Anne (Sandy) Batchelor-Robjohns v. United States , 788 F.3d 1280 ( 2015 )


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  •                Case: 14-10742       Date Filed: 06/05/2015      Page: 1 of 38
    [PUBLISH]
    IN THE UNITED STATES COURT OF APPEALS
    FOR THE ELEVENTH CIRCUIT
    ________________________
    No. 14-10742
    ________________________
    D.C. Docket No. 1:12-cv-20038-FAM
    ANNE (SANDY) BATCHELOR-ROBJOHNS,
    et al.
    Plaintiffs-Appellees
    Cross-Appellants,
    versus
    UNITED STATES OF AMERICA,
    Defendant-Appellant
    Cross-Appellee.
    ________________________
    Appeals from the United States District Court
    for the Southern District of Florida
    ________________________
    (June 5, 2015)
    Before MARTIN and DUBINA, Circuit Judges, and RODGERS, * District Judge.
    RODGERS, District Judge:
    *
    Honorable Margaret C. Rodgers, Chief United States District Judge for the Northern District of
    Florida, sitting by designation.
    Case: 14-10742       Date Filed: 06/05/2015       Page: 2 of 38
    This is an appeal of a federal income tax refund suit filed by the Estate of
    George Batchelor (“Estate”).1           Counts I and II of the Estate’s three-count
    Complaint involve Batchelor’s personal income taxes for 1999 and 2000. Count
    III concerns the Estate’s attempt to claim a credit for its 2005 income taxes for
    payments it made in settlement of various lawsuits against Batchelor. The district
    court entered judgment in favor of the Estate on Counts I and II and in the
    government’s favor on Count III. The Estate appeals the district court’s judgment
    as to Count III, which we affirm, and the government appeals as to Counts I and II,
    which we reverse.
    I.   Background
    George Batchelor passed away in July 2002. Prior to his death, he owned all
    of the stock in International Air Leases, Inc. (“IAL”), an aviation business which
    bought, sold, repaired, serviced, and leased aircraft and aircraft parts. On February
    10, 1999, Batchelor sold his IAL stock to International Air Leases of Puerto Rico,
    Inc. (“IALPR”), for approximately $502 million. 2 As part of the transaction,
    IALPR gave Batchelor a promissory note for $150 million (“Note”), which was
    secured by IAL assets that had been transferred in the sale, such as aircraft planes
    1
    The Complaint was filed by Plaintiffs Anne-Batchelor-Robjohns, Daniel J. Perraresi, and
    Father Patrick O’Neill, as co-personal representatives of the Estate of George E. Batchelor. The
    Court refers to Plaintiffs collectively as “the Estate.”
    2
    Batchelor’s cost basis in his stock was $35,000. Thus, nearly the entire sales price represented
    long-term capital gain.
    2
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    and engines (“Option Assets”). Batchelor retained an option to buy back the
    Option Assets, and the parties agreed that if Batchelor exercised the option, they
    would reduce the balance of the $150 million Note by a certain negotiated price for
    each asset. On April 1, 1999, Batchelor exercised his option and purchased the
    Option Assets for approximately $92.5 million, which reduced the balance on the
    Note by that amount. IALPR paid off the Note in August 2000. 3 As a result of the
    transaction, Batchelor received capital gains and interest income, and IAL realized
    a capital gain through its sale of the Option Assets. On his 1999 personal income
    tax return, Batchelor declared the income he received from the sale in 1999,
    approximately $483 million, as capital gain, and paid capital gains tax on the
    proceeds.4 On his 2000 personal income tax return, Batchelor declared $18.8
    million of the sale proceeds as capital gain, and an additional $5.8 million as
    interest income on the Note.
    In February 2002, IAL was placed into involuntary bankruptcy. The IRS
    determined that IAL was liable for approximately $100 million in unpaid taxes,
    largely as a result of its attempt to use a tax shelter scheme after the stock sale, and
    3
    The government claims, and the district court found, that Batchelor received $131.2 million of
    the $150 million Note in 1999 and $24.7 million in 2000. Although the total amount Batchelor
    received exceeds the $150 million face value of the Note, $5.8 million of the amount received in
    2000 represented interest on the Note, which Batchelor reported as ordinary income.
    4
    It was later stipulated that Batchelor should have reported part of the 1999 income (about $6.5
    million) from payments on the Note as interest income.
    3
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    issued a notice of deficiency for that amount. Although there was never any
    suggestion that Batchelor was involved in the scheme, the government nevertheless
    sought to collect IAL’s corporate income tax obligation directly from Batchelor
    under a transferee liability theory. 5 This suit is referred to as “Batchelor I.”
    In Batchelor I, the government attempted to prove that the sale of the IAL
    stock rendered IAL insolvent because the transferring parties undervalued the
    Option Assets by approximately $23.5 million, such that Batchelor received excess
    consideration relative to the actual fair market value of the IAL stock.                  The
    government sought to establish the relative values of the IAL stock and Option
    Assets through expert testimony. The district court, however, struck the experts
    based on the government’s failure to comply with the expert disclosure
    requirements under the civil rules of procedure, and granted summary judgment in
    the Estate’s favor. Consequently, the value of the Option Assets was not decided
    in Batchelor I.
    In December 2004, the government sued the Estate based on its
    determination that Batchelor had underreported his capital gains in conjunction
    with the IAL sale on his 1999 and 2000 personal income tax returns. This suit is
    5
    Under 
    26 U.S.C. § 6901
    , the government may collect a tax liability that a taxpayer cannot pay
    from a transferee who has received assets from the taxpayer. Here, the government sought to
    collect IAL’s unpaid corporate income tax from Batchelor, and subsequently from his Estate,
    pursuant to 
    28 U.S.C. § 3304
    (b)(1)(B), which provides that certain transfers for less than fair
    market value will be considered fraudulent as to a debt to the United States.
    4
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    referred to as “Batchelor III.” In that suit, the government argued, as it did in
    Batchelor I, that Batchelor had undervalued the Option Assets by $23.5 million,
    resulting in a tax deficiency of approximately $6.7 million.                           The Estate
    subsequently paid the tax, and the government then dismissed the case without
    prejudice while acknowledging the Estate’s right to sue for a refund.6 Thereafter,
    the IRS denied the Estate’s refund claim, and the Estate filed the instant suit
    seeking a refund of these tax payments in Counts I and II.
