to UBS and a privately
    negotiated call option related to the UBS stock price.7    The Blum
    Trust agreed to pay QA a $135,000 fee within 30 days of the
    execution of the Blum Trust advisory agreement.   The Blum Trust
    paid the fee in October 1998.
    Benzinger LP also retained QA to serve as its investment
    adviser regarding the OPIS transaction pursuant to an investment
    advisory agreement (Benzinger LP advisory agreement).     The
    Benzinger LP advisory agreement gave QA certain discretionary
    authority to implement an investment strategy based on certain
    expectations about UBS stock.   The initial account value to be
    invested was $3,015,000 and the strategy contemplated a $45
    million notional account value.8   QA was to hedge the notional
    7
    ISDA is a trade organization of participants in the market
    for over-the-counter derivatives. ISDA has created a
    standardized contract, the ISDA master agreement, which functions
    as an umbrella agreement and governs all swaps between the
    parties to the ISDA master agreement. See generally K3C Inc. v.
    Bank of Am., N.A., 204 Fed. Appx. 455, 459 (5th Cir. 2006).
    8
    In this context, notional account value refers to the total
    value of a leveraged position. The investment strategy was to be
    initiated through the purchase of UBS securities with a $45
    million market value by securing financing or leverage through a
    variety of possible means including borrowing, margin,
    (continued...)
    -11-
    account value by writing in-the-money covered call options or
    purchasing long significantly out-of-the-money put options.9    QA
    billed Benzinger LP $562,500, calculated as a percentage of the
    notional account value, in December 1998.
    E. UBS
    Union Bank of Switzerland merged with Swiss Bank Corporation
    (SBC) in mid-1998, a year at issue, to form the entity now known
    as UBS.   QA first introduced UBS’ Global Equity Derivatives group
    to the OPIS transaction.   KPMG subsequently provided additional
    information about the transaction to UBS.   A UBS officer
    estimated that UBS’ profit for each OPIS transaction would be 2.5
    percent to 3 percent of the notional amount of the transaction.
    The price of UBS stock rose over 48 percent during the
    course of petitioners’ OPIS transaction.
    8
    (...continued)
    derivatives and other investment techniques.
    9
    Options are often referred to as being “at-the-money,” “in-
    the-money,” or “out-of-the-money.” An option that is “at-the-
    money” has its strike price equal to the market price of the
    underlying asset. An option is “in-the-money” when the option’s
    strike price is less than the current market price of the
    underlying asset. If the value of the underlying asset is
    greater than the exercise price for a call option or less than
    the exercise price for a put option, that option is said to be
    “in-the-money.” In this case, it is advantageous to the owner of
    the option to exercise his or her right under the option as
    opposed to acquiring or selling such assets in the stock market.
    An option is “out-of-the-money” when it would be disadvantageous
    to exercise the option, as opposed to acquiring or selling the
    assets in the stock market.
    -12-
    III. The Transaction
    Having introduced the participants, we now delve into the
    operation of petitioners’ OPIS transaction.     We explain the
    different transactions and steps that make up the larger whole.
    A. Step 1: The Blum Trust Purchases UBS Stock and GP Call
    Option; Enters into Equity Swap
    Mr. Blum wired $2,250,000 to the Blum Trust’s Pali Capital
    LLC (Pali) brokerage account (Pali account) on October 2, 1998,
    as contemplated in the Blum Trust advisory agreement.     The same
    day, the Blum Trust used nearly all of those funds to purchase
    10,469 shares of UBS stock.
    Mr. Blum also wired $3,015,000 to SBC as payment from the
    Blum Trust to Alfaside for (1) the first two fixed payments under
    an equity swap agreement (equity swap) and (2) the premium under
    a call option (GP call option).   The equity swap was an agreement
    between the Blum Trust and Alfaside.   Under the equity swap, the
    Blum Trust would pay Alfaside two fixed payments on specified
    payment dates.   After the termination date, Alfaside was to pay
    the Blum Trust an amount in Swiss francs (CHF) to be calculated
    based on the price of UBS common stock as of that date.
    Petitioners and KPMG theorized that the parties were not required
    to withhold U.S. tax under the equity swap.10
    10
    KPMG opined that the equity swap would most appropriately
    be characterized for tax purposes as a notional principal
    contract. If that were the case, payments would be sourced by
    (continued...)
    -13-
    The Blum Trust purchased the GP call option from Alfaside
    for $112,500.        Pursuant to the GP call option, the Blum Trust
    could require Alfaside to either (1) sell its half of the stock
    of Benzinger GP for $229,500 or (2) pay a cash settlement price
    calculated from Benzinger GP’s net asset value.        The Blum Trust
    had a period of less than two months in which it could exercise
    its option.
    B. Step 2:    Benzinger LP Purchases UBS Stock; Constructs
    Collar
    In the second step, Benzinger LP entered into a delayed
    settlement agreement with UBS on October 16, 1998 to purchase
    163,980 shares of UBS stock for $45 million.       Benzinger LP
    treated the transaction for tax purposes as a stock purchase as
    of that date.     It was, however, not required to pay for the stock
    and UBS was not required to deliver the stock until November 27,
    1998.     Benzinger LP’s purported $45 million basis in the 163,980
    shares would allegedly shift to the Blum Trust and therefore to
    petitioners on November 27 under step 3 below.
    Also on October 16, Benzinger LP and UBS used put and call
    options to construct a collar on the 163,980 UBS shares.11
    10
    (...continued)
    the residence of the taxpayer and therefore exempt from
    withholding. See sec. 1441; sec. 1.863-7(b), Income Tax Regs.
    11
    A collar is an option strategy that limits the possible
    positive or negative returns on an underlying investment to a
    specific range. Generally, in an option collar transaction, an
    (continued...)
    -14-
    Benzinger LP purchased 163,980 put options12 from UBS and sold
    147,58213 call options14 to UBS.    Pursuant to their terms, the
    options could be exercised only on their November 27, 1998
    expiration date, and any options that were in-the-money on that
    expiration date would be automatically exercised.
    The call options had a range option feature that required
    UBS to pay Benzinger LP certain amounts if the price of UBS stock
    achieved certain levels on specified days (RECAP feature).     On
    the same day Benzinger LP and UBS entered into the options,
    however, the price of the UBS stock closed below the specified
    level.    The stock’s closing below the specified level eliminated
    or terminated the RECAP feature before any payments came due
    under it.   The share price drop also reset the strike price on
    the call options to 90 percent, the same as the strike price on
    the put options.
