David F. Hewitt v. Commissioner of IRS ( 2021 )


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  • USCA11 Case: 20-13700     Date Filed: 12/29/2021       Page: 1 of 36
    [PUBLISH]
    In the
    United States Court of Appeals
    For the Eleventh Circuit
    ____________________
    No. 20-13700
    ____________________
    DAVID F. HEWITT,
    TAMMY K. HEWITT,
    Petitioners-Appellants,
    versus
    COMMISSIONER OF IRS,
    Respondent-Appellee.
    ____________________
    Petition for Review of a Decision of the
    U.S. Tax Court
    Agency No. 23809-17
    ____________________
    USCA11 Case: 20-13700        Date Filed: 12/29/2021     Page: 2 of 36
    2                       Opinion of the Court                20-13700
    Before WILSON, LAGOA, Circuit Judges, and MARTINEZ, District
    Judge.
    LAGOA, Circuit Judge:
    David and Tammy Hewitt seek review of the Tax Court’s
    order determining that they were not entitled to carryover a char-
    itable contribution deduction for the donation of a conservation
    easement (the “Easement”). The Tax Court concluded that the
    Easement did not satisfy the “protected-in-perpetuity” require-
    ment, see I.R.C. § 170(h)(5), because the Easement deed violated
    the judicial extinguishment proceeds formula set forth in 
    Treas. Reg. § 1
    .170A-14(g)(6)(ii). Specifically, in the event of judicial ex-
    tinguishment, the Easement deed subtracts the value of post-dona-
    tion improvements to the property from the extinguishment pro-
    ceeds before determining the donee’s share of the proceeds, which
    the Commissioner asserts violated § 1.170A-14(g)(6)(ii) and, thus,
    § 170(h)(5)’s protected-in-perpetuity requirement.
    On appeal, the Hewitts make several arguments as to why
    the Tax Court erred. They contend that the Commissioner’s inter-
    pretation of § 1.170A-14(g)(6)(ii) is incorrect, as subtraction of the
    value of post-donation improvements from the proceeds allocated
    to the donee is the “better reading” of the regulation. As to this
    interpretation argument, we recently determined, in TOT Prop-
    erty Holdings, LLC v. Commissioner, that § 1.170A-14(g)(6)(ii)
    “does not indicate that any amount, including that attributable to
    improvements, may be subtracted out.” 
    1 F.4th 1354
    , 1363 (11th
    USCA11 Case: 20-13700           Date Filed: 12/29/2021       Page: 3 of 36
    20-13700                  Opinion of the Court                             3
    Cir. 2021) (quoting PBBM-Rose Hill, Ltd. v. Comm’r, 
    900 F.3d 193
    ,
    208 (5th Cir. 2018)).
    But, based on the taxpayers’ concession in TOT, 
    id.
     at 1362
    & n.13, we did not address whether § 1.170A-14(g)(6)(ii) was pro-
    cedurally valid under the Administrative Procedures Act (“APA”)
    or substantively valid under the framework in Chevron, U.S.A.,
    Inc. v. Nat. Res. Def. Council, Inc., 
    467 U.S. 837
     (1984). Unlike the
    taxpayers in TOT, the Hewitts challenge the regulation’s validity
    on appeal. Specifically, the Hewitts argue that the Commissioner’s
    interpretation of § 1.170A-14(g)(6)(ii)—prohibiting the subtraction
    of the value of post-donation improvements to the property on
    which a conservation easement exists from the proceeds in the
    event of judicial extinguishment—is arbitrary and capricious for vi-
    olating the procedural requirements of the APA, see 
    5 U.S.C. § 706
    ,
    because the U.S. Treasury Department failed to respond to signifi-
    cant comments as to the improvements issue in promulgating the
    regulation. The Hewitts further argue that the regulation is sub-
    stantively invalid under Chevron as an unreasonable interpretation
    of the statute.
    After careful review, and for the reasons explained below,
    we conclude that the Commissioner’s interpretation of § 1.170A-
    14(g)(6)(ii) is arbitrary and capricious and violates the APA’s proce-
    dural requirements. 1 And because we find the Commissioner’s
    1Because we conclude that § 1.170A-14(g)(6)(ii) is procedurally invalid under
    the APA, we do not reach the Hewitts’ Chevron-related arguments.
    USCA11 Case: 20-13700              Date Filed: 12/29/2021        Page: 4 of 36
    4                            Opinion of the Court                     20-13700
    interpretation of § 1.170A-14(g)(6)(ii) to be invalid under the APA,
    the Easement deed’s subtraction of the value of post-donation im-
    provements from the extinguishment proceeds allocated to the do-
    nee does not violate § 170(h)(5)’s protected-in-perpetuity require-
    ment. Accordingly, we reverse the Tax Court’s order disallowing
    the Hewitts’ carryover deduction for the conservation easement
    and remand for further proceedings.
    I.      FACTUAL AND PROCEDURAL BACKGROUND
    David and Tammy Hewitt 2 reside in Randolph County, Al-
    abama, near Alabama’s border with Georgia. David’s father
    moved to Alabama in the early 1950s, acquiring land there to raise
    cattle, farm, and harvest timber. In the early 1990s, his father trans-
    ferred a portion of this land to David’s sister.
    David subsequently acquired 257.2 acres of land in Ran-
    dolph County (the “Property”) in four transactions. His sister
    transferred approximately 232 acres to David through a series of
    three warranty deeds dated January 27, 1997, January 23, 1998, and
    July 1, 1998. In 2001, David purchased 25 more acres of adjected
    land and bought out the interest of two unrelated persons who co-
    owned a 400-acre parcel with his father. By 2012, David and his
    sister owned approximately 1,325 acres in Randolph and Cleburne
    Counties, Alabama. The cumulative property owned between the
    two siblings had no zoning ordinances at the time of the
    2   We refer to the Hewitts individually by their first names where relevant.
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 5 of 36
    20-13700               Opinion of the Court                       5
    Easement’s grant and consisted of pastureland along a county road
    and wooded areas with steep topography, rough terrain, and lim-
    ited road access. David has used, and continues to use, portions of
    the Property as a cattle ranch.
    On December 28, 2012, David donated the Easement on the
    Property to and for the benefit of Pelican Coast Conservancy, Inc.,
    a wholly owned subsidiary of the Atlantic Coast Conservancy, Inc.
    (collectively, “the Conservancy”), through a document entitled
    Deed of Conservation Easement, which was recorded with the
    Probate Judge for Randolph County the same day. The Easement
    deed provides that the Easement’s purpose is “to assure that the
    Property will be retained forever predominately in its natural con-
    dition and to prevent any use of the Property that will impair or
    interfere with the Conservation Values as set forth in this Ease-
    ment.” The Easement deed sets forth a list of “prohibited uses”
    and permits the Conservancy the right to enter upon the Property
    at reasonable times to preserve and protect the conservation fea-
    tures. The deed also contains a “permitted uses” section, which
    reserved to the Hewitts the right to build certain types of improve-
    ments on certain areas of the Property.