    Count III of the Estate’s Complaint concerns settlement payments the Estate
    made in connection with four civil lawsuits. In 2002, both IAL and IALPR sued
    the Estate, seeking to set aside the sale of Batchelor’s stock as a fraudulent
    transfer. In addition, the Estate inherited two suits commenced prior to that sale,
    each stemming from Batchelor’s involvement with Rich International Airways
    (“Rich”). The Estate eventually settled all four lawsuits, and made settlement
    payments totaling $41 million in July 2004.7                The Estate subsequently filed its
    Federal Estate Tax Return and deducted the settlement payments from Batchelor’s
    gross estate as claims against the Estate pursuant to 
    26 U.S.C. § 2053
    (a)(3). The
    6
    To protect its interest in the probate estate, the government filed suit in Batchelor III before the
    IRS had issued a Notice of Deficiency to Batchelor or his Estate for Batchelor’s 1999 and 2000
    income tax returns. After the IRS issued a Notice of Deficiency on April 29, 2005, the Estate
    chose to pay the tax and sue for a refund.
    7
    In 2002, the Estate settled with the Rich plaintiffs for $2 million and $25 million. The Estate
    settled with IALPR for $12 million in 2003, and with IAL for $1 million in 2004.
    5
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    Estate later sought a refund of $8.3 million on its 2005 income tax return for those
    payments pursuant to 
    26 U.S.C. § 1341
    , which the IRS denied and the Estate now
    seeks to recover in Count III.
    During the district court proceedings, the Estate filed a motion for summary
    judgment with respect to Count I on the basis of res judicata, arguing that both
    Batchelor I and its refund claim in Count I of this case involve the same cause of
    action. The government filed a cross-motion for summary judgment on Count III,
    arguing that the Estate should be precluded from taking both an income tax
    deduction and an estate tax deduction for the settlement payments. The district
    court granted both motions. With respect to the Estate’s motion on Count I, the
    court found that res judicata barred the government’s claim because the instant
    case and Batchelor I “arise out of the very same transaction” and because in both
    cases the government sought to establish that the value of the Option Assets
    transferred to Batchelor in 1999 had a higher value than Batchelor had reported.
    Regarding the government’s motion on Count III, the court determined that
    because the Estate deducted the settlement payments from Batchelor’s gross estate
    to reduce its estate tax obligations, the Estate could not also use those payments to
    reduce Batchelor’s personal income tax liability. The case then proceeded to trial
    on Count II, which, like Count I, concerned the effect of the IAL stock sale on
    Batchelor’s personal income taxes. As with Count I, the district court determined
    6
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    that Count II arose from the sale of the Option Assets at issue in Batchelor I, and
    that res judicata precluded the government from contesting the Estate’s refund
    claim. 8 These cross-appeals followed.
    II.     Standards of Review
    The district court’s application of res judicata presents a question of law
    which we review de novo. In re Piper Aircraft Corp., 
    244 F.3d 1289
    , 1295 (11th
    Cir. 2001). Likewise, the district court’s interpretation of a statute – here, various
    provisions of the Tax Code – is also a question of law we review de novo. Comm’r
    v. Neal, 
    557 F.3d 1262
    , 1269 (11th Cir. 2009).
    III.   Analysis
    First, we address the district court’s application of res judicata to Counts I
    and II. Second, we address the Estate’s attempt to claim an income tax deduction
    for the settlement payments at issue in Count III.
    8
    Count I of the Estate’s Complaint concerns Batchelor’s 1999 income tax return. Count II
    focuses on Batchelor’s 2000 income taxes, and involves a proposed increase in Batchelor’s
    capital gains by approximately $5.8 million. On July 21, 2005, the Estate paid the additional tax
    allegedly owed on the proposed increase ($584,637), along with interest, and subsequently
    initiated the instant refund suit. The government later conceded that Batchelor had in fact
    reported the $5.8 million at issue and that no additional tax was owed for 2000, but claimed the
    Estate was not entitled to a refund because the government should be permitted to offset
    Batchelor’s 1999 tax deficiency by the excess amounts paid for 2000. In its Order dated
    November 13, 2013, the district court found that the IRS had erroneously determined that
    Batchelor failed to report the $5.8 million at issue, and that the challenges the government made
    to this refund claim, including its attempt to offset its proposed recalculation of Batchelor’s 1999
    taxes, were barred by res judicata. Our opinion addresses only the district court’s application of
    res judicata.
    7
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    A. Res Judicata
    The district court determined that the government was precluded from
    defending against the Estate’s claim that it had accurately reported the value of the
    Option Assets when calculating Batchelor’s 1999 and 2000 income tax obligations.
    According to the district court, res judicata applies because both this suit and
    Batchelor I “arise out of the very same transaction” and “the government here is
    attempting to establish the exact same thing it sought to prove in Batchelor I: that
    the value of the option assets transferred to Batchelor in 1999 had a higher value
    than Batchelor and IALPR agreed upon.”                The district court also found that
    Batchelor’s 1999 and 2000 income tax obligations could have been raised and
    decided in Batchelor I, such that those claims may not be raised here.
    The government makes two primary arguments on appeal. First, it argues
    that res judicata does not apply because the personal income tax claims against
    Batchelor in this case and the transferee liability claim against IAL in Batchelor I
    are not the same cause of action. Second, the government argues that, even if the
    claims are part of the same cause of action, it could not have asserted the instant
    claims in Batchelor I given that the IRS had not yet issued a Notice of Deficiency
    with respect to the income tax claims against Batchelor at the time the complaint in
    Batchelor I was filed or when the time to amend the pleadings expired. 9 See Piper
    9
    On April 29, 2005, the IRS issued a Notice of Deficiency to the Estate for Batchelor’s 1999 and
    2000 income taxes, which was within the extended statute of limitations on assessment
    8
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    Aircraft Corp., 244 F.3d at 1296 (explaining that res judicata does not bar a claim
    that could not have been raised in the prior action). In response, the Estate argues
    that both Batchelor I and the Estate’s refund claims in Counts I and II arise out of
    the same transaction, i.e., the sale of Batchelor’s stock and subsequent transfer of
    the Option Assets, and that the value of the Option Assets is the critical factual
    issue in both cases. The Estate also argues that the deficiency in Batchelor’s 1999
    and 2000 income taxes existed when Batchelor filed each return in 2000 and 2001,
    such that the government could have pursued a deficiency suit against him in
    Batchelor I, thereby satisfying this particular res judicata requirement. Finally, the
    Estate argues that although the value of the Option Assets was not actually
    resolved in Batchelor I, the government should not be given a second bite at the
    apple with respect to that determination, particularly since it sought to employ the
    same expert witnesses and valuation reports across the two cases. Because we find
    that Batchelor I and the instant suit are not the same cause of action, and therefore
    the instant suit is not barred, we need not address whether the government could
    have pursued its claims in Batchelor I, under a res judicata analysis, even though
    the IRS did not issue a Notice of Deficiency with respect to Batchelor’s 1999 and
    2000 tax returns until the period to amend the pleadings in Batchelor I had expired.
    applicable in this case. This is significant because the Tax Code’s provisions relating to the
    assessment of deficiencies do not permit the government to bring suit to collect a tax deficiency
    until a Notice of Deficiency has been issued and the requisite 90-day period during which the
    taxpayer may file a petition in Tax Court has passed. See 
    26 U.S.C. § 6213
    (a).