    The cost of the UBS call options was almost CHF 3 million
    more than the cost of the Benzinger LP put options.     Benzinger LP
    11
    (...continued)
    investor purchases a put option and sells a call option.
    12
    In industry parlance, these put options are plain-vanilla
    90-percent put options.
    13
    These options represent 90 percent of the total number of
    options.
    14
    In industry parlance and as partially described below,
    these call options could be considered 95-percent call options
    with barrier and reset and embedded range options.
    -15-
    was required to deposit that difference with UBS as part of the
    security for the stock purchase.     The remainder of the security
    posted with UBS consisted of the $3,015,000 that the Blum Trust
    paid for the equity swap and the GP call option, converted into
    CHF.15
    In sum, Benzinger LP purported to purchase $45 million worth
    of UBS stock on October 16, 1998, but paid no money, received no
    stock and entered into transactions that would cause it to never
    receive at least 90 percent of the stock.
    QA subsequently sent UBS a document denominated “trade
    ticket” that ensured Benzinger LP would not receive the other 10
    percent of the stock.     The trade ticket ordered UBS to
    simultaneously redeem any UBS shares held by Benzinger LP on
    November 27, 1998 after the call or put options were exercised.
    C. Step 3: UBS Redeems the 163,980 Shares While the Blum
    Trust Purchases 163,980 Call Options
    In the third step, UBS redeemed the 163,980 shares that
    Benzinger LP had acquired that day pursuant to the delayed
    settlement.     This was primarily completed through automatic
    exercise of the call options, which were in-the-money on November
    27, 1998.16
    15
    CHF 6,880,935 was deposited with UBS, composed of CHF
    2,913,195 net amount from the put and call options and CHF
    3,967,740 (exchanged from $3,015,000).
    16
    The put options were out-of-the money on that date and
    (continued...)
    -16-
    Pursuant to the trade ticket, UBS redeemed the remaining
    16,398 shares that were not included in the call options on the
    same day.     The cumulative result of these transactions was as
    follows:
    Transaction               Information             CHF
    Step 2 transactions         163,980 shares               -4,622,760
    (delayed settlement,
    collar) and UBS
    redemption
    Deposit from the Blum       $3,105,000 converted to       3,967,740
    Trust                       CHF
    Interest on collateral                                           6,984
    Net premium due                                           2,913,195
    Benzinger LP on
    collar
    Total                   Due to Benzinger LP from      2,265,159
    UBS
    The total due from UBS to Benzinger LP, CHF 2,265,159, was
    converted to $1,660,065 and paid on December 8, 1998.
    At the same time that UBS redeemed the 163,980 shares, the
    Blum Trust purportedly purchased 163,980 out-of-the-money call
    options on UBS stock (OTM call options).     The OTM call options
    were 16.5 percent out-of-the-money.     They cost $675,000 and
    expired a month later on December 28, 1998.
    16
    (...continued)
    therefore expired worthless. See supra note 9 for an explanation
    of in-the-money and out-of-the-money options. See infra note 17
    for an explanation of expiring worthless.
    -17-
    D. Step 4: Closing Out
    Mr. Blum then closed out the OPIS transaction.     The Blum
    Trust’s 163,980 call options were left to expire worthless on
    December 28, 1998.17   On the same day, the Blum Trust also sold
    10,469 shares of UBS stock that had been purchased less than
    three months before.     In early January 1999 the Blum Trust
    purportedly received from Alfaside (1) $368,694 for cash settling
    the GP call option and (2) approximately $1.6 million pursuant to
    the equity swap.
    E. The Net Result
    At the conclusion of this convoluted and contrived series of
    transactions, the net cost of the OPIS transaction to Mr. Blum
    was approximately $1.5 million.     For that cost, the OPIS
    transaction yielded over $45 million in capital losses to offset
    capital gains on tax returns petitioners filed.     The following
    diagram depicts the cumulative transaction:
    17
    Options have an exercise period or date(s) and an
    expiration date, and therefore generally lose value as time
    passes. If an option expires out-of-the-money (below the
    exercise price for a call option and above the exercise price for
    a put option), then the option will be said to expire worthless.
    -18-
    IV. Tax Returns
    KPMG prepared petitioners’ tax returns, on which they
    claimed over $45 million in capital losses for 1998 from the OPIS
    transaction.   Mr. Blum reported these losses on the Blum Trust’s
    tax return for 1998, the only tax return the Blum Trust has ever
    filed.   The Blum Trust’s alleged losses were reported in a chart
    that included the following:
    -19-
    Date                  Gross       Cost or
    Item    Acquired    Date        Sales        Other      Gain / Loss
    Sold        Price        Basis
    UBS        10/2/98   12/28/98   $3,257,593   $39,681,91   -$36,424,324
    stock                                                 7
    UBS       11/27/98   12/27/98      -0-        8,629,508     -8,829,509
    options
    Buy.com    7/30/97   10/20/98      500,000      -0-            500,000
    Buy.com    7/30/97   10/29/98   20,000,000      -0-         20,000,000
    Buy.com    7/30/97   10/30/98   20,000,000      -0-         20,000,000
    Buy.com    7/30/97    8/17/98    5,000,000      -0-          5,000,000
    The loss of over $36 million was reported on the Blum Trust’s
    sale of the 10,469 shares of UBS stock purchased at step 1.       The
    nearly $9 million loss was reported on the 163,860 call options
    purchased at step 3, which expired worthless.      The capital gains
    from the sales of Buy.com shares were essentially eliminated by
    the losses claimed from the OPIS transaction.      Petitioners
    reported this net difference, as adjusted by a few other
    unrelated sales, on the income tax return they filed for 1998.
    Petitioners also claimed a $1,754,670 capital loss from the
    equity swap on the income tax return they filed for 1999.
    V. Tax Opinion
    The KPMG engagement letter stated that KPMG would provide a
    tax opinion letter regarding the OPIS transaction, if requested.
    KPMG sent to Mr. Blum a letter, dated after petitioners filed an
    income tax return for 1998, asking Mr. Blum to represent certain
    information about the OPIS transaction.      KPMG agreed to finalize
    and issue its tax opinion after receiving the signed
    -20-
    representation letter.   Mr. Blum signed the representation letter
    in May 1999.   In that letter, Mr. Blum represented that he had
    independently reviewed the economics underlying the investment
    strategy and believed it had a reasonable opportunity to earn a
    reasonable pre-tax profit.    He made this representation even
    though he had not performed an economic analysis of the
    transaction or consulted with his investment advisers about the
    transaction.