    Additionally, section 15 of the deed governs judicial extin-
    guishment of the Easement. Subsection 15.1 provides:
    Extinguishment. If circumstances arise in the future
    such as render the purpose of this Easement impossi-
    ble to accomplish, this Easement can only be termi-
    nated or extinguished, whether in whole or in part,
    USCA11 Case: 20-13700        Date Filed: 12/29/2021      Page: 6 of 36
    6                      Opinion of the Court                   20-13700
    by judicial proceedings in a court of competent juris-
    diction, and the amount of the proceeds to which
    Conservancy shall be entitled, after the satisfaction or
    prior claims, from any sale, exchange, or involuntary
    conversion of all or any portion of the Property sub-
    sequent to such termination or extinguishment
    (herein collectively “Extinguishment”) shall be deter-
    mined to be at least equal to the perpetual conserva-
    tion restriction’s proportionate value unless other-
    wise provided by Alabama law at the time, in accord-
    ance with Subsection 15.2 . . . .
    In turn, subsection 15.2 provides:
    Proceeds. This Easement constitutes a real property
    interest immediately vested in Conservancy. For the
    purposes of this Subsection, the parties stipulate that
    this Easement shall have at the time of Extinguish-
    ment a fair market value determined by multiplying
    the then fair market value of the Property unencum-
    bered by the Easement (minus any increase in value
    after the date of this grant attributable to improve-
    ments) by the ratio of the value of the Easement at
    the time of this grant to the value of the Property,
    without deduction for the value of the Easement, at
    the time of this grant. . . . For the purposes of this par-
    agraph, the ratio of the value of the Easement to the
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 7 of 36
    20-13700               Opinion of the Court                        7
    value of the Property unencumbered by the Ease-
    ment shall remain constant.
    (emphasis added).
    As stipulated by the parties, the Conservancy provided Da-
    vid with a contemporaneous written acknowledgement within the
    meaning of I.R.C. § 170(f)(8), and the Conservancy was a “qualified
    organization” within the meaning of I.R.C. § 170(h)(3) at the time
    of the Easement donation. The Commissioner also does not con-
    test that the Property complied with the requirements of I.R.C.
    § 170(h)(4)(A)(ii)–(iii).
    While David is the sole owner of the Property, the Hewitts
    jointly filed their tax returns for the relevant tax years at issue—
    2012, 2013, and 2014. For the 2012 tax year, the Hewitts reported
    a noncash, charitable contribution for the donation of the Ease-
    ment in the amount of $2,788,000. An appraisal of the Easement
    was attached to their 2012 return, which the Commissioner—only
    for the purposes of this appeal—does not contest was a qualified
    appraisal prepared by a qualified appraiser as required by I.R.C. §
    170(f)(11)(E). However, the Hewitts and the Commissioner do not
    stipulate to the appraisal’s contents. Due to limitations on charita-
    ble contribution deductions, the deduction for the Easement con-
    tribution was $57,738.
    The Hewitts timely filed their federal income tax returns for
    the 2013 and 2014 tax years. The 2013 return claimed a noncash,
    charitable contribution carryforward deduction from the 2012
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 8 of 36
    8                      Opinion of the Court                20-13700
    charitable contribution deduction for the Easement in the amount
    of $1,868,782, and the 2014 return carried the same deduction in
    the amount of $861,480.
    On August 16, 2017, the Commissioner timely mailed a stat-
    utory notice of deficiency (“NOD”) for the 2013 and 2014 taxable
    years to the Hewitts. The NOD provided that the Hewitts owed:
    (1) a $336,894 tax deficiency and an I.R.C. § 6662 penalty of
    $134,757.60 for the 2013 year; and (2) a $347,878 tax deficiency and
    $136,458.40 penalty for the 2014 year. The NOD disallowed
    $2,730,262 of the charitable contribution carryover deduction from
    2012 for 2013 and 2014.
    On November 14, 2017, the Hewitts timely filed a petition
    for redetermination with the Tax Court, challenging the disallow-
    ances for the carryover deductions related to the Easement in the
    NOD. In a pretrial memorandum, the Commissioner argued that
    the Easement deed failed to comply with 
    Treas. Reg. § 1
    .170A-
    14(g)(6) due to an “improvements clause” included therein. The
    case proceeded to trial. In their post-trial brief, the Hewitts con-
    tended, among other things, that § 1.170A-14(g)(6)(ii), as inter-
    preted by the Commissioner, was not a valid exercise of Treasury’s
    rulemaking authority.
    On June 17, 2020, the Tax Court issued a memorandum
    opinion determining that the Hewitts were not entitled to carryo-
    ver the charitable contribution deduction for the donation of the
    USCA11 Case: 20-13700          Date Filed: 12/29/2021        Page: 9 of 36
    20-13700                 Opinion of the Court                             9
    Easement. 3 The Tax Court explained that section 15 of the deed
    “subtracts the value of posteasement improvements before deter-
    mining the Conservancy’s share of the extinguishment proceeds
    and fails to allocate the extinguishment proceeds in accordance
    with” § 1.170A-14(g)(6), as that regulation “does not permit the
    value of posteasement improvements to be subtracted from the
    proceeds before determining the donee’s share.” The Tax Court
    rejected the Hewitts’ argument that an easement donee’s right to
    any extinguishment proceeds is limited to those from the property
    as it existed at the time of the grant as contrary to the regulation’s
    text. Therefore, the Tax Court explained that “[f]or purposes of
    the extinguishment provisions, the subject property may change,
    but the donee’s property right to the extinguishment proceeds may
    not.” The Tax Court also rejected the Hewitts’ challenge to §
    1.170A-14(g)(6)(ii)’s procedural and substantive validity based on
    its decision in Oakbrook Land Holdings, LLC v. Comm’r, 
    154 T.C. 180
     (2020).
    This appeal ensued.
    II.     STANDARD OF REVIEW
    We review the Tax Court’s legal conclusions de novo and
    its factual findings for clear error. Kardash v. Comm’r, 
    866 F.3d 1249
    , 1252 (11th Cir. 2017).
    3 The Tax Court found the Hewitts were not liable for the penalties assessed
    against them in the NOD, and the Commissioner does not challenge this rul-
    ing on appeal.
    USCA11 Case: 20-13700            Date Filed: 12/29/2021   Page: 10 of 36
    10                      Opinion of the Court                  20-13700
    III.      ANALYSIS
    Under the APA, a “reviewing court shall . . . hold unlawful
    and set aside agency action, findings, and conclusions found to
    be . . . arbitrary, capricious, an abuse of discretion, or otherwise not
    in accordance with law.” 
    5 U.S.C. § 706
    (2)(A). Our review stand-
    ard is “narrow,” and we “will not substitute [our] judgment for that
    of the agency.” Lloyd Noland Hosp. & Clinic v. Heckler, 
    762 F.2d 1561
    , 1565 (11th Cir. 1985). However, “[i]n employing this defer-
    ential standard of review,” we do “not rubber stamp the action of
    the agency.” Port of Jacksonville Mar. Ad Hoc Comm., Inc. v. U.S.
    Coast Guard, 
    788 F.2d 705
    , 708 (11th Cir. 1986). Rather, “[w]e must
    determine whether the decision was based on a consideration of
    the relevant factors and whether there was a clear judgment error.”
    Lloyd Noland, 
    762 F.2d at
    1565 (citing Motor Vehicles Mfrs. Ass’n
    v. State Farm Mut. Auto. Ins. Co., 
    463 U.S. 29
    , 43 (1983)). Further-
    more, “[w]e may not supply a reasoned basis for the agency’s ac-
    tion that the agency itself has not given,” although we will “uphold
    a decision of less than ideal clarity if the agency’s path may reason-
    ably be discerned.” State Farm, 
    463 U.S. at 43
     (first quoting SEC v.