    9
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    The primary dispute on appeal is whether the Estate’s refund claims in
    Counts I and II are part of the same cause of action as the transferee liability claim
    in Batchelor I. The party asserting res judicata bears the burden of showing that
    the later-filed suit is barred. In re Piper Aircraft, 244 F.3d at 1296. For a prior
    judgment to bar a subsequent action under the doctrine of res judicata, the
    following requirements must be met: (1) the prior judgment must have been a final
    judgment on the merits; (2) the prior judgment must have been rendered by a court
    of competent jurisdiction; (3) the parties, or those in privity with them, must be
    identical in both suits; and (4) the same cause of action must be involved in both
    cases. Ray v. Tenn. Valley Auth., 
    677 F.2d 818
    , 821 (11th Cir. 1982); Ragsdale v.
    Rubbermaid, Inc., 
    193 F.3d 1235
    , 1238 (11th Cir. 1999). We address only the last
    of these requirements.
    When determining whether the causes of action are the same for purposes of
    res judicata, we consider “whether the primary right and duty are the same in each
    case.” Ragsdale, 
    193 F.3d at 1239
    . Although we have described the “rights and
    duties” test as the “principal” res judicata test, 
    id.,
     we have stressed that courts
    must also consider the factual context of each case along with the “rights and
    duties” at issue. See Manning v. City of Auburn, 
    953 F.2d 1355
    , 1359 (11th Cir.
    1992) (explaining that it is an “oversimplification” to focus on rights and duties
    alone and that we must also compare the factual issues in each case). In general,
    10
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    even if the rights and duties at issue are distinct, where a case “arises out of the
    same nucleus of operative fact, or is based upon the same factual predicate,” as a
    former action, the two cases constitute the same “claim” or “cause of action” for
    purposes of res judicata. Ragsdale, 
    193 F.3d at 1239
    . When applying the “same
    nucleus of operative fact” test, we “look to the factual issues to be resolved [in the
    second lawsuit between the parties] and compare them with the issues explored in
    [the first lawsuit].”   
    Id.
       We apply a pragmatic approach to this analysis by
    comparing the substance of the actions, not their form. See 
    id.
     at 1239 & 1239 n.8.
    Applying these principles, we conclude that res judicata does not preclude
    the government from contesting the Estate’s refund claims. First, the instant case
    and Batchelor I do not share the same nucleus of operative fact. The Estate’s
    refund claims in Counts I and II pertain to Batchelor’s personal income tax
    liabilities for 1999 and 2000. Relevant to that determination are all facts that might
    impact Batchelor’s income tax liability for those particular years, including
    whether he should have treated a portion of the income he received from the IAL
    stock sale as interest on the Note rather than as capital gain, a fact unrelated to
    Batchelor’s potential liability for IAL’s tax obligations as transferee. In contrast,
    the government’s claims in Batchelor I involve IAL’s corporate income tax
    liability. Facts impacting that issue include IAL’s alleged use of a tax shelter
    scheme (in which Batchelor played no role), and IAL’s solvency before and after
    11
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    the transfer, neither of which impact the computation of Batchelor’s own income
    tax obligations. Given the different tax liabilities at issue, the cases are factually
    distinct.
    The Estate argues unconvincingly that both Batchelor I and the instant suit
    involve the same fundamental issue regarding the value of the Option Assets and
    the impact that valuation might have on its eventual tax liabilities, such that the
    cases share the same nucleus of operative fact. The Estate’s focus is too narrow.
    Although it is true that both suits involve a common factual issue, i.e., the value of
    the Option Assets, this is often the case in tax law, where an individual transaction
    may have multiple tax consequences. See Towe v. Comm’r, 
    64 T.C.M. 1424
    , 
    1992 WL 353773
    , at *3 (1992) (noting that “[a] single transaction or series of
    transactions can result in the incidence of both gift and income taxes”). Yet, what
    matters for res judicata purposes is not whether one common factual issue exists
    across two distinct tax liabilities, but whether the two suits constitute the same
    cause of action. Where, as here, the two suits involve different tax liabilities with a
    host of potential issues unique to each type of tax, the causes of action cannot be
    the same. Moreover, if we agreed with the Estate and ruled that the existence of
    one such common question across distinct tax liabilities precludes the future
    assessment of a tax liability that has not actually been litigated, our decision would
    potentially preclude the IRS, through an overly-broad interpretation of res judicata,
    12
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    from collecting unpaid taxes for distinct tax liabilities linked only by a particular
    common transaction (from among potentially dozens of transactions in a given
    year’s tax). This would be an unworkable result, and would not square with the
    Tax Code’s detailed statutory scheme on assessments. See Michael v. Comm’r, 
    75 F.2d 966
    , 969 (2d Cir. 1935) (rejecting taxpayers’ argument “that in one
    proceeding there must be determined the liability of the petitioner for his own taxes
    and his liability . . . for the taxes of all other taxpayers” because such a rule “would
    involve great difficulty in its administration and would practically render valueless
    the provision of the law which grants a longer period in which to assert the liability
    of a transferee of assets”). 10
    We reach the same outcome under the rights and duties test. Here, we find it
    significant that the instant case involves Batchelor’s individual income tax liability
    under the statutory provisions governing personal income tax obligations,
    including 
    26 U.S.C. §§ 1
    , 6012, 6072, whereas Batchelor I was based on the
    corporate income tax liability imposed on IAL under statutes pertaining to that
    10
    In a related argument, the Estate insists that the tax implications of specific completed
    transactions should be litigated only once. The Estate’s argument, however, rests on principles
    of issue preclusion rather than claim preclusion, and would be more persuasive had the value of
    the Option Assets actually been decided in Batchelor I. See Pleming v. Universal-Rundle Corp.,
    
    142 F.3d 1354
    , 1359-60 (11th Cir. 1998) (noting that for collateral estoppel to apply, the issue
    must have been actually litigated and determined in the prior proceeding); Adolph Coors Co. v.