    At some point after mid-May 1999 KPMG executed a tax opinion
    letter (tax opinion) dated as of December 31, 1998.    The 99-page
    tax opinion stated that it relied on representations from Mr.
    Blum, Benzinger GP and QA.    KPMG opined that it was more likely
    than not that (1) Benzinger LP and Benzinger GP would be treated
    as corporations for U.S. Federal income tax purposes, (2) the
    amount paid by UBS in redemption of Benzinger LP’s UBS shares
    would be treated as a dividend, (3) Benzinger LP’s tax basis in
    the redeemed UBS shares would be attributed and allocated to the
    Blum Trust’s separately purchased UBS shares and potentially to
    the Blum Trust’s UBS call options, (4) the Blum Trust would not
    be subject to U.S. tax on the dividend received by Benzinger LP
    for redeeming its UBS shares and (5) payments made by the Blum
    Trust to Alfaside under the swap contract would not be subject to
    U.S. withholding tax.    The record does not indicate when or if
    petitioners received the tax opinion.
    -21-
    VI. Aftermath
    KPMG’s tax-focused transactions, including OPIS, soon became
    a topic of governmental and popular interest.
    A. Commissioner’s Position on OPIS
    The Commissioner disagreed with the positions taken in
    KPMG’s “more likely than not” tax opinion and challenged the
    validity of basis-shifting transactions such as OPIS in July
    2001, nearly three years after Mr. Blum entered into the OPIS
    transaction.    The Commissioner rejected the foundations of these
    transactions and noted that reasons for disallowance could
    include (1) the redemption does not result in a dividend, (2) the
    basis shift is improper and (3) there is no stock attribution or
    basis shift because the transaction serves no purpose other than
    tax avoidance.   Notice 2001-45, 2001-2 C.B. 129.
    The next year, the Commissioner issued a settlement
    initiative for basis-shifting tax shelters, such as OPIS.
    Announcement 2002–97, 2002-2 C.B. 757.    The Commissioner
    permitted settling taxpayers to claim 20 percent of the claimed
    losses and waived penalties in certain cases if the settling
    taxpayers conceded 80 percent of the claimed losses.    Id.   Later
    that year, the Commissioner also issued a coordinated issue paper
    presenting in greater detail his rejection of OPIS transactions.
    Industry Specialization Program Coordinated Issue Paper, “Basis
    Shifting” Tax Shelter, 
    2002 WL 32351285
     (Dec. 3, 2002).
    -22-
    B. KPMG’s Indictment
    Around the same time, KPMG’s legal opinions became the focus
    of the United States Senate Permanent Subcommittee on
    Investigations’ (committee) inquiry into the development and
    marketing of abusive tax shelters.     The committee eventually
    focused on four transactions designed and promoted by KPMG, one
    of which was OPIS.
    Facing the possibility of grand jury indictment, KPMG
    entered into a deferred prosecution agreement (DPA) with the
    Government in August 2005.    KPMG agreed to the filing of a
    one-count information charging KPMG with participating in a
    conspiracy to defraud the United States, commit tax evasion and
    make and subscribe false and fraudulent tax returns.     It admitted
    and accepted that it helped high-net-worth individuals evade tax
    by developing, promoting and implementing unregistered and
    fraudulent tax shelters.    It further admitted that KPMG tax
    partners engaged in unlawful and fraudulent conduct, including
    issuing opinions they knew relied on false facts and
    representations.   KPMG agreed to pay the Government $456 million,
    to limit its tax practice to comply with certain guidelines and
    to cooperate with any investigation about which KPMG had
    knowledge or information.
    Later, during 2005, Federal prosecutors obtained numerous
    indictments against current and former KPMG employees and
    -23-
    partners.   The indicted individuals were charged with conspiracy
    and tax evasion for designing, marketing and implementing tax
    shelters, including OPIS.
    C. Blum v. KPMG
    Despite the DPA, KPMG’s legal battles continued.   Mr. Blum
    was one of many clients who sued KPMG in the aftermath of its
    indictment and the related IRS scrutiny.   He filed a complaint
    against KPMG in Los Angeles Superior Court at the end of 2009 in
    connection with the OPIS transaction.
    Mr. Blum refers to OPIS and BLIPS in his lawsuit as the “Tax
    Strategies.”   Mr. Blum alleges in his suit that KPMG breached its
    fiduciary duty to him and induced him to pursue a course of
    action that he would not have otherwise pursed.   In particular,
    Mr. Blum alleges that he was induced to invest millions of
    dollars in the Tax Strategies and to conduct his business to
    realize taxable income that would be offset by the losses the Tax
    Strategies generated.   He further claims that, in reliance on
    KPMG, he did not adopt other strategies to defer or minimize tax
    liability or make different decisions regarding share sales.     He
    seeks damages of over $100 million.
    VII. Deficiency
    As previously mentioned, respondent determined deficiencies
    in, and penalties regarding, petitioners’ Federal income taxes
    for the years at issue.   Petitioners timely filed a petition with
    -24-
    this Court for redetermination of the positions respondent set
    forth in the deficiency notice.    As previously mentioned, the
    parties resolved certain issues in their stipulation of settled
    issues and the Court dismissed those portions of the deficiencies
    and penalties pertaining to petitioners’ BLIPS transaction.
    OPINION
    The subject transaction presents a case of first impression
    in this Court.   We are asked to decide whether petitioners are
    entitled to deduct losses from their OPIS transaction.    We must
    also decide whether petitioners are liable for any accuracy-
    related penalties for underpayments resulting from the OPIS
    transaction.   We begin with the parties’ arguments regarding this
    complicated OPIS transaction.
    Petitioners argue that their claimed benefits from the OPIS
    transaction were taken according to the letter of the tax laws.
    In support of that position, petitioners argue that OPIS yielded
    the claimed losses pursuant to the following analysis:
    (1) UBS’ exercise of the call options and Benzinger LP’s
    sale of the remaining shares to UBS was a redemption of stock
    under section 317(b).
    (2) To determine whether a redemption qualifies as a sale or
    exchange or as a distribution, the stock attribution rules apply.