    Chenery Corp., 
    332 U.S. 194
    , 196 (1974), then quoting Bowman
    Transp. Inc. v. Ark.-Best Freight Sys., 
    419 U.S. 281
    , 286 (1974)); ac-
    cord Judulang v. Holder, 
    565 U.S. 42
    , 52–55 (2011). And “courts
    may not accept . . . counsel’s post hoc rationalizations for agency
    actions,” as “an agency’s action must be upheld, if at all, on the ba-
    sis articulated by the agency itself.” State Farm, 
    565 U.S. at 50
    .
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 11 of 36
    20-13700               Opinion of the Court                        11
    The APA “prescribes a three-step procedure for so-called
    ‘notice-and-comment rulemaking.’” Perez v. Mortg. Bankers
    Ass’n, 
    575 U.S. 92
    , 96 (2015); accord 
    5 U.S.C. § 553
    . First, an agency
    “must issue a ‘[g]eneral notice of proposed rulemaking,’ ordinarily
    by publication in the Federal Register.” Perez, 575 U.S. at 96 (alter-
    ation in original) (quoting § 553(b)). Second, “if ‘notice [is] re-
    quired,’ the agency must ‘give interested persons an opportunity
    to participate in the rule making through submission of written
    data, views, or arguments,’” and the agency “must consider and
    respond to significant comments received during the period for
    public comment.” Id. (alteration in original) (quoting § 553(c)).
    Third, in promulgating the final rule, the agency “must include in
    the rule’s text ‘a concise general statement of [its] basis and pur-
    pose.’” Id. (alteration in original) (quoting § 553(c)). As the Su-
    preme Court has explained, “Rules issued through the notice-and-
    comment process are often referred to as ‘legislative rules’ because
    they have the ‘force and effect of law.’” Id. (quoting Chrysler Corp.
    v. Brown, 
    441 U.S. 281
    , 302–03 (1979)).
    Thus, “[t]he APA requires the agency to incorporate into a
    new rule a concise general statement of its basis and purpose.”
    Lloyd Noland, 
    762 F.2d at 1566
    . As we have explained, “state-
    ment[s] may vary, but should fully explain the factual and legal ba-
    sis for the rule.” 
    Id.
     Indeed, “[b]asis and purpose statements must
    enable the reviewing court to see the objections and why the
    agency reacted to them as it did,” 
    id.,
     as “[o]ne of the basic proce-
    dural requirements of administrative rulemaking is that an agency
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 12 of 36
    12                     Opinion of the Court                 20-13700
    must give adequate reasons for its decisions,” Encino Motorcars,
    LLC v. Navarro, 
    579 U.S. 211
    , 221 (2016). And, in the statement,
    the agency must rebut “vital relevant” or significant comments.
    See Lloyd Noland, 
    762 F.2d at 1567
    ; Hussion v. Madigan, 
    950 F.2d 1546
    , 1554 (11th Cir. 1992) (“Under the ‘arbitrary and capricious'
    standard of review, an agency is . . . required to respond to signifi-
    cant comments that cast doubt on the reasonableness of the rule
    the agency adopts.” (quoting Balt. Gas & Elec. Co. v. United States,
    
    817 F.2d 108
    , 116 (D.C. Cir. 1987))). The purpose of notice-and-
    comment rulemaking is to “give[] affected parties fair warning of
    potential changes in the law and an opportunity to be heard on
    those changes” while “afford[ing] the agency a chance to avoid er-
    rors and make a more informed decision.” Azar v. Allina Health
    Servs., 
    139 S. Ct. 1804
    , 1816 (2019).
    Turning to the statutory and regulatory tax provisions at
    hand, I.R.C. § 170(a) generally allows taxpayers to deduct certain
    charitable contributions. While a taxpayer normally is not entitled
    to deduct the donation of “an interest in property which consists of
    less than the taxpayer’s entire interest in such property,” id.
    § 170(f)(3)(A), an exception is made for a “qualified conservation
    contribution,” id. § 170(f)(3)(B)(iii), (h); accord TOT, 1 F.4th at
    1361. Congress created this exception, codified at I.R.C.
    § 170(f)(3)(B)(iii), (h), in 1980. Tax Treatment Extension Act of
    1980, Pub. L. No. 96-541, § 6, 
    94 Stat. 3204
    , 3206; Oakbrook, 
    154 T.C. at 185
    . Under § 170(h), for a contribution to be a “qualified
    conservation contribution,” the contribution must be “(A) of a
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 13 of 36
    20-13700               Opinion of the Court                        13
    qualified real property interest, (B) to a qualified organization, (C)
    exclusively for conservation purposes.” § 170(h)(1). A “qualified
    real property interest” includes “a restriction (granted in perpetu-
    ity) on the use which may be made of the real property.”
    170(h)(2)(C). Additionally, § 170(h)(5)(A) provides that, for pur-
    poses of subsection (h), “[a] contribution shall not be treated as ex-
    clusively for conservation purposes unless the conservation pur-
    pose is protected in perpetuity.” The statute, however, does not
    define the “protected in perpetuity” requirement. TOT, 1 F.4th at
    1362.
    On May 23, 1983, Treasury issued a notice of proposed rule-
    making with “proposed regulations relating to contributions of
    partial interests in property for conservation purposes.” Qualified
    Conservation Contribution; Proposed Rulemaking, 
    48 Fed. Reg. 22,940
    , 22,940 (May 23, 1983). Then, on January 14, 1986, Treasury
    issued final regulations, including the regulation at issue in this
    case—
    Treas. Reg. § 1
    .170A-14(g)(6)—governing the allocation of
    proceeds between the donor and donee in the event of judicial ex-
    tinguishment of a donated conservation easement. Income Taxes;
    Qualified Conservation Contributions, 
    51 Fed. Reg. 1496
     (Jan. 14,
    1986). Section 1.170A-14(g)(6), titled “Extinguishment,” provides:
    (i) In general. If a subsequent unexpected change in
    the conditions surrounding the property that is the
    subject of a donation under this paragraph can make
    impossible or impractical the continued use of the
    property for conservation purposes, the conservation
    USCA11 Case: 20-13700      Date Filed: 12/29/2021     Page: 14 of 36
    14                    Opinion of the Court                 20-13700
    purpose can nonetheless be treated as protected in
    perpetuity if the restrictions are extinguished by judi-
    cial proceeding and all of the donee’s proceeds (deter-
    mined under paragraph (g)(6)(ii) of this section) from
    a subsequent sale or exchange of the property are
    used by the donee organization in a manner con-
    sistent with the conservation purposes of the original
    contribution.
    (ii) Proceeds. . . . [F]or a deduction to be allowed un-
    der this section, at the time of the gift the donor must
    agree that the donation of the perpetual conservation
    restriction gives rise to a property right, immediately
    vested in the donee organization, with a fair market
    value that is at least equal to the proportionate value
    that the perpetual conservation restriction at the time
    of the gift, bears to the value of the property as a
    whole at that time. . . . For purposes of this para-
    graph (g)(6)(ii), that proportionate value of the do-
    nee’s property rights shall remain constant. Accord-
    ingly, when a change in conditions give rise to the ex-
    tinguishment of a perpetual conservation restriction
    under paragraph (g)(6)(i) of this section, the donee or-
    ganization, on a subsequent sale, exchange, or invol-
    untary conversion of the subject property, must be
    entitled to a portion of the proceeds at least equal to
    that proportionate value of the perpetual
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 15 of 36
    20-13700               Opinion of the Court                        15
    conservation restriction, unless state law provides
    that the donor is entitled to the full proceeds from the
    conversion without regard to the terms of the prior
    perpetual conservation restriction.