    Comm’r, 
    519 F.2d 1280
    , 1283 (10th Cir. 1975) (stating that “[t]he doctrine of collateral estoppel
    is strictly applied in tax cases,” and rejecting taxpayer’s attempt to invoke the doctrine where the
    relevant issue had been raised, but not decided, in a previous case).
    13
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    particular tax, including 
    26 U.S.C. § 11
    . Thus, the two suits involve distinct tax
    obligations with a different set of rights and duties. 11                Seeking to define the
    applicable “right” or “duty” more broadly, the Estate argues that the primary right
    at issue in both suits is the government’s right to have the proper values reported
    and taxes paid on a particular transaction. Although in some cases we have
    defined the applicable “right” or “duty” broadly, such as the right to continued
    employment, Ray, 
    677 F.2d at 821-22
    , 12 in other contexts we have focused more
    narrowly on specific statutory rights and duties to determine whether the cases are
    substantively distinct, see, e.g., White v. World Fin. of Meridian, Inc., 
    653 F.2d 147
    , 150 (5th Cir. 1981); 13 I.A. Durbin, Inc. v. Jefferson Nat’l Bank, 
    793 F.2d 1541
    , 1549-50 (11th Cir. 1986).14 In the tax context, which is largely statutory, we
    11
    Although the government sought to collect the unpaid tax directly from Batchelor in Batchelor
    I, his potential liability as transferee does not change the nature of the corporate tax liability at
    issue in Batchelor I.
    12
    In Ray, we found that an employee’s breach of contract claim arising from his termination was
    barred by res judicata due to an earlier suit alleging improper termination in violation of the
    employee’s civil rights because in both suits “the primary right at issue was [plaintiff’s] right of
    continued employment” and the breach of contract claim was substantively identical to the
    earlier civil rights claims. Ray, 
    677 F.2d at 821-22
    .
    13
    All decisions of the former Fifth Circuit issued before October 1, 1981, are binding precedent
    in this circuit. See Bonner v. City of Prichard, 
    661 F.2d 1206
    , 1209 (11th Cir. 1981).
    14
    In White, we rejected the res judicata defense because “[a]lthough the primary right and duty
    in both statutes . . . is identical in that they require [certain bank] disclosures, the nature and
    extent of those disclosures and the remedies afforded for nondisclosure are distinct” under the
    governing statutes, such that the “violations or wrongs” sued for under each statute were
    different. White, 
    653 F.2d at 150
    . In I.A. Durbin, we ruled that plaintiffs’ contempt proceeding
    in bankruptcy court alleging wrongful seizure of personal property did not bar their subsequent
    civil rights suit alleging various constitutional claims based on the same seizure of property
    14
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    believe the latter approach is best. Accordingly, given that each type of tax at issue
    in this case is governed by substantively distinct provisions of the Tax Code, we
    find that the suits derive from different “rights and duties” within the meaning of
    our prior precedent, and thus do not constitute the same cause of action.
    Although the decision in this case is grounded in Eleventh Circuit res
    judicata principles, our determination of whether Batchelor I and the instant suit
    involve the same “cause of action” is guided as well by cases applying res judicata
    in the tax context. The federal income tax is based on a system of annual
    accounting, rather than transactional accounting.            See 
    26 U.S.C. § 441
    . For this
    reason, the United States Supreme Court in Comm’r v. Sunnen, 
    333 U.S. 591
    (1948), recognized, in the context of a personal income tax dispute, that each tax
    year “is the origin of a new liability and of a separate cause of action.” See 
    id. at 598
    . According to Sunnen, “if a claim of liability . . . relating to a particular tax
    year is litigated, a judgment on the merits is res judicata as to any subsequent
    because the primary right in the contempt proceeding was the statutory right “to prevent
    [defendants] from taking possession of the property after the filing of the bankruptcy petition,”
    whereas the civil rights suit implicated the distinct “rights to be free from unreasonable searches
    and seizures and to due process in the taking of their property.” I.A. Durbin, 
    793 F.2d at
    1549-
    50. See also Nash County Bd. of Educ. v. Biltmore Co., 
    640 F.2d 484
    , 487-88 (4th Cir. 1981)
    (stating that res judicata will apply “when the two statutes afford the same right or interdict the
    same wrong,” and finding the defense applicable where “the state and federal statutes upon
    which the two actions are based are identical in language except in the requirement of the federal
    statute, but not of the state statute, of a showing of interstate commerce,” particularly where the
    two suits involve the same wrongful act and operative facts).
    15
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    proceeding involving the same claim and the same tax year.”              
    Id.
     (emphasis
    added). Consistent with Sunnen, this Court has recognized that a taxpayer’s total
    tax liability for a particular type of tax and particular tax year constitutes a single
    cause of action. See Finley v. United States, 
    612 F.2d 166
     (5th Cir. 1980). In
    Finley, we determined that “in federal tax litigation one’s total income tax liability
    for each taxable year constitutes a single, unified cause of action, regardless of the
    variety of contested issues and points that may bear on the final computation,” 
    id. at 170
    , and thus there can only be one suit related to a taxpayer’s tax liability for a
    particular year and particular tax (e.g., a taxpayer’s year 2014 income tax liability).
    See 
    id.
     See also United States v. Davenport, 
    484 F.3d 321
    , 326 (5th Cir. 2007)
    (noting, for purposes of res judicata, that “the tax liability of a particular tax for a
    particular taxable year is a single cause of action”) (internal marks omitted);
    Michael v. Comm’r, 
    75 F.2d 966
    , 969 (2d Cir. 1935) (recognizing that there can
    only be one suit to determine a taxpayer’s individual tax liability for a particular
    year); see also Estate of Hunt v. United States, 
    309 F.2d 146
    , 147-49 (5th Cir.
    1962) (affirming dismissal of taxpayer’s suit for refund of estate taxes because a
    prior refund suit involving the same estate taxes was res judicata as to any
    additional issues that could have been raised with respect to the estate tax). For
    this reason, courts have long held that res judicata does not bar a subsequent tax
    suit unless the suit involves the same tax year and tax liability as a previous one.
    16
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    See S. Bancorporation, Inc. v. Comm’r, 
    847 F.2d 131
    , 136 (4th Cir. 1988) (“In tax
    cases, res judicata is rare, since a prior income tax judgment could only bar a
    subsequent proceeding involving the same claim in the same tax year.”); S-K
    Liquidating Co. v. Comm’r, 
    64 T.C. 713
    , 719 (1975) (finding that a prior suit
    involving the taxpayer’s withholding taxes for calendar years 1968 and 1969 did
    not bar the IRS from pursuing a separate deficiency action for the taxpayer’s
    corporate income tax liability for its fiscal year ending October 31, 1969, because
    “[t]he two taxes and the two taxable periods . . . are different”); Smith v. United
    States, 
    242 F.2d 486
    , 488 (5th Cir. 1957) (holding that res judicata does not apply
    to suits involving monthly excise taxes because “[e]ach month . . . is the origin of a
    new liability and of a separate cause of action”).