    Secs. 302(c), 318(a).   Petitioners argue that, under the stock
    attribution rules, the Blum Trust was treated as owning the
    -25-
    163,980 shares that are the subject of its call options, in
    addition to the 10,469 shares that it directly held.    See sec.
    318(a)(4).    Also under these rules, the Blum Trust was treated as
    owning 50 percent of Benzinger GP, and therefore Benzinger LP was
    treated as owning the 10,469 shares directly held by the Blum
    Trust and the 163,980 shares constructively owned by the Blum
    Trust.   See sec. 318(a)(3)(C), (4), (5)(A).
    (3) Because of Benzinger LP’s constructive ownership of the
    Blum Trust’s UBS shares (both direct and constructive), the UBS
    redemption of Benzinger LP’s shares did not completely terminate
    Benzinger LP’s interest in the corporation.    See sec. 302(b)(3).
    Moreover, petitioners argue that it was not a substantially
    disproportionate redemption because Benzinger LP was deemed to
    own the same number of shares before and after step 3 of the
    transaction under the attribution rules.    See sec. 302(b)(2).
    Petitioners theorize that the UBS redemption is essentially
    equivalent to a dividend.    See United States v. Davis, 
    397 U.S. 301
     (1970).    Accordingly, petitioners conclude that the
    redemption would not be treated as a sale or exchange but would
    instead be treated as a distribution of property.    See sec.
    302(a), (d).
    (4) UBS had sufficient earnings and profits in 1998, so the
    distribution pursuant to the UBS redemption would be treated as a
    -26-
    dividend and would not reduce Benzinger LP’s tax basis in the
    redeemed UBS shares.    See sec. 301(c)(1).
    (5) Benzinger LP thus retained its tax basis in the UBS
    shares but did not own any shares directly.   Petitioners took the
    position and argue that Benzinger LP’s basis in the UBS shares
    therefore could be allocated to the Blum Trust’s UBS shares and
    options because the attribution of shares from the Blum Trust
    caused the redemption to be treated as a dividend.   See Levin v.
    Commissioner, 
    385 F.2d 521
     (2d Cir. 1967), affg. 
    47 T.C. 258
    (1966); sec. 1.302-2(c) and Example (2), Income Tax Regs.18
    Petitioners further posit that the OPIS transaction has
    economic substance because Mr. Blum entered into it for
    investment purposes and had a reasonable possibility of profiting
    from the transaction.    They also urge the Court that they
    reasonably relied on their long-time tax adviser, so they should
    not be liable for penalties in case of deficiencies.
    Respondent argues petitioners are not entitled to deduct
    losses from the OPIS transaction because they incorrectly
    reported their Federal income tax treatment of certain steps.
    Specifically, respondent alleges that petitioners’ tax treatment
    18
    Petitioners took the position that UBS’ redemption of
    Benzinger LP’s shares was not taxable to the Blum Trust because
    (a) the equity swap did not, in substance, transfer to the Blum
    Trust an equity interest in Benzinger LP and (b) the GP call
    option did not implicate the controlled foreign corporation,
    foreign personal holding company and passive foreign investment
    company provisions of the Code.
    -27-
    of the OPIS transaction is incorrect because Benzinger LP never
    owned the 163,980 UBS shares for Federal income tax purposes and
    therefore did not have a $45 million basis that could be shifted.
    Respondent also takes the position that Benzinger LP could not
    shift its alleged basis to the Blum Trust because UBS’ redemption
    of Benzinger LP’s UBS stock was a distribution in a sale or
    exchange of that stock, and not a dividend.   Respondent further
    argues that petitioners’ losses are disallowed because the
    transaction lacks economic substance.19
    We agree with respondent that the OPIS transaction lacked
    economic substance.   We admit KPMG painstakingly structured an
    elaborate transaction with extensive citations to complex Federal
    tax provisions.   The entire series of steps, however, was a
    subterfuge to orchestrate a capital loss.   A taxpayer may not
    deduct losses resulting from a transaction that lacks economic
    substance, even if that transaction complies with the literal
    terms of the Code.    See Coltec Indus., Inc. v. United States, 
    454 F.3d 1340
    , 1352–1355 (Fed. Cir. 2006); Keeler v. Commissioner,
    
    243 F.3d 1212
    , 1217 (10th Cir. 2001), affg. Leema Enters., Inc.
    v. Commissioner, T.C. Memo. 1999-18.   Accordingly, we do not
    address the parties’ arguments regarding the merits of
    19
    Respondent also argues that petitioners’ losses are
    disallowed under sec. 165 because they were not incurred in a
    transaction entered into for profit and that they are limited by
    the at-risk rules in sec. 465. We need not reach these arguments
    because of our other holdings.
    -28-
    petitioners’ treatment of each step within the OPIS transaction.
    Instead, we begin our analysis with the general principles of the
    economic substance doctrine.20
    I. Merits of OPIS Under the Economic Substance Doctrine
    A court may disregard a transaction for Federal income tax
    purposes under the economic substance doctrine if it finds that
    the taxpayer failed to enter into the transaction for a valid
    business purpose but rather sought to claim tax benefits not
    contemplated by a reasonable application of the language and
    purpose of the Code or its regulations.21 See, e.g., New Phoenix
    Sunrise Corp. & Subs. v. Commissioner, 
    132 T.C. 161
     (2009), affd.
    408 Fed. Appx. 908 (6th Cir. 2010); Palm Canyon X Invs., LLC v.
    Commissioner, T.C. Memo. 2009-288.      There is, however, a split
    among the Courts of Appeals as to the application of the economic
    20
    The taxpayer generally bears the burden of proving the
    Commissioner’s determinations are erroneous. Rule 142(a). The
    burden of proof may shift to the Commissioner if the taxpayer
    satisfies certain conditions. Sec. 7491(a). Our resolution is
    based on a preponderance of the evidence, not on an allocation of
    the burden of proof. Therefore, we need not consider whether
    sec. 7491(a) would apply. See Estate of Bongard v. Commissioner,
    
    124 T.C. 95
    , 111 (2005).
    21
    Congress codified the economic substance doctrine mostly
    as articulated by the Court of Appeals for the Third Circuit in
    ACM Pship. v. Commissioner, 
    157 F.3d 231
    , 247–248 (3d Cir. 1998),
    affg. in part and revg. in part on an issue not relevant here
    T.C. Memo. 1997–115. See sec. 7701(o), as added to the Code by
    the Health Care and Education Reconciliation Act of 2010, Pub. L.