    To summarize, “the regulations require that the donee of an
    easement be granted a vested right to the value of judicial sale pro-
    ceeds (e.g. in condemnation) multiplied by ‘a fraction equal to the
    value of the conservation easement at the time of the gift, divided
    by the value of the property as a whole at that time.’” TOT, 1 F.4th
    at 1362 (quoting PBBM-Rose Hill, 900 F.3d at 207). And, in TOT,
    we found that § 1.170A-14(g)(6)(ii)’s proceeds formula “does not al-
    low for ‘any increase in value after the date of th[e] grant attribut-
    able to improvements’ to be subtracted from the extinguish-
    ment . . . proceeds before the fraction is applied to the proceeds.”
    Id. at 1363 (alteration in original). But while we agreed with the
    Commissioner’s interpretation of the proceeds regulation in TOT,
    we expressly did not consider the validity of the regulation under
    the APA, as the taxpayers there did not make such a challenge. Id.
    at 1362 n.13; see also PBBM-Rose Hill, 900 F.3d at 209 n.8 (declining
    to address a challenge to § 1.170A-14(g)(6)(ii)’s validity as the tax-
    payer failed to make the argument below).
    Unlike TOT, the Hewitts assert that Treasury failed to com-
    ply with the procedural requirements of the APA in promulgating
    
    Treas. Reg. § 1
    .170A-14(g)(6)(ii). Specifically, the Hewitts contend
    that the administrative record demonstrates that comments raising
    concerns with § 1.170A-14(g)(6)(ii) were filed during the
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 16 of 36
    16                     Opinion of the Court                20-13700
    rulemaking process, that those comments were “significant” such
    that they required a response from Treasury, and that Treasury
    failed to adequately respond to those significant comments in the
    final regulation’s “basis and purpose” statement, in violation of the
    APA’s procedural requirements. As such, the Hewitts contend that
    § 1.170A-14(g)(6)(ii), as interpreted by the Commissioner to pro-
    hibit the subtraction of the value of post-donation improvements
    to the easement property in the proceeds allocated to the donee in
    the event of judicial extinguishment, is arbitrary and capricious un-
    der the APA.
    As previously noted, Treasury issued a notice of proposed
    rulemaking following Congress’s enaction of § 170(h) for “pro-
    posed regulations relating to contributions of partial interests in
    property for conservation purposes” and to clarify “the statutory
    rules in effect under [the Tax Treatment Extension Act of 1980].”
    48 Fed. Reg. at 22,940. One of the subparagraphs in the proposed
    regulations ultimately became § 1.170A-14(g)(6). Id. at 22,946–47.
    Of relevance here, the preamble to the proposed rulemaking ex-
    plained that section 6 of that act “made extensive changes in the
    existing statute, eliminated the expiration date, and incorporated
    the relevant language into a new section 170(h).” Id. at 22,940. It
    further provided that “[t]he regulations reflect[ed] the major policy
    decisions made by the Congress and expressed in . . . committee
    reports.” Id. And Treasury stated that it would consider any writ-
    ten comments submitted before adopting the proposed regula-
    tions. Id. at 22,941.
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 17 of 36
    20-13700               Opinion of the Court                       17
    Following Treasury’s request for public comments, it re-
    ceived more than 700 pages of commentary from ninety organiza-
    tions and individuals. Of the ninety commenters, thirteen offered
    comments as to the proposed extinguishment proceeds regulation.
    Oakbrook, 
    154 T.C. at 186
    . The Hewitts contend that seven of
    those thirteen commenters “expressed concern that allocation of
    post-extinguishment proceeds under the proposed Proceeds Regu-
    lation was unworkable, did not reflect the reality of the donee’s in-
    terest, or could result in an unfair loss to the property owner and a
    corresponding windfall for the donee.”
    Turning to the most detailed comment, the New York Land-
    marks Conservancy (“NYLC”) urged Treasury to delete the pro-
    posed proceeds regulation because it contained pervasive “prob-
    lems of policy and practical application.” NYLC stated that while
    Congress enacted the statute “to encourage the protection of [the]
    . . . environment through the donation of conservation re-
    strictions,” the proposed regulation “would thwart the purpose of
    the statute by deterring prospective donors,” as those donors
    would “likely . . . be discouraged from making a donation which
    may tie themselves or future owners to share proceeds of a sale or
    exchange with the charitable organization [donee] under circum-
    stances which cannot possibly be foreseen.” NYLC explained that
    prospective donors frequently were concerned about “perpetuity”
    issues, which were “mollified upon the donor’s recognition that
    common law permits the extinguishment of restrictions when they
    no longer serve the original intended purposes.” But NYLC
    USCA11 Case: 20-13700       Date Filed: 12/29/2021     Page: 18 of 36
    18                     Opinion of the Court                 20-13700
    believed “[t]he prospect of extinguishment would no longer mol-
    lify these fears if a split of proceeds under unknown circumstances
    would be required.” As such, and because “the possibility of extin-
    guishment is relatively remote,” NYLC stated it was “unnecessary”
    for Treasury “to provide for allocation of proceeds after extinguish-
    ment.”
    NYLC also specifically commented on the issue of whether
    the value of post-donation improvements to the easement prop-
    erty should be included or excluded from the extinguishment pro-
    ceeds formula contained in the regulation. NYLC stated that the
    regulation’s structure “contemplates that a ratio of value of the
    conservation restriction to value of the fee will be fixed at the time
    of the donation and will remain in effect forever thereafter.” But
    NYLC asserted that the formula “fail[ed] to take into account that
    improvements may be made thereafter by the owner which should
    properly alter the ratio.” In support of its concern, NYLC pre-
    sented a mathematical example, which was based on a fact pattern
    in the proposed regulations, see 48 Fed. Reg. at 22,945, to show
    that requiring the prospective donor to turn over extinguishment
    proceeds attributable to post-donation improvements to the donee
    “would obviously be undesirable to the prospective donor and
    would constitute a windfall to the donee organization.” See Oak-
    brook, 
    154 T.C. at 224
     (Toro, J., concurring in result). Thus, “in
    light of the potential inequities,” NYLC recommended “that the
    proposed proceeds formula be revised to prevent such inequities
    should the . . . Treasury decide to retain the provision” but
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 19 of 36
    20-13700               Opinion of the Court                       19
    “strongly recommend[ed] deletion of the entire extinguishment
    provision.” (emphasis added).