    It makes sense that res judicata would not apply to suits involving different
    tax years because the applicable laws and facts pertaining to distinct tax years are
    ever-changing. See Sunnen, 
    333 U.S. at 597-99
    . According to Sunnen, for suits
    involving different tax years, issue preclusion, which precludes litigation of only
    those issues actually determined in the initial suit, is the more appropriate defense,
    albeit one which should be used sparingly and with caution. See 
    id. at 599-600
    ;
    see also Precision Air Parts, 736 F.2d at 1501 (distinguishing res judicata and
    collateral estoppel); Parklane Hosiery Co. v. Shore, 
    439 U.S. 322
    , 327 n.5 (1979)
    17
    Case: 14-10742         Date Filed: 06/05/2015          Page: 18 of 38
    (same). 15 Thus, as one court has explained, “claim preclusion (res judicata) should
    give way to issue preclusion (collateral estoppel) where a different tax year is in
    question, even if the legal issues and facts are otherwise the same.” Burlington N.
    Santa Fe R. Co. v. Assiniboine and Sioux Tribes, 
    323 F.3d 767
    , 771 (9th Cir. 2003)
    (emphasis added). See also, e.g., Cooper v. United States, 
    238 F.2d 40
     (D.C. Cir.
    1957) (finding taxpayer’s income tax refund suit for 1946 through 1950 barred by
    res judicata for 1946 and by collateral estoppel for 1947 through 1950 where
    taxpayer had previously brought suit on his 1946 taxes and lost and same tax issue
    applied across all tax years); Jonas v. Trapp, 
    186 F.2d 951
    , 953-54 (10th Cir.
    1950) (under the doctrine of collateral estoppel, taxpayer could not relitigate issue
    of whether he was a business partner with his wife for his 1941 income taxes when
    the court in a previous suit had rejected taxpayer’s argument as it pertained to his
    1940 income taxes).
    Relevant to the instant suit, courts applying the principles of Sunnen have
    determined that res judicata does not apply to suits involving different types of tax
    liability, even when the suits involve the same underlying transaction, and, at least
    15
    Sunnen explained,
    [I]f a claim of liability or non-liability relating to a particular tax year is litigated,
    a judgment on the merits is res judicata as to any subsequent proceeding involving
    the same claim and the same tax year. But if the later proceeding is concerned
    with a similar . . . claim relating to a different tax year, the prior judgment acts as
    a collateral estoppel only as to those matters in the second proceeding which were
    actually presented and determined in the first suit.
    
    333 U.S. at 598-99
    .
    18
    Case: 14-10742       Date Filed: 06/05/2015     Page: 19 of 38
    in some respects, the same tax year. Frank Sawyer Trust of May 1992 v. Comm’r,
    
    133 T.C. 60
     (2009), is such a case. There, the party attempting to invoke res
    judicata, a trust, owned all of the stock in four corporations involved in the taxi
    business. 
    Id. at 62
    . During the 2000 tax year, the corporations sold substantially
    all of their assets to unrelated third parties, recognizing substantial capital gains.
    
    Id. at 63
    . During the 2000 and 2001 tax year, the trust sold its stock in the
    corporations to a different third party. See 
    id. at 63-65
    . The trust reported the sale
    of its stock on its income tax returns for tax years 2000 and 2001. Thereafter, the
    government sought to collect an alleged tax deficiency directly from the trust for
    unreported gain on the sale of its stock, arguing not only that the trust’s basis in its
    stock was underreported, but also that the stock sale should be recharacterized to
    reflect the reality of the trust having sold the corporations’ assets and having
    retained the sales proceeds for itself, without having paid any tax. 
    Id. at 66-67
    .
    When the initial suit against the trust failed, the government then brought a
    separate action against the trust, as transferee of the corporations, seeking to collect
    the corporations’ unpaid income tax attributable to the corporations’ sale of
    assets. 16 See 
    id. at 67-70
    .
    Although both suits in Frank Sawyer implicated the sale of the corporate
    assets, the Tax Court found that res judicata did not bar the transferee liability
    16
    The government was unable to collect against the corporations because they were insolvent at
    the time the additional taxes were assessed. Frank Sawyer Trust, 133 T.C. at 70.
    19
    Case: 14-10742     Date Filed: 06/05/2015    Page: 20 of 38
    action because the “cause of action” in each case was not the same. See id. at 76 &
    72. According to the court, “[t]he deficiency cases [against the trust] dealt with the
    trust’s gain on the sale of its stock,” and had the government prevailed the trust
    would have been required to pay more tax on the sale of its stock. Id. at 76. The
    trust, however, would not have been required to pay the corporations’ unpaid tax
    liabilities at issue in the transferee action, which arose from the corporations’
    attempts to artificially generate capital losses to offset their capital gains. Id. The
    court emphasized that in the first suit against the trust, the government had not
    attempted to collect the corporations’ unpaid corporate tax.               Accordingly,
    “[a]lthough the deficiency cases [against the trust for its own tax liabilities] and the
    instant action [against the trust as transferee] arise out of similar facts, there [wa]s
    no identity between the causes of action,” and therefore res judicata did not apply.
    Id. at 78 (emphasis added).
    The Tax Court applied this same reasoning nearly twenty years earlier in
    Towe v. Comm’r, 
    64 T.C.M. 1424
    , 
    1992 WL 353773
     (1992), in which it
    determined that an income tax deficiency and a gift tax deficiency were separate
    causes of action for purposes of res judicata, even though each deficiency suit
    arose out of the same transaction and involved the same tax years. In Towe, the
    taxpayers argued that the IRS was precluded from making a gift tax determination
    concerning the same transaction and same taxable periods for which income tax
    20
    Case: 14-10742     Date Filed: 06/05/2015   Page: 21 of 38
    determinations had already been made and judicially resolved. See 
    id.
     at *1-*2
    (noting that “[t]he 1979-81 income tax determinations concerned the same
    transactions (transfers of realty) as the gift tax and transferee determinations”).
    The taxpayers argued that “the [tax] treatment of the transfer of property was the
    subject of earlier litigation and that there was an opportunity to litigate the issue”
    in the earlier case. 
    Id. at *4
    . Rejecting that argument, the court reasoned that “the
    question of whether a particular transaction results in the incidence of gift tax is a
    different issue or cause of action from whether it results in the incidence of income
    tax.” 