    111–152, sec. 1409, 124 Stat. 1067; see also H. Rept. 111–443(I),
    at 291–299 (2010). The codified doctrine does not apply here
    pursuant to its effective date.
    -29-
    substance doctrine.   An appeal in this case would lie to the
    Court of Appeals for the Tenth Circuit absent stipulation to the
    contrary and, accordingly, we follow the law of that circuit.
    See Golsen v. Commissioner, 
    54 T.C. 742
     (1970), affd. 
    445 F.2d 985
     (10th Cir. 1971).
    The Court of Appeals for the Tenth Circuit applies a so-
    called unitary analysis in which it considers both the taxpayer’s
    subjective business motivation and the objective economic
    substance of the transactions.    See Sala v. United States, 
    613 F.3d 1249
     (10th Cir. 2010); Jackson v. Commissioner, 
    966 F.2d 598
    , 601 (10th Cir. 1992), affg. T.C. Memo. 1991-250.    The
    presence of some profit potential does not necessitate a finding
    that the transaction has economic substance.     Keeler v.
    Commissioner, supra at 1219.     Instead, that Court of Appeals
    requires that tax advantages be linked to actual losses.     See
    Sala v. United States, supra at 1253; Keeler v. Commissioner,
    supra at 1218-1219.   It has further reasoned that “correlation of
    losses to tax needs coupled with a general indifference to, or
    absence of, economic profits may reflect a lack of economic
    substance.”   Keeler v. Commissioner, supra at 1218.    Applying
    those standards, we hold that petitioners’ OPIS transaction lacks
    economic substance and we now discuss our underlying reasoning
    and conclusions for our holding.
    -30-
    A. Prearranged Steps Designed To Generate Loss
    Petitioners’ OPIS transaction was a structured deal with
    several components, some straight-forward and some complex.     The
    components of this deal were carefully pieced together to
    generate, preserve and shift a substantial tax basis so as to
    obviate petitioners’ $45 million capital gain.   We conclude,
    based on the record and the entirety of the transactions, that
    petitioners’ OPIS transaction was designed to create a tax loss
    that would offset their capital gains from sales of Buy.com
    shares.
    KPMG designed OPIS’ prearranged steps to generate a
    significant, artificial loss.   KPMG sought clients with
    substantial capital gains for the OPIS transaction.   Investors
    were targeted based on their potential capital gains and not
    their investment profiles.   Indeed, KPMG had a minimum capital
    gains requirement for clients participating in the transaction.
    Mr. Blum contends that he had no interest in a tax shelter
    when he met with Mr. Hasting.   The record conflicts, however,
    with his contention.   Mr. Law suggested that Mr. Blum contact
    KPMG’s capital transaction group because he knew that Mr. Blum
    had potential capital gains from stock sales.    Mr. Blum retained
    KPMG for the OPIS transaction just days before selling $40
    million of Buy.com shares.   Mr. Blum retained KPMG as his tax
    adviser, not as his investment adviser.
    -31-
    KPMG intended OPIS as a loss-generating transaction.     The
    OPIS transaction was a prearranged set of steps that, from the
    outset, was designed and intended to generate a loss.    Those
    circumstances are indicative of transactions lacking economic
    substance.   See Sala v. United States, supra at 1253.
    B. Mr. Blum Did Not Approach the Transaction as an Investor
    Mr. Blum contends that he did not view the prearranged OPIS
    steps as a loss-generating transaction, but that he intended to
    make a potentially high-yielding investment.   Petitioners’
    reliance on this subjective prong of the economic substance
    analysis is not supported by the facts.   We do not accept Mr.
    Blum’s claim that he subjectively believed the OPIS transaction
    would be profitable because his actions during or after the
    transaction conflict with his contention.
    Mr. Blum’s contention concerning his intent on entering into
    the transaction conflicts, for example, with the KPMG engagement
    letter for tax consultation services that provides for a tax
    opinion about losses from the transaction.   Mr. Blum’s asserted
    focus on investment does not comport with his retention of QA as
    an investment adviser when he knew little about and never spoke
    to anyone at QA.   He hired an investment adviser that he did not
    know and he did so through a tax adviser, which suggests that
    tax, not investment, was the primary consideration.
    -32-
    Mr. Blum testified that $5 million was a relatively sizable
    amount of money to him.    The record indicates that Mr. Blum
    essentially entrusted this sizable amount of money to an unknown
    investment adviser based on two hour-long presentations from his
    tax adviser.   Mr. Blum did not perform an economic analysis of
    the OPIS transaction, nor did he ask his existing investment
    advisers to review it.    He had no general knowledge of the
    participants (except for KPMG and UBS) and no understanding of
    the transaction.   Furthermore, Mr. Blum did not track his
    investment, except to the extent that he received a call from
    KPMG a month into the deal.
    Mr. Blum’s actions belie his testimony.    His lack of due
    diligence in researching the OPIS transaction indicates that he
    knew he was purchasing a tax loss rather than entering into a
    legitimate investment.    See Pasternak v. Commissioner, 
    990 F.2d 893
    , 901 (6th Cir. 1993), affg. Donahue v. Commissioner, T.C.
    Memo. 1991-181; Country Pine Fin., LLC v. Commissioner, T.C.
    Memo. 2009-251.
    Mr. Blum’s statements in his subsequent suit against KPMG
    confirm his lack of subjective profit motive.    In his suit, Mr.
    Blum alleges that he was induced to invest millions of dollars in
    a tax strategy and to conduct his business so as to realize
    taxable income that would be offset by losses generated by OPIS.
    He further claims that, in reliance on KPMG, he did not adopt
    -33-
    other strategies to defer or minimize his tax liability or make
    different decisions regarding share sales.    Mr. Blum’s actions
    during and after the OPIS transaction do not indicate a profit
    motive.
    C. Loss Had No Economic Reality
    Petitioners’ significant capital losses from the OPIS
    transaction were not only intentional, but they were also
    artificial.   Indeed, the claimed losses created by the OPIS
    transaction were prearranged and intended to be artificial.     Mr.
    Blum invested approximately $6 million into the OPIS transaction
    and lost approximately $1.5 million, yet the transaction
    generated over $45 million in capital losses.    Petitioners’
    disproportionate losses violated the principle that tax
    advantages must be linked to actual losses.    See Keeler v.