    While NYLC offered the most extensive comments on the
    proposed proceeds regulation—including being the only com-
    menter that addressed the allocation of the value of proceeds at-
    tributable to future improvements by the donor—other comment-
    ers expressed criticism or urged caution as to the proposed extin-
    guishment regulations. The Landmarks Preservation Council of
    Illinois, for example, “urge[d] caution in the treatment of the con-
    cept of ‘extinguishment’ in the regulations,” as “[t]he discussion in
    the regulations of the conditions under which that binding agree-
    ment may be abrogated lends an undesirable air of legitimacy to
    the concept of ‘extinguishment.’” It also warned that the regula-
    tions could “create a potential disincentive to the donation of ease-
    ments,” noting that “[t]he obligation imposed on the donor or sub-
    sequent owner to pay to the donee organization an amount at least
    equal to the original proportionate value of the easement” could
    place “the donor at risk for an amount of money”—e.g., payments
    to a third party lender—“for which he may not be compensated by
    the disposition of the proceeds of sale.” The Land Trust Exchange
    stated that the proposed proceeds regulation “may result in donors
    or donees having to pay real estate transfer taxes” and that it was
    “unnecessary.” The Trust for Public Land stated that it had “seri-
    ous doubts whether the provision . . . could be enforced against
    anyone other than the original donor of the easement” and that
    “the tax benefit rule is a satisfactory means of meeting any concern
    USCA11 Case: 20-13700            Date Filed: 12/29/2021         Page: 20 of 36
    20                         Opinion of the Court                       20-13700
    the IRS may have that a donor might receive the double benefit of
    an easement deduction followed by later recovery of the value do-
    nated.” The Brandywine Conservancy cautioned that the regula-
    tion “may unnecessarily restrict the amount, payable to the holder
    of an easement, if changes in surrounding territory have made the
    easement proportionately more valuable than the retained inter-
    est” and that “[t]he donee should be entitled to proceeds equal to
    the greater of its original proportionate value or its proportionate
    value at the time of the extinguishment.” And the Nature Conserv-
    ancy and the Maine Coast Heritage Trust both mentioned that the
    regulation should be “clear” that the original proportionate value
    is the minimum that a donee will receive in extinguishment pro-
    ceeds. 4
    After a public hearing, Treasury adopted the proposed reg-
    ulations with revisions. 51 Fed. Reg. at 1496. In the preamble to
    the final rulemaking, Treasury stated that “[t]hese regulations
    4 As to the comments from the Brandywine Conservancy, the Nature Con-
    servancy, and the Maine Coast Heritage Trust, the Tax Court in Oakbrook
    presumed that Treasury responded to those organizations’ comments by
    changing the language of the regulation from the donee of the easement being
    vested with a property right having a fair market value “that is a minimum
    ascertainable proportion of the fair market value to the entire property” to a
    fair market value “that is at least equal to the proportionate value that the
    perpetual conservation restriction at the time of the gift, bears to the value of
    the property as a whole at that time.” 
    154 T.C. at 188
     (first quoting 48 Fed.
    Reg. at 22,946, then quoting § 1.170A-14(g)(6)(ii)). But Treasury did not spe-
    cifically explain in the final regulation that its change in the language was in
    response to those organizations’ comments.
    USCA11 Case: 20-13700      Date Filed: 12/29/2021     Page: 21 of 36
    20-13700               Opinion of the Court                      21
    provide necessary guidance to the public for compliance with the
    law and affect donors and donees of qualified conservation contri-
    butions” and that it had “consider[ed] . . . all comments regarding
    the proposed amendments.” Id. In the subsequent “Summary of
    Comments” section, however, Treasury did not discuss or respond
    to the comments made by NYLC or the other six commenters con-
    cerning the extinguishment proceeds regulation. See id. at 1497–
    98; Oakbrook, 
    154 T.C. at 188
     (“The ‘judicial extinguishment’ pro-
    vision is not among the amendments specifically addressed in the
    ‘Summary of Comments.’”). And Treasury stated that “[a]lthough
    a notice of proposed rulemaking which solicited public comments
    was issued, the Internal Revenue Service concluded when the no-
    tice was issued that the regulations are interpretative and that the
    notice and public comment procedure requirement of 5 U.S.C.
    [§] 553 [of the APA] did not apply.” 51 Fed. Reg. at 1498.
    The Hewitts assert that these seven comments—in particu-
    lar, NYLC’s comment—were significant such that they warranted
    a response from Treasury in promulgating the final extinguish-
    ment proceeds regulation. In response, the Commissioner asserts
    that none of the thirteen comments were significant to require a
    response from Treasury because they did not raise any point cast-
    ing doubt on the regulation’s reasonableness.
    Thus, the issue before us is whether Treasury’s failure to re-
    spond to NYLC’s and the other commenters’ concerns about the
    extinguishment proceeds regulation was in violation of the proce-
    dural requirements of the APA. Phrased differently, we must
    USCA11 Case: 20-13700      Date Filed: 12/29/2021    Page: 22 of 36
    22                     Opinion of the Court               20-13700
    determine whether § 1.170A-14(g)(6)(ii), as interpreted by the
    Commissioner to prohibit the subtraction of any amount of pro-
    ceeds attributable to post-donation improvements to the easement
    property in the event of judicial extinguishment, is procedurally
    valid under the APA where: (1) one commenter—NYLC—made
    specific comments raising the improvements issue as it relates to
    extinguishment proceeds and recommended deletion of the provi-
    sion; (2) six other organizations submitted comments criticizing or
    urging caution as to the regulation; and (3) Treasury failed to spe-
    cifically respond to any of those comments, instead simply stating
    that it had considered “all comments.”
    Below, the Tax Court found that the regulation was proce-
    durally valid under the APA, relying on its decision in Oakbrook.
    In Oakbrook, the Tax Court considered the comments Treasury
    received as to “the fact that the ‘proportionate share’ formula [in
    § 1.170A-14(g)(6)(ii)] does not account for the possibility of donor
    improvements.” 
    154 T.C. at 192
    . The Tax Court concluded that
    the proceeds regulation as to the post-donation improvements was
    procedurally valid under the APA. 
    Id. at 195
    . The court first noted
    that it had found the statement “[a]fter consideration of all com-
    ments,” coupled with an administrative record, to be “sufficient to
    find that Treasury had considered the relevant matter presented to
    it.” 
    Id.
     at 191–92 (alteration in original) (citing Wing v. Comm’r,
    
    81 T.C. 17
    , 31–32 (1983)). The Tax Court stated that “[t]he APA
    ‘has never been interpreted to require the agency to respond to
    every comment, or to analy[z]e every issue or alternative raised by
    USCA11 Case: 20-13700        Date Filed: 12/29/2021     Page: 23 of 36
    20-13700                Opinion of the Court                        23
    the comments, no matter how insubstantial.’” 
    Id. at 192
     (quoting
    Thompson v. Clark, 
    741 F.2d 401
    , 408 (D.C. Cir. 1984)). The Tax
    Court further noted that “[o]nly one of the 90 commenters”—
    NYLC—“mentioned donor improvements, and it devoted exactly
    one paragraph to this subject.” 
    Id.
     The Tax Court stated that
    NYLC’s point that donors “are likely to be discouraged from mak-
    ing a donation” was “a supposition that Treasury may reasonably
    have discounted.” 
    Id.
     And it stated that, as to the improvements
    issue, “[t]he administrative record reflects that no substantive alter-
    natives to the final rules were presented for Treasury’s considera-
    tion.” Id. at 193 (alteration in original) (quoting SIH Partners LLLP
    v. Comm’r, 
    150 T.C. 28
    , 44 (2018)). The Tax Court found that
    “NYLC offered no suggestion about how the subject of donor im-
    provements might be handled; it simply recommended ‘deletion of
    the entire extinguishment provision.’” 
    Id.
    As to the final regulations’ preamble, the Tax Court rejected
    the argument that Treasury did not comply with the APA because
    the preamble “did not discuss the ‘basis and purpose’ of the judicial
    extinguishment provision specifically.” 
    Id.
     at 193–94. The court
    explained that “[e]ven where a regulation contains no statement of
    basis and purpose whatsoever, it may be upheld ‘where the basis
    and purpose . . . [are] considered obvious.’” 
    Id. at 194
     (quoting Cal-
    Almond, Inc. v. U.S. Dep’t of Agric., 
    14 F.3d 429
    , 443 (9th Cir.