    Id. at *5
    . Thus, the court concluded that “[t]he determination of one [tax
    liability] does not preempt the determination of the other . . . even though both
    determinations may concern the same transaction and/or taxable period.”            
    Id.
    Accordingly, the IRS was not precluded by res judicata from making the gift tax
    determinations. 
    Id.
    Frank Sawyer Trust and Towe are distinguishable from those cases where
    res judicata has been applied in transferee liability suits involving a dispute as to
    only one tax liability, including, for example, United States v. Davenport, 
    484 F.3d 321
     (5th Cir. 2007), and Baptiste v. Comm’r, 
    29 F.3d 1533
     (11th Cir. 1994), on
    which the Estate relies.      Davenport involved gifts of stock made by Birnie
    Davenport, who passed away several years after making the gifts to her two
    nephews and a niece without having paid the requisite gift tax. In an initial suit to
    21
    Case: 14-10742        Date Filed: 06/05/2015       Page: 22 of 38
    determine the tax liabilities of Davenport’s estate, the Tax Court found the estate
    liable for unpaid gift tax on Davenport’s stock gifts. The Tax Court valued the
    stock at $2,000 per share, and calculated the tax deficiency owed by the estate
    based on that amount. See Davenport, 
    484 F.3d at 324
    . The estate later failed to
    pay the taxes owed. 
    Id.
     The government then filed suit in federal district court
    against both the estate and the recipients of the stock gifts as transferees pursuant
    to 
    26 U.S.C. § 6324
    (b). 17 The Fifth Circuit found that the two suits involved the
    same operative facts and underlying transactions, as well as the same tax liability
    (i.e., the estate’s gift tax liability), such that both cases involved the same cause of
    action. See 
    id. at 327-28
    . Accordingly, the value of the stock, and the amount of
    gift tax due, could not be re-litigated. 
    Id. at 329
    .
    This Court considered a factually similar case in Baptiste and reached the
    same result. In that case, three brothers each received $50,000 as beneficiaries to
    their father’s life insurance policy upon his death. Baptiste, 
    29 F.3d at 1535
    . After
    the decedent’s estate filed an estate tax return, the IRS determined that the estate
    owed additional estate tax, which the estate contested in Tax Court. 
    Id.
     The
    parties eventually stipulated to the amount of tax owed, and the court entered
    17
    Title 26 of the United States Code section § 6324(b) provides an avenue by which the
    government may pursue a gift tax liability directly from the donee, who may be held personally
    liable for the unpaid gift tax. The statute provides, “If the [gift] tax is not paid when due, the
    donee of any gift shall be personally liable for such tax to the extent of the value of such gift.”
    
    26 U.S.C. § 6324
    (b). See also Davenport, 
    484 F.3d at 325
     (describing section 6324(b) as a
    “transferee liability provision”).
    22
    Case: 14-10742        Date Filed: 06/05/2015       Page: 23 of 38
    judgment in that amount. Id. at 1535-36. After the estate failed to pay the tax, the
    government attempted to collect from the Baptiste brothers as transferees pursuant
    to a statute that, like the gift tax statute at issue in Davenport, makes the recipient
    of the decedent’s property personally liable for the estate tax. See 
    26 U.S.C. § 6324
    (a)(2). Applying res judicata, this Court held that Richard Baptiste, one of the
    Baptiste brothers who resided in Florida, was not permitted to relitigate the value
    of the property for purposes of calculating the amount of estate tax due. See
    Baptiste, 
    29 F.3d at 1539-41
    .                We explained that “[t]he fact that [Richard
    Baptiste’s] purpose is to decrease his personal liability, rather than in the interest of
    the estate, is of no moment. The estate’s liability [for the estate tax] and Baptiste’s
    liability [as transferee] both embrace the same determination – the amount of estate
    tax imposed by chapter 11.”18 
    Id. at 1539
    . See also Egan’s Estate v. Comm’r, 
    260 F.2d 779
    , 780-85 (8th Cir. 1958) (holding res judicata barred transferee of
    corporation from relitigating transferor corporation’s income tax liability for 1948
    for purposes of determining transferee’s liability for that particular tax).
    As with Frank Sawyer Trust and Towe, and unlike Davenport and Baptiste,
    Counts I and II of the instant suit involve different tax liabilities and different
    underlying taxpayers than the claims at issue in Batchelor I. Therefore, the claims
    are not part of the same cause of action, even though they each involve the same
    18
    Although Baptiste appears to be based on issue preclusion, it is still a useful comparison.
    23
    Case: 14-10742      Date Filed: 06/05/2015       Page: 24 of 38
    underlying transaction. 19 For these reasons, we find that the district court erred in
    applying res judicata to bar the government’s claims in Counts I and II and the
    decision must be reversed.
    B.     Settlement Payments
    Count III of the Estate’s Complaint concerns the $41 million in payments
    the Estate made in 2004 to settle various lawsuits against Batchelor. In 2003, the
    Estate deducted the payments from Batchelor’s gross estate as claims against the
    estate pursuant to 
    26 U.S.C. § 2053
    (a)(3). The parties agree that this deduction
    was proper, and Batchelor’s estate tax liability was not at issue before the district
    court. However, after taking the estate tax deduction, the Estate also claimed an
    $8.3 million credit on its 2005 income tax return for the settlement payments. The
    IRS denied the claim, and the Estate then filed the instant suit seeking a refund for
    the perceived overpayment pursuant to 
    26 U.S.C. § 1341
    . The district court
    rejected the Estate’s claim, finding that 
    26 U.S.C. § 642
    (g) barred the Estate from
    claiming both an estate tax deduction under § 2053 and an income tax deduction
    for the same payment. We agree, and therefore affirm the district court’s ruling.
    The Estate’s position is straightforward. According to the Estate, 
    26 U.S.C. § 1341
     entitles it to a return of the taxes Batchelor paid on the $41 million in IAL
    stock proceeds the Estate subsequently returned to IAL, IALPR, and the Rich
    19
    The parties dispute whether the two cases involve the same tax year. We need not resolve that
    issue, however, based on our determination that the underlying tax liabilities are distinct.
    24
    Case: 14-10742       Date Filed: 06/05/2015      Page: 25 of 38
    plaintiffs as settlement payments.            The Estate argues it is not seeking a tax
    windfall, but rather, because the $41 million at issue was originally reported as
    capital gain, by effectively returning that income, it should now be permitted a
    corresponding deduction or credit effectively consisting of a capital loss, and it
    insists § 1341 was designed to accomplish precisely that result. 20 The government
    maintains that the Estate cannot use the $41 million repayment to reduce both its
    estate and income tax obligations, and instead may only deduct the payments from
    either one tax or the other. We agree.