    Commissioner, 243 F.3d at 1218.
    Benzinger LP was able to create an artificial basis in UBS
    shares, which it otherwise would not have, through Benzinger LP’s
    delayed settlement stock purchase of UBS shares and the collar on
    those shares.   Benzinger LP treated the UBS share redemption as a
    dividend through its application of the attribution rules and the
    rules governing redemptions.   This treatment had no tax
    consequences to Benzinger LP, but allowed it to retain its
    alleged basis in the shares for Federal income tax purposes.
    Retaining this $45 million basis was crucial.    As Benzinger LP no
    -34-
    longer held any interests in UBS shares, its basis allegedly
    transferred to petitioners’ UBS shares and options.   Petitioners
    therefore claimed a substantial capital loss upon selling their
    UBS shares and expiration of their options.
    Petitioners’ claimed capital losses far exceeded their
    investments in the shares and options.   Petitioners’ claimed loss
    on their sale of directly-held UBS shares acquired in step 1 of
    the transaction is particularly significant to the planned tax
    strategy.   In reality, the UBS shares appreciated substantially
    during this period.   Petitioners’ earned approximately $1 million
    (before fees) on their direct investment in UBS shares, yet they
    claimed a capital loss of over $36 million on the sale.
    In other words, petitioners claimed a substantial capital
    loss because they received a tax-exempt foreign entity’s
    carefully constructed and carefully retained basis in shares that
    it never actually received.   Petitioners incurred no such
    economic loss of the stated magnitude.   Indeed, petitioners do
    not contest that their loss is fictional.   The absence of
    economic reality is the hallmark of a transaction lacking
    economic substance.   Sala v. United States, 613 F.3d at 1254; see
    also Coltec Indus., Inc. v. United States, 454 F.3d at 1352;
    Keeler v. Commissioner, supra at 1218–1219; K2 Trading Ventures,
    LLC v. United States, ___ Fed. Cl. ___, 
    2011 WL 5998957
     (Nov. 30,
    2011).
    -35-
    D. Loss Dwarfs Profit Potential
    Petitioners’ artificial $45 million loss has no meaningful
    relevance to the minuscule potential for profit from OPIS.
    Petitioners’ expert, Dr. James Hodder (Dr. Hodder), concluded
    that petitioners had a 76.3-percent chance of losing money.
    Despite the high risk, Dr. Hodder concluded that OPIS had
    potential for high yields that could make the deal an appropriate
    investment for the right investor.      Dr. Hodder calculated that
    OPIS had a 19.1-percent chance of realizing a $600,000 profit.
    He further concluded that petitioners had a 7.6-percent chance of
    realizing a $3 million profit.    These amounts are de minimis when
    compared to petitioners’ capital losses of over $45 million from
    OPIS.   The expected tax benefit dwarfs any potential gain such
    that the economic realities of OPIS are meaningless in relation
    to the tax benefits.   See Sala v. United States, supra at 1254;
    Rogers v. United States, 
    281 F.3d 1108
    , 1116 (10th Cir. 2002).
    The mere presence of a profit potential does not automatically
    impute substance where a common-sense examination of the
    transaction and the record in toto reflects a lack of economic
    substance.   Sala v. United States, supra at 1254; Keeler v.
    Commissioner, supra at 1219.
    E. The Numbers Do Not Add Up
    Despite the presence of some profit potential in OPIS, we
    find that profit was not a primary purpose of the transaction.
    -36-
    The expert testimony presented in this case, while not central to
    our determination, loosely supports the notion that OPIS was
    intended to generate a loss.
    Petitioners and respondent both provided the Court with
    expert reports that sought to quantify the profitability of
    petitioners’ OPIS transaction.    Petitioners’ expert, Dr. Hodder,
    performed simulations to calculate the expected probability that
    the Blum Trust would realize a profit when it entered into the
    OPIS transactions.    Dr. Hodder concluded that the deal had a
    23.7-percent chance of breaking even before taxes, a 19.1-percent
    chance of realizing a 10-percent return ($600,000 profit) and a
    7.6-percent chance of realizing a 50-percent return ($3 million
    profit).   The greatest chance for profit was in the Blum Trust’s
    direct investment in UBS shares, which was more than twice as
    likely as the GP call option and the equity swap to yield a
    profit.    Dr. Hodder concluded that the OTM call options were the
    least likely to yield a profit, with a mere 11.3-percent chance
    of breaking even.
    Dr. Hodder focused on the high volatility in UBS stock
    prices at the time.    Based on his volatility estimates, Dr.
    Hodder ultimately concluded that OPIS presented a high-risk
    opportunity that had potential for high rewards.    He stated that
    “[i]t is kind of a long shot gamble, but it is a long shot gamble
    -37-
    with a huge upside, and I don’t think that is unreasonable, but
    it is not something that I would have done.”
    Dr. Hodder’s calculations are helpful, but his conclusion
    that there is some profit potential does not require us to find
    that the transaction has economic substance.    See Keeler v.
    Commissioner, 243 F.3d at 1219; see also K2 Trading Ventures, LLC
    v. United States, ___ Fed. Cl. at ___, 
    2011 WL 5998957
     at *19
    (“potential for profit does not in and of itself establish
    economic substance--especially where the profit potential is
    dwarfed by tax benefits”).   His calculations assume a transaction
    that was not pre-ordained to create a loss intended specifically
    to offset a particular gain.
    Respondent’s expert witness, Dr. A. Lawrence Kolbe (Dr.
    Kolbe), did not address the question of whether petitioners’ OPIS
    transaction had profit potential.     Instead, Dr. Kolbe looked at
    the net present value and the expected rate of return relative to
    the cost of capital.   He concluded that the OPIS transaction, as
    a whole, was extremely unprofitable.    Dr. Kolbe determined that
    petitioners’ entry into OPIS resulted in an immediate loss of 36
    percent of the invested amount because the securities were priced
    far above their value.
    A bad deal or a mispriced asset need not tarnish a
    legitimate deal’s economic substance.    A finding of grossly
    mispriced assets or negative cashflow can, however, contribute to
    -38-
    the overall picture of an economic sham.    See, e.g., Country Pine
    Fin., LLC v. Commissioner, T.C. Memo. 2009-251.