    1993)). The court noted the final regulations’ preamble “explains
    that they were being promulgated to ‘provide necessary guidance
    to the public for compliance with the law,’ as recently amended by
    USCA11 Case: 20-13700        Date Filed: 12/29/2021      Page: 24 of 36
    24                      Opinion of the Court                  20-13700
    Congress, ‘relating to contributions . . . of partial interests in prop-
    erty for conservation purposes,’” with the proposed regulations’
    preamble stating, “the requirement that conservation easements
    ‘be perpetual in order to qualify for a deduction.’” 
    Id.
     (first quoting
    51 Fed. Reg. at 1496, then quoting 48 Fed. Reg. at 22,940). And it
    found that “[t]he purpose of the ‘judicial extinguishment’ rule is
    plain on its face—to provide a mechanism to ensure that the con-
    servation purpose can be deemed ‘protected in perpetuity’ not-
    withstanding the possibility that the easement might later be extin-
    guished.” Id. (quoting § 1.170A-14(g)(6)(i)). Finally, the Tax Court
    minimized the importance of the extinguishment proceeds provi-
    sion in the context of the final regulations—“one subparagraph of
    a regulation project consisting of 10 paragraphs, 23 subparagraphs,
    30 subdivisions, and 21 examples”—as the APA did not “mandate
    that an agency explain the basis and purpose of each individual
    component of a regulation separately.” Id. Thus, the court con-
    cluded that “[t]he broad statements of purpose contained in the
    preambles to the final and proposed regulations, coupled with ob-
    vious inferences drawn from the regulations themselves, [were]
    more than adequate.” Id.
    The Oakbrook decision was not unanimous. Judge Toro, in
    a concurring in result opinion, found that, if the proceeds regula-
    tion was read in the way proposed by the Commissioner, i.e., to
    bar subtraction of the value of post-donation improvements from
    the extinguishment proceeds, it failed to comply with the APA’s
    procedural requirements. See id. at 216 (Toro, J., concurring).
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 25 of 36
    20-13700               Opinion of the Court                       25
    Judge Toro explained that the “Treasury received more than 700
    pages of comments” during the comment period and that, in the
    final regulations, Treasury responded to those comments and
    other administrative matters in just two of the twelve pages—“six
    columns in the Federal Register”—consisting of the final regula-
    tions. Id. at 221. In his view, it was likely that Treasury “was
    simply following its historical position that the APA’s procedural
    requirements did not apply to these types of regulations,” noting
    that the final regulations referenced Treasury’s belief that they did
    not require notice and comment and that this belief was mistaken.
    Id. at 222.
    Judge Toro then found that the “Treasury failed to ‘respond
    to “significant points” and consider “all relevant factors” raised by
    the public comments.’” Id. at 223 (quoting Carlson v. Postal Regul.
    Comm’n, 
    938 F.3d 337
    , 334 (D.C. Cir. 2019)). Pointing specifically
    to NYLC’s comment, Judge Toro explained that NYLC “made
    clear that, in its view, it would be inappropriate to condition the
    availability of the deduction for a conservation easement on the
    donor’s agreement to turn over to the donee proceeds attributable
    to improvements on the real property interest that the Code per-
    mitted the donor to retain.” 
    Id. at 224
    . He further noted that
    NYLC: (1) “expressly tied its comments” to a specific rule and a
    specific fact pattern in the proposed regulations; (2) explained that
    the proposed proceeds regulation would “thwart the purpose of
    the statute,” which NYLC stated was to “encourage the protection
    of our significant natural and built environment through the
    USCA11 Case: 20-13700         Date Filed: 12/29/2021       Page: 26 of 36
    26                       Opinion of the Court                    20-13700
    donation of conservation restrictions”; and (3) recommended the
    deletion of the provision “or, at the very least, ‘be revised to pre-
    vent . . . [the] inequities’ it had identified.” 
    Id.
     (alterations in origi-
    nal). As such, Judge Toro explained that the administrative record
    left “no doubt” that NYLC’s comment “‘can be thought to chal-
    lenge a fundamental premise’ underlying the proposed agency de-
    cision.” 
    Id.
     (quoting Carlson, 938 F.3d at 344). The proposed reg-
    ulations’ preamble explained that they reflected Congress’s “major
    policy decisions,” and NYLC “in effect countered that the proposed
    rule on future donor improvements was contrary to those policy
    decisions, would lead to inequitable results that were inconsistent
    with the statute, and would deter future contributions.” Id. at 225
    (quoting 48 Fed. Reg. at 22,940). In other words, Judge Toro found
    that NYLC “offered comments that, ‘if adopted, would require a
    change in an agency’s proposed rule,’” and that “were both ‘rele-
    vant and significant,’ [as to] require[e] a response.” Id. (first quot-
    ing Home Box Office, Inc. v. FCC, 
    567 F.2d 9
    , 35 n.58 (D.C. Cir.
    1977), then quoting Grand Canyon Air Tour Coal. v. FAA, 
    154 F.3d 455
    , 468 (D.C. Cir. 1998)).
    Because Treasury did not provide a response to NYLC’s
    comments, Judge Toro concluded that its actions failed to provide
    “an explanation [that] is clear enough that its ‘path may reasonably
    be discerned’” or “provide any insight on ‘what major issues of pol-
    icy were ventilated . . . and why the agency reacted to them as it
    did’ on this point.” 
    Id.
     at 225–26 (alterations in original) (first quot-
    ing Encino Motorcars, 579 U.S. at 221, then quoting Carlson, 938
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 27 of 36
    20-13700               Opinion of the Court                       27
    F.3d at 344). And it was “not the role of the courts to speculate on
    reasons that might have supported” Treasury’s decision. Id. at 226
    (quoting Encino Motorcars, 579 U.S. at 224). Judge Toro also ex-
    plained that the Oakbrook majority’s reasoning as to the issue was
    flawed for several reasons. He explained that courts were “not re-
    quired to ‘take the agency’s word that it considered all relevant
    matters,’” as the majority asserted. Id. at 226–27 (quoting PPG In-
    dus., Inc. v. Costle, 
    630 F.2d 462
    , 466 (6th Cir. 1980)). He further
    noted that “[a] ‘relevant and significant comment’ requires a re-
    sponse, regardless of whether the point is made by many, a few, or
    even a single commenter,” and “a comment does not lose its sig-
    nificance because it is presented succinctly.” Id. at 227 (quoting
    Carlson, 938 F.3d at 347). And, if the scope of the project “was too
    large to permit an appropriate response to all ‘relevant and signifi-
    cant comments,’ then Treasury could have broken the project
    down into smaller parts.” Id.
    In his dissenting opinion, Judge Holmes reached a similar
    conclusion to Judge Toro on the regulation’s procedural invalidity
    under the APA. He concluded that comments from NYLC and
    other organizations “were significant and [were] entitled to an
    agency response.” See id. at 245 (Holmes, J., dissenting). Judge
    Holmes explained that Treasury’s statement that it considered “all
    comments” was not sufficient under the APA, noting that the Fed-
    eral Circuit, in Dominion Resources, Inc. v. United States, 
    681 F.3d 1313
    , 1319 (Fed. Cir. 2012), found a Treasury regulation procedur-
    ally invalid even though Treasury explicitly stated that “it rejected
    USCA11 Case: 20-13700            Date Filed: 12/29/2021         Page: 28 of 36
    28                         Opinion of the Court                       20-13700
    the commentators’ recommendation and brief explanation in gen-
    eral terms of how one of the provisions worked.” 5 Oakbrook, 
    154 T.C. at 245
    –46 (Holmes, J., dissenting). He further explained that
    the final regulations at issue provided even less explanation than
    those in Dominion Resources, as Treasury failed to “even
    acknowledge the relevant comments or expressly state its disagree-
    ment with them” such that there was not even “a minimal level of
    analysis.” 