    Section 1341 accounts for the fact that discrete financial transactions
    sometimes implicate multiple tax years. In the ordinary case, deductions on a
    particular item of income are taken during the same year the income is earned and
    reported. See Mooney Aircraft, Inc. v. United States, 
    420 F.2d 400
    , 402-03 (5th
    Cir. 1969). It is not always possible, however, to match income and expenses in
    the same tax year, which may disadvantage the taxpayer due to changing
    circumstances across the two tax years. See 
    id. at 404-05
    ; see also Healy v.
    Comm’r, 
    345 U.S. 278
    , 284 (1953) (noting that when a taxpayer restores an item of
    income in a later tax year, changes in income or fluctuations in tax rates between
    the year of receipt and the year of repayment could disadvantage the taxpayer). In
    North American Oil v. Burnett, 
    286 U.S. 417
     (1932), the United States Supreme
    20
    The Estate calculated a refund of $8,322,466 under § 1341.
    25
    Case: 14-10742    Date Filed: 06/05/2015   Page: 26 of 38
    Court recognized that “[i]f a taxpayer receives earnings under a claim of right and
    without restriction as to its disposition, he has received income which he is
    required to [report], even though it may still be claimed that he is not entitled to
    retain the money, and even though he may still be adjudged liable to restore its
    equivalent.” Id. at 424. This is known as the “claim of right” doctrine. Although
    the taxpayer in North American Oil was eventually entitled to keep the income, id.
    at 421, the Court explained that if the taxpayer, a corporation, “had been obliged to
    refund the [income] received in 1917, it would have been entitled to a deduction
    from the profits of 1922,” the year the dispute regarding the income was resolved.
    Id. at 424. Although this was a hypothetical statement when made in North
    American Oil, the Supreme Court later faced this very scenario in United States v.
    Lewis, 
    340 U.S. 590
     (1951). In that case, an employer gave his employee a
    $22,000 bonus in 1944, which the employee reported as income in 1944. 
    Id. at 590
    . In 1946, a court determined that half of the bonus had to be returned to the
    employer. 
    Id.
     The taxpayer returned the money, and then sought to amend his
    1944 tax return to reduce his income for that year. See 
    id. at 591
    . Consistent with
    what it had said previously in North American Oil, the Supreme Court rejected this
    approach, deciding instead that the proper solution would be to permit a deduction
    in the year of repayment, 1946, for the amount of tax that had been erroneously
    paid in 1944. See 
    id. at 591-92
    . According to Lewis, the tax year in which the
    26
    Case: 14-10742      Date Filed: 06/05/2015       Page: 27 of 38
    contested amount was received could not be reopened, regardless of whether this
    would “result[] in an advantage or disadvantage to a taxpayer.” 
    Id. at 592
    . 21
    Congress later enacted 
    26 U.S.C. § 1341
     to provide a statutory solution to
    the problem presented in cases like Lewis and to account for the tax disparities that
    may exist when a taxpayer claims a deduction in one year for an item of income
    received in an earlier year that the taxpayer was obliged to return.               See United
    States v. Skelly Oil Co., 
    394 U.S. 678
    , 680-81 (1969) (“Section 1341 of the 1954
    Code was enacted to alleviate some of the inequities which Congress felt existed in
    this area”); Maxwell v. United States, 
    334 F.2d 181
    , 183 (5th Cir. 1964)
    (“[O]rdinarily amounts received under a claim of right must be included in taxable
    income in the taxable year of receipt, although repaid in a later year. Section 1341
    was designed to alleviate the harsh effect of this rule”). Under 
    26 U.S.C. § 1341
    ,
    “a taxpayer is entitled to relief if in one year the taxpayer included an item as gross
    income and paid tax on that income, then in a subsequent year is compelled to
    return the item.” Steffen v. United States, 
    349 B.R. 734
    , 738 (M.D. Fla. 2006).
    The purpose of § 1341 is to “put the taxpayer in the same position he would have
    been in had he not included the item as gross income in the first place.” Fla.
    Progress Corp. v. Comm’r, 
    348 F.3d 954
    , 957 (11th Cir. 2003). When § 1341
    applies, the taxpayer is entitled to either a “deduction” or a tax “credit” in the year
    21
    Justice Douglas dissented, noting that the decision might allow the government to exact tax on
    money that was not income to the taxpayer. See Lewis, 
    340 U.S. at 592
     (Douglas, J., dissenting).
    27
    Case: 14-10742    Date Filed: 06/05/2015   Page: 28 of 38
    of repayment; the taxes due for the year the income was received are not affected.
    See 
    26 U.S.C. § 1341
    (a)(4) & (5).
    For § 1341 to apply, the taxpayer must show the following:
    (1)   an item was included in gross income for a prior taxable year
    (or years) because it appeared [at the time the income was
    received] that the taxpayer had an unrestricted right to such
    item;
    (2)   a deduction is allowable for the [current] taxable year because it
    was established after the close of such prior taxable year (or
    years) that the taxpayer did not have an unrestricted right to
    such item or to a portion of such item; and
    (3)   the amount of such deduction exceeds $3,000.
    
    26 U.S.C. § 1341
    (a). In addition to these statutory requirements, a taxpayer must
    demonstrate a “substantive nexus between the right to the income at the time of
    receipt and the subsequent circumstances necessitating a refund.” Steffen, 
    349 B.R. at 738
    . The taxpayer’s return of the income must not be the result of the
    taxpayer’s purely voluntary choice; rather, it must be “established,” for example,
    by a court, that the taxpayer did not have an unrestricted right to the income. See
    
    id. at 739
    . The Tax Court has determined that payments made to settle a lawsuit
    may satisfy this requirement. See Barrett v. Comm’r, 
    96 T.C. 713
     (1991).
    When § 1341 applies, the taxpayer is required to pay the lesser of two
    computed tax payments in the year of repayment. See 
    26 U.S.C. § 1341
    (a) (“the
    tax imposed by this chapter for the taxable year shall be the lesser of” the two
    28
    Case: 14-10742       Date Filed: 06/05/2015       Page: 29 of 38
    computations) (emphasis added). Under the statute’s first method of calculation,
    set forth in subsection (a)(4), the taxpayer simply computes the taxes owed in the
    year of repayment by deducting the restoration payment from his income in that
    year.    