    We note that both experts agreed that the equity swap and
    the OTM call options were highly overpriced, and neither was able
    to replicate the final payment from the GP call option based on
    the record.     We also note that the price of UBS stock rose over
    48 percent during the course of petitioners’ OPIS transaction,
    yet petitioners lost hundreds of thousands of dollars from the
    transaction (without even considering fees) and then claimed
    millions and millions in losses.    The numbers do not add up.
    In sum, the OPIS transaction lacked economic substance.     It
    was intended to create a significant capital loss and worked
    exactly as intended.    Accordingly, the OPIS transaction is
    disregarded for tax purposes and petitioners’ claimed losses are
    disallowed.22
    22
    Respondent alleges that petitioners failed to report
    $35,311 of income in 1999 in connection with the settlement of
    the GP call option. Petitioners claim they were entitled to
    allocate $35,311 of fees paid to KPMG and QA to the basis of the
    GP call option and to recover those amounts when the Blum Trust
    settled the GP call option. Because we find that the OPIS
    transaction lacked economic substance and related losses are
    disallowed without regard to the value or basis of the assets,
    this issue is now moot. See Leema Enters., Inc. v. Commissioner,
    T.C. Memo. 1999–18, affd. sub nom. Keeler v. Commissioner, 
    243 F.3d 1212
     (10th Cir. 2001).
    -39-
    II. Accuracy-Related Penalties
    We now turn to respondent’s determination that petitioners
    are liable for accuracy-related penalties.    A taxpayer may be
    liable for a 20-percent accuracy-related penalty on the portion
    of an underpayment of income tax attributable to, among other
    things, negligence or disregard of rules or regulations.    Sec.
    6662(a) and (b)(1).    The penalty increases to a 40–percent rate
    to the extent that the underpayment is attributable to a gross
    valuation misstatement.   Sec. 6662(h)(1).   An accuracy-related
    penalty under section 6662 does not apply to any portion of an
    underpayment of tax for which a taxpayer had reasonable cause and
    acted in good faith.   Sec. 6664(c)(1).
    Respondent determined that the 40-percent accuracy-related
    penalty applies to petitioners’ underpayment resulting from the
    disallowed losses reported for 1998.    Respondent determined that
    a 20–percent accuracy-related penalty applies on account of a
    disallowed loss and omitted income for 1999.    Petitioners deny
    that they were negligent with respect to 1999 and assert that
    they meet the reasonable cause exception to the accuracy-related
    penalties.
    A. Gross Valuation Misstatement
    Respondent determined an accuracy-related penalty of 40
    percent for a gross valuation misstatement with respect to losses
    reported from the OPIS transaction for 1998.    A taxpayer may be
    -40-
    liable for a 40–percent penalty on that portion of an
    underpayment of tax that is attributable to one or more gross
    valuation misstatements.   Sec. 6662(h).    A gross valuation
    misstatement exists if the value or adjusted basis of any
    property claimed on a tax return is 400 percent or more of the
    amount determined to be the correct amount of such value or
    adjusted basis.   Sec. 6662(h)(2)(A)(i).    The value or adjusted
    basis of any property claimed on a tax return that is determined
    to have a correct value or adjusted basis of zero is considered
    to be 400 percent or more of the correct amount.     Sec.
    1.6662–5(g), Income Tax Regs.
    Our holding that the OPIS transaction lacks economic
    substance results in the total disallowance of the losses at
    issue without regard to the value or basis of the property used
    in the OPIS transaction.   See Leema Enters., Inc. v.
    Commissioner, T.C. Memo. 1999-18.      We have held that the gross
    valuation penalty applies when an underpayment stems from
    deductions or credits that are disallowed because of lack of
    economic substance.   See Petaluma FX Partners, LLC v.
    Commissioner, 
    131 T.C. 84
    , 104-105 (2008), affd. in pertinent
    part, revd. in part and remanded 
    591 F.3d 649
     (D.C. Cir. 2010).
    In the absence of a decision of the Court of Appeals for the
    Tenth Circuit squarely on point, we follow our precedent.
    Consequently, a gross valuation misstatement accuracy-related
    -41-
    penalty applies to petitioners’ underpayment for 1998 absent a
    showing of reasonable cause or some other defense.
    B. Negligence
    Respondent also determined that petitioners are liable for
    the 20-percent accuracy-related penalty because the 1999
    underpayment resulting from a disallowed loss and omitted income
    was due to negligence.   Sec. 6662(a) and (b)(1).   Negligence is
    defined as a “lack of due care or the failure to do what a
    reasonable and ordinarily prudent person would do under the
    circumstances.”   Viralam v. Commissioner, 
    136 T.C. 151
    , 173
    (2011).   Negligence is strongly indicated where “[a] taxpayer
    fails to make a reasonable attempt to ascertain the correctness
    of a deduction, credit or exclusion on a return which would seem
    to a reasonable and prudent person to be ‘too good to be true’
    under the circumstances.”   Sec. 1.6662–3(b)(1)(ii), Income Tax
    Regs.   The deficiency determined by respondent with respect to
    petitioners’ tax return for 1999 is linked to OPIS, a “too good
    to be true” transaction.
    An underpayment is not attributable to negligence, however,
    to the extent that the taxpayer shows that the underpayment is
    due to the taxpayer’s reasonable cause and good faith.    See secs.
    1.6662–3(a), 1.6664–4(a), Income Tax Regs.    The burden is upon
    the taxpayer to prove reasonable cause.   See Higbee v.
    Commissioner, 
    116 T.C. 438
    , 447-449 (2001).    We determine whether
    -42-
    a taxpayer acted with reasonable cause and in good faith by
    considering the pertinent facts and circumstances, including the
    taxpayer’s efforts to assess his or her proper tax liability, the
    taxpayer’s knowledge and experience and the reliance on the
    advice of a professional.    Sec. 1.6664-4(b)(1), Income Tax Regs.
    Generally, the most important factor is the extent of the
    taxpayer’s effort to assess the proper tax liability.      Id.
    C. Reasonable Cause and Good Faith
    Petitioners seek to defend against both accuracy-related
    penalties by asserting that they relied on KPMG to prepare the
    tax returns and to assure them that the deductions from the OPIS
    transaction were claimed legally.      The good-faith reliance on the
    advice of an independent, competent professional as to the tax
    treatment of an item may negate an accuracy-related penalty.     See
    sec. 1.6664–4(b), Income Tax Regs.     A taxpayer may rely on the
    advice of any tax adviser, lawyer or accountant.      United States
    v. Boyle, 
    469 U.S. 241
    , 251 (1985); Canal Corp. & Subs. v.