    Id. at 248
     (quoting Encino Motorcars, 579 U.S. at 2120).
    After careful consideration of the agency record before us,
    the several opinions in Oakbrook and precedent from the Supreme
    Court, and this Court’s interpretation of procedural validity under
    the APA, we conclude that § 1.170A-14(g)(6)(ii)—as read by the
    Commissioner to prohibit subtracting the value of post-donation
    improvements to the easement property from the proceeds allo-
    cated to the donor and donee in the event of judicial extinguish-
    ment—is arbitrary and capricious under the APA for failing to com-
    ply with the APA’s procedural requirements and is thus invalid.
    See §§ 553(c), 706(2)(A).
    5Specifically, the preamble to the regulation at issue in Dominion Resources
    provided that “[c]ommentators suggested that the regulations provide that
    property is taken out of service only if the property is taken out of service for
    depreciation purposes” and that “[t]he final regulations do not adopt the sug-
    gestion concerning when property should be considered taken out of service.”
    See Dominion Res., Inc. v. United States, 
    97 Fed. Cl. 239
    , 256 (2011) (quoting
    
    59 Fed. Reg. 67,187
    , 67,192–93 (Dec. 29, 1994)), rev’d, 
    681 F.3d 1313
     (Fed. Cir.
    2012).
    USCA11 Case: 20-13700        Date Filed: 12/29/2021     Page: 29 of 36
    20-13700                Opinion of the Court                        29
    Our decision in Lloyd Noland is instructive. In that case, the
    plaintiffs challenged a malpractice insurance rule related to Medi-
    care reimbursements that was promulgated by the Secretary of
    Health and Human Services. 
    762 F.2d at 1563
    . In addressing the
    plaintiffs’ challenge, we concluded that the malpractice insurance
    rule was procedurally inadequate under the APA; specifically, it vi-
    olated § 553(c), which we explained requires an agency “to incor-
    porate into a new rule a concise general statement of its basis and
    purpose.” Id. at 1566. The Secretary had failed to respond to com-
    ments that a study the agency relied on, which contained limited
    data that the authors cautioned against generalizing, was unrelia-
    ble. Id. While the Secretary asserted that the objections were ir-
    relevant, we concluded otherwise, such that those comments
    formed the basis of our holding that the malpractice insurance rule
    was arbitrary. Id. at 1566, 1568. We also rejected the Secretary’s
    argument that she addressed certain hospitals’ comments based on
    the rule’s preamble, stating that “[w]e are aware that insurance
    companies generally do not determine insurance rates for malprac-
    tice insurance based upon the financial status of the patients,” and
    that “premiums are ‘incurred primarily for the benefit of the total
    overall patient population and for the protection of facility assets.’”
    Id. at 1566. While the Secretary suggested “that drawing a conclu-
    sion contrary to the comments does not mean they were not con-
    sidered,” we explained that “[b]asis and purpose statements must
    enable the reviewing court to see the objections and why the
    agency reacted to them as it did” and that agencies should rebut
    relevant comments. Id. at 1566–67. Because the Secretary’s
    USCA11 Case: 20-13700        Date Filed: 12/29/2021      Page: 30 of 36
    30                      Opinion of the Court                  20-13700
    response to the rule’s comments were inadequate, we affirmed the
    district courts’ invalidation of the rule. Id. at 1567, 1569; cf. Encino
    Motorcars, 579 U.S. at 2126–27 (“The [agency] said that, in reach-
    ing its decision, it had ‘carefully considered all of the comments,
    analyses, and arguments made for and against the proposed
    changes.’ . . . But when it came to explaining the ‘good reasons for
    the new policy,’ the [agency] said almost nothing. . . . [T]he
    [agency’s] conclusory statements do not suffice to explain its deci-
    sion.” (first quoting 
    76 Fed. Reg. 18,832
    , 18,832 (Apr. 5, 2011), then
    quoting FCC v. Fox Television Stations, Inc., 
    556 U.S. 502
    , 515
    (2009))).
    The Commissioner argues that Lloyd Noland should be dis-
    tinguished because, in that case, we reviewed “a factual, evidence-
    based rule,” while the extinguishment proceeds regulation is based
    on Treasury’s interpretation of § 170(h)(5)’s statutory protected-in-
    perpetuity requirement. But, in Lloyd Noland, we did not hold
    that the requirement that “[b]asis and purpose statements must en-
    able the reviewing court to see the objections and why the agency
    reacted to them as it did”—including responding to significant
    comments—only applies when there is “erroneous data or fact
    finding” underlying the proposed regulation, as the Commissioner
    suggests, and we decline to do so here.
    As in Lloyd Noland, in promulgating the final extinguish-
    ment proceeds regulation, Treasury failed to respond to the rele-
    vant and significant comment from NYLC as to the post-donation
    improvements issue. In the proposed regulations’ preamble,
    USCA11 Case: 20-13700      Date Filed: 12/29/2021     Page: 31 of 36
    20-13700               Opinion of the Court                      31
    Treasury stated that the “regulations reflect the major policy deci-
    sions made by the Congress and expressed in the[] committee re-
    ports” to the Tax Treatment Extension Act of 1980. 48 Fed. Reg.
    at 22,940. One of the policy decisions reflected in those “commit-
    tee reports,” expressly referenced by Treasury, provided that “the
    preservation of our country’s natural resources and cultural herit-
    age is important,” that “conservation easements now play an im-
    portant role in preservation efforts,” and that “provisions allowing
    deductions for conservation easements should be directed at the
    preservation of unique or otherwise significant land areas or struc-
    tures.” S. Rep. No. 96-1007, at 9 (1980). NYLC’s comment recog-
    nized as much, stating that “[t]he statute was enacted by Congress
    to encourage the protection of our significant natural and built en-
    vironment through the donation of conservation restrictions.”
    As to the proposed regulation overall, NYLC stated that the
    proposed regulation “would thwart the purpose of the statute by
    deterring prospective donors” concerned about tying themselves
    to share proceeds of a sale with the donee “under circumstances
    which cannot possibly be foreseen.” Additionally, NYLC specifi-
    cally commented that the regulation’s proceeds formula: (1) “con-
    templates that a ratio of value of the conservation restriction to
    value of the fee will be fixed at the time of the donation and will
    remain in effect forever thereafter”; and (2) “fail[ed] to take into
    account that improvements may be made thereafter by the owner
    which should properly alter the ratio.” And NYLC warned that this
    outcome “would obviously be undesirable to the prospective
    USCA11 Case: 20-13700       Date Filed: 12/29/2021    Page: 32 of 36
    32                     Opinion of the Court                20-13700
    donor and would constitute a windfall to the donee organization”
    and “strongly recommend[ed] deletion of the entire extinguish-
    ment provision,” or at least revised “to prevent such inequities.” In
    other words, NYLC challenged a fundamental premise underlying
    Treasury’s proposed regulations by “in effect counter[ing] that the
    proposed rule on future donor improvements was contrary to
    those policy decisions [mentioned in the proposed regulations],
    would lead to inequitable results that were inconsistent with the
    statute, and would deter future contributions.” See Oakbrook, 
    154 T.C. at 225
     (Toro, J., concurring).