    Commissioner, 
    135 T.C. 199
    , 218 (2010).
    We look to the facts and circumstances of the case and the
    law that applies to those facts and circumstances to determine
    whether a taxpayer reasonably relied on advice.     See sec.
    1.6664–4(c)(1)(i), Income Tax Regs.     We have used a three-prong
    test to guide that review.   Namely, the taxpayer must prove by a
    preponderance of the evidence that (1) the adviser was a
    -43-
    competent professional who had sufficient expertise to justify
    reliance, (2) the taxpayer provided necessary and accurate
    information to the adviser and (3) the taxpayer actually relied
    in good faith on the adviser’s judgment.    106 Ltd. v.
    Commissioner, 
    136 T.C. 67
    , 77 (2011); Neonatology Associates,
    P.A. v. Commissioner, 
    115 T.C. 43
    , 99 (2000), affd. 
    299 F.3d 221
    (3d Cir. 2002).    We review petitioners’ situation in light of
    these factors.
    First, KPMG was a well-known international “Big Four”
    accounting firm.    It had not yet faced the legal and public
    scrutiny that ultimately resulted from its structured tax
    activities.   Mr. Law, who had prepared petitioners’ tax returns
    and helped them through the audits of four tax years, referred
    Mr. Blum to Mr. Hasting.    Accordingly, KPMG and its principals
    had sufficient relevant expertise and properly appeared competent
    to petitioners.
    Petitioners failed, however, to satisfy the second factor.
    Initially, we observe that petitioners provided KPMG and its
    principals with all the relevant financial data needed to assess
    the correct level of income tax.    See sec. 1.6664–4(c)(1)(i),
    Income Tax Regs.    Accordingly, KPMG had the necessary and
    accurate information.    Nevertheless, petitioners failed to
    satisfy the second factor because KPMG’s opinion relied upon
    false representations from Mr. Blum.
    -44-
    The most crucial of these representations was that Mr. Blum
    independently reviewed the economics underlying the investment
    strategy and believed it had a reasonable opportunity to earn a
    reasonable pretax profit.    Mr. Blum knew this representation was
    false, or would have known it if he had read it.     The record, as
    a whole, reflects that the OPIS transaction was structured to
    fabricate a loss.    This loss creation was KPMG’s reason for
    seeking out Mr. Blum and Mr. Blum’s reason for engaging in the
    transaction.   Mr. Blum’s representations to KPMG are contrary to
    this fact and are part of the guise that was used to fabricate
    the intended loss.    Petitioners thus failed to satisfy the second
    factor because Mr. Blum made false representations to KPMG.
    KPMG’s promotion and facilitation of OPIS concerns the last
    factor and the heart of the issue.      Petitioners certainly relied
    on KPMG, and KPMG’s failures toward its client during and after
    the years at issue are well-documented.     Nevertheless, we do not
    find that petitioners actually relied on KPMG in good faith for
    purposes of the reasonable cause and good faith defense to
    accuracy-related penalties.
    Petitioners point to KPMG’s 99-page tax opinion on the OPIS
    transaction, but petitioners did not actually rely on this
    opinion.   The record does not show when the opinion was
    finalized, but we know that it was finalized after petitioners
    filed the tax return for 1998.    As previously mentioned, KPMG’s
    -45-
    opinion also relied upon false representations from Mr. Blum.
    The opinion on which petitioners allegedly relied was thus
    belated and based on a false representation.
    Petitioners also argue that they received oral advice from
    KPMG regarding OPIS.     KPMG did not, however, describe the tax
    opinion to Mr. Blum when he was entering into the transaction.23
    Mr. Blum also did not recount any oral advice that would have
    supported his argument of reasonable reliance.    Petitioners have
    failed to satisfy their burden of showing that they reasonably
    relied on oral advice.
    Finally, we hold that petitioners could not have reasonably
    relied on KPMG because of its role as a promoter.    Reliance is
    unreasonable if the adviser is a promoter of the transaction or
    suffers from an inherent conflict of interest of which the
    taxpayer knew or should have known.     Neonatology Associates, P.A.
    v. Commissioner, supra at 98.     We have held that, when the
    transaction involved is the same tax shelter offered to numerous
    parties, we adopt the following definition of promoter:     “‘an
    adviser who participated in structuring the transaction or is
    23
    The engagement letter also did not provide a description
    of the opinion letter that would be provided upon request. The
    engagement letter stated that the opinion letter would rely on
    “appropriate” facts and representations and would provide that
    the tax treatment described in the opinion would “more likely
    than not” be upheld. It provided no details regarding the tax
    treatment to be described in the opinion or the facts and
    representations that would be required before the opinion could
    be issued.
    -46-
    otherwise related to, has an interest in, or profits from the
    transaction.’”   106 Ltd. v. Commissioner, supra at 79-80 (quoting
    Tigers Eye Trading, LLC v. Commissioner, T.C. Memo. 2009–121).
    KPMG sought clients with significant capital gains and structured
    the OPIS deal for petitioners and numerous other clients.     KPMG
    was a promoter of OPIS and its obvious conflict makes
    petitioners’ reliance unreasonable.
    Petitioners claimed an artificial loss of over $45 million.
    This is exactly the type of “too good to be true” transaction
    that should cause a savvy, experienced businessman to seek
    independent advice.   See Neonatology Associates, P.A. v.
    Commissioner, 299 F.3d at 234 (“When, as here, a taxpayer is
    presented with what would appear to be a fabulous opportunity to
    avoid tax obligations, he should recognize that he proceeds at
    his own peril.”); New Phoenix Sunrise Corp. & Subs. v.
    Commissioner, 132 T.C. at 195.    Petitioners’ decision to rely
    exclusively on KPMG in structuring, facilitating and reporting
    their OPIS transaction was therefore not reasonable.     Petitioners
    did not take their position in good faith and thus lacked
    reasonable cause for that position.     Accordingly, we sustain
    respondent’s determination that petitioners are liable for
    accuracy-related penalties for 1998 and 1999.
    -47-
    We have considered all remaining arguments the parties made
    and, to the extent not addressed, we find them to be irrelevant,
    moot, or meritless.
    To reflect the foregoing and due to the parties’
    concessions,
    Decision will be entered
    under Rule 155.