    Simply put, NYLC’s comment was significant and required
    a response by Treasury to satisfy the APA’s procedural require-
    ments. And the fact that Treasury stated that it had considered “all
    comments,” without more discussion, does not change our analy-
    sis, as it does not “enable [us] to see [NYLC’s] objections and why
    [Treasury] reacted to them as it did.” Lloyd Noland, 
    762 F.2d at 1566
    .
    But the Commissioner contends that the APA only required
    Treasury “to respond to significant comments that cast doubt on
    the reasonableness of the rule” it adopted. See Hussion, 
    950 F.2d at 1554
     (quoting Balt. Gas, 
    817 F.2d at 116
    ); see also Vt. Yankee
    Nuclear Power Corp. v. Nat. Res. Def. Council, Inc., 
    435 U.S. 519
    ,
    553 (1978) (“[C]omments must be significant enough to step over
    a threshold requirement of materiality before any lack of agency
    response or consideration becomes of concern. The comment can-
    not merely state that a particular mistake was made . . . ; it must
    USCA11 Case: 20-13700      Date Filed: 12/29/2021    Page: 33 of 36
    20-13700               Opinion of the Court                      33
    show why the mistake was of possible significance.” (alteration in
    original) (quoting Portland Cement Ass’n v. Ruckelhaus, 
    486 F.2d 375
    , 394 (D.C. Cir. 1973))). And the Commissioner claims that
    Treasury’s “primary (if not exclusive) consideration in crafting the
    proceeds regulation was the meaning of the statutory perpetuity
    requirement” and that, as such, NYLC was required “to explain
    why the rule would not further the goal of ensuring that the con-
    servation purpose embodied in the perpetual use restriction would
    be protected in perpetuity as required by the statute.” The Com-
    missioner argues that NYLC’s comment as to post-donation im-
    provements did not address this consideration, and therefore was
    not a significant comment, because the comment was limited to (1)
    the “observation that the regulation would require the donee to
    receive a proportionate amount of the full proceeds,” including any
    proceeds attributable to the donor’s improvements, and (2)
    NYLC’s belief that this situation would be “‘undesirable’ to the do-
    nor” and would result in a “windfall” for the donee.
    While we agree with the Commissioner that Treasury was
    only required to respond to significant comments to comply with
    the APA’s procedural requirements, we disagree with the Commis-
    sioner’s argument that NYLC’s comment was not significant. The
    Commissioner’s claim that the “primary (if not exclusive)” purpose
    in crafting the proceeds regulation was only to interpret
    § 170(h)(5)’s “protected-in-perpetuity” requirement is inconsistent
    with the committee reports Treasury purportedly relied on. As
    identified by NYLC, one of the purported purposes set forth in the
    USCA11 Case: 20-13700            Date Filed: 12/29/2021         Page: 34 of 36
    34                         Opinion of the Court                       20-13700
    committee reports, was to allow deductions for the donation of
    conservation easements to encourage donation for such ease-
    ments. See S. Rep. No. 96-1007, at 9. And NYLC raised the post-
    donation improvements issue, as to extinguishment proceeds, and
    warned that its exclusion in the regulatory scheme would discour-
    age prospective donors from donating conservation easements. In
    other words, NYLC’s comment was specific to, and casted doubt
    on, the reasonableness of the proceeds regulation in light of one of
    Congress’s committee reports which, according to Treasury, was
    “reflected” in the final regulations. 48 Fed. Reg. at 22,940 (“The
    regulations reflect the major policy decisions made by the Con-
    gress and expressed in the[] committee reports.”). Furthermore,
    the final regulations did not limit the purpose of the proceeds reg-
    ulation in the way the Commissioner suggests. We thus decline to
    classify NYLC’s comment as insignificant based on the Commis-
    sioner’s interpretation of Treasury’s primary purpose in crafting
    the proceeds regulation. 6 See State Farm, 
    463 U.S. at 43, 50
     (“‘[W]e
    6 The Commissioner also points to Treasury’s statements, in discussing dona-
    tions of mortgaged property in the final regulations, that § 170(h)(5) “provides
    that the conservation purposes of the donation must be protected in perpetu-
    ity” and that “[i]n response to comments received, . . . the mortgagee must
    subordinate its rights under the mortgage to the right of the qualified organi-
    zation to enforce the conservation purposes of the gift in perpetuity.” 51 Fed.
    Reg. at 1498. The Commissioner argues that these statements show that
    Treasury viewed “the protected-in-perpetuity requirement as requiring ex-
    press protection of the full value of the donee’s interest in order to adequately
    protect the easement’s conservation purposes,” which is “the approach taken
    USCA11 Case: 20-13700          Date Filed: 12/29/2021        Page: 35 of 36
    20-13700                  Opinion of the Court                            35
    may not supply a reasoned basis for the agency’s action that the
    agency itself has not given.’ . . . [C]ourts may not accept appellate
    counsel’s post hoc rationalizations for agency action.” (quoting
    Chenery, 332 U.S. at 196)).
    The Commissioner additionally asserts that Treasury’s revi-
    sions to the proposed proceeds regulation in the final regulation
    support Treasury’s representation that it considered “all com-
    ments” in the final regulations’ preamble. But, as the Commis-
    sioner concedes, the revisions were simply “clarifications” in re-
    sponse to other comments “expressing uncertainty” about the reg-
    ulation’s meaning “rather than substantive changes.” Indeed, the
    proceeds regulation was revised from vesting the donee with a
    property right having a fair market value “that is a minimum ascer-
    tainable proportion of the fair market value to the entire property”
    to a fair market value “that is at least equal to the proportionate
    value that the perpetual conservation restriction at the time of the
    gift, bears to the value of the property as a whole at that time.” See
    Oakbrook, 
    154 T.C. at 188
     (comparing the proposed and final pro-
    ceeds regulations). But this revision does not provide any indica-
    tion that Treasury was responding to NYLC’s significant comment
    in the proceeds regulation.” But Treasury’s discussion of donations of mort-
    gaged property in the final regulations does not reference the proceeds regu-
    lation nor give any indication that Treasury considered the post-donation im-
    provements issue raised by NYLC. We thus find this argument, which specu-
    lates as to the reason of Treasury’s actions, without merit. See State Farm,
    
    463 U.S. at 43
    .
    USCA11 Case: 20-13700       Date Filed: 12/29/2021   Page: 36 of 36
    36                    Opinion of the Court                20-13700
    about the post-donation improvements issue. See Lloyd Noland,
    
    762 F.2d at 1567
    ; Hussion, 
    950 F.2d at 1554
    . We therefore reject
    this argument.
    IV.    CONCLUSION
    Because Treasury, in promulgating the extinguishment pro-
    ceeds regulation, failed to respond to NYLC’s significant comment
    concerning the post-donation improvements issue as to proceeds,
    it violated the APA’s procedural requirements. See Lloyd Noland,
    
    762 F.2d at 1566
    ; see also Oakbrook, 
    154 T.C. at 225
    –27 (Toro, J.,
    concurring). We thus conclude that the Commissioner’s interpre-
    tation of § 1.170A-14(g)(6)(ii), to disallow the subtraction of the
    value of post-donation improvements to the easement property in
    the extinguishment proceeds allocated to the done, is arbitrary and
    capricious and therefore invalid under the APA’s procedural re-
    quirements. Accordingly, we reverse the Tax Court’s order disal-
    lowing the Hewitts’ carryover charitable deductions as to the do-
    nation of the conservation easement and remand for further pro-
    ceedings.
    REVERSED AND REMANDED.