    26 U.S.C. § 1341
    (a)(4).          The second calculation method set forth in
    subsection (a)(5) is more complex, and results in a credit based on the taxes that
    would have been saved in the original year of receipt had the income never been
    received in that year. 22 See 
    id.
     at § 1341(a)(5) & (b); see also Fla. Progress, 
    348 F.3d at 957
     (explaining that the (a)(4) method of calculation results in a deduction
    from the current year’s taxes, whereas the (a)(5) method permits the taxpayer to
    claim a tax credit for the amount his tax was increased in the prior year by
    including the item of income).
    In Fla. Progress, this Court decided, based on the language of the statute
    and its corresponding regulations, that § 1341 does not, by itself, create an
    independent tax deduction and instead applies “only if another code section would
    provide a deduction for the item in the current year.” 
    348 F.3d at 963
    . See also 
    id. at 958-59
     (rejecting the argument that “§ 1341 stands on its own” as a source of a
    22
    Under 
    26 U.S.C. § 1341
    (a)(5), the taxpayer first computes his original, prior year tax with the
    restoration income included (as it was originally calculated in the year of receipt), then
    recomputes his tax for the prior year as if the item had not been included. The taxpayer then
    compares the two resulting tax obligations to determine the amount by which his tax would have
    been reduced had he not originally received the restored income. In the final step, the taxpayer
    reduces his current year’s tax obligation by the amount his tax liability would have been reduced
    in the year of receipt under the re-computation.
    29
    Case: 14-10742        Date Filed: 06/05/2015        Page: 30 of 38
    deduction); see also Alcoa, Inc. v. United States, 
    509 F.3d 173
    , 178 n.4 (3d Cir.
    2007) (“[I]t is a prerequisite for section 1341 treatment that the taxpayer be entitled
    to a deduction for all or part of the repaid amount under some other Code
    section.”). 23 Thus, contrary to the Estate’s argument, we cannot resolve the instant
    dispute simply by reference to § 1341.
    To determine whether “another code section would provide a deduction for
    the item in the current year,” Fla. Progress, 
    348 F.3d at 963
    , the district court
    found, and we agree, that the tax code provisions relating to overlapping estate and
    income tax deductions are relevant. In this context, 
    26 U.S.C. § 642
    (g), entitled
    “Disallowance of double deductions,” generally prevents an estate from claiming
    both an estate tax deduction under 
    26 U.S.C. § 2053
     and an income tax deduction
    for the same payment. The statute provides:
    Amounts allowable under section 2053 or 2054 as a deduction in
    computing the taxable estate of a decedent shall not be allowed as a
    deduction . . . in computing the taxable income of the estate or of any
    other person, unless there is filed . . . a statement that the amounts
    have not been allowed as deductions under section 2053 or 2054 and a
    23
    In finding that § 1341 does not itself create an independent tax deduction, the Court reasoned:
    Subsection (a) of § 1341 provides that “if” three requirements are met, “then” the
    taxpayer is entitled to preferential treatment under [§ 1341]. 
    26 U.S.C. § 1341
    (a)
    (emphasis added). One of those requirements is that “a deduction” be “allowable
    for the taxable year because it was established after the close of such prior taxable
    year . . . that the taxpayer did not have an unrestricted right to such item. . . .” 
    26 U.S.C. § 1341
    (a)(2). The provision itself does not indicate whether a deduction
    should be allowable. That answer must be found in another provision of the code.
    . . . The regulations interpreting this provision confirm this conclusion.
    Fla. Progress, 
    348 F.3d at 958-59
     (emphasis in original).
    30
    Case: 14-10742        Date Filed: 06/05/2015         Page: 31 of 38
    waiver of the right to have such amounts allowed at any time as
    deductions under section 2053 or 2054.
    
    26 U.S.C. § 642
    (g). Section 642 contains an exception, however, for “income in
    respect of decedents.” See 
    id.
     (“subsection [g] shall not apply with respect to
    deductions allowed under part II (relating to income in respect of decedents)”).
    Thus, a double deduction is permitted for “taxes, interest, business expenses, and
    other items accrued at the date of a decedent’s death” that fall within § 2053(a)(3)
    as claims against the estate, as long as they are also allowable under § 691(b). See
    
    26 C.F.R. § 1.642
    (g)-2. Section 691(b), in turn, provides that a decedent’s estate
    may claim both deductions if the expense falls within one of six statutes: sections
    162, 163, 164, 212, 611, or 27.24 The district court in this case properly required
    the Estate to show that one of these statutes applied in order to claim both an estate
    tax deduction under § 2053 and an income tax deduction for the same payment.
    The Estate argues on appeal, as it did in the district court, that sections 162
    and 212 provide the basis for permitting the “double deduction” of the settlement
    payments at issue because the payments arise out of Batchelor’s business activities
    24
    Section 691(b) provides, in pertinent part:
    The amount of any deduction specified in section 162, 163, 164, 212, or 611 . . .
    or credit specified in section 27 . . ., in respect of a decedent which is not properly
    allowable to the decedent in respect of the taxable period in which falls the date of
    his death, or a prior period, shall be allowed . . . in the taxable year when paid . . .
    to the estate of the decedent.
    31
    Case: 14-10742       Date Filed: 06/05/2015      Page: 32 of 38
    in selling his IAL assets, and thus are ordinary and necessary business expenses.25
    We disagree. The $41 million at issue derives from income Batchelor originally
    reported as capital gain through the sale of his IAL stock. Batchelor’s treatment of
    this income as capital gain determines the character of a subsequent repayment of
    that income pursuant to Kimbell v. United States, 
    490 F.2d 203
     (5th Cir. 1974), in
    which this Court determined that “a payment made by a taxpayer in satisfaction of
    a liability arising from an earlier transaction, on which that taxpayer reported
    capital gain [as here], must be treated as a capital loss at least to the amount of the
    capital gain,” rather than as a § 162 business expense. Id. at 205. It is undisputed
    that Batchelor obtained the $41 million of income as a result of his sale of IAL
    stock. It is also undisputed that the settlement payments were made to resolve
    claims that Batchelor had received excess consideration in selling his interest in
    IAL, such that the Estate’s repayments are sufficiently linked to Batchelor’s
    original receipt of income. 26 Accordingly, Kimbell does not permit the Estate to
    25
    
    26 U.S.C. § 162
    (a) provides, “There shall be allowed as a deduction all the ordinary and
    necessary expenses paid or incurred during the taxable year in carrying on any trade or
    business.” 
    26 U.S.C. § 212
     similarly provides, “In the case of an individual, there shall be
    allowed as a deduction all the ordinary and necessary expenses paid or incurred during the
    taxable year . . . (1) for the production or collection of income.” Although the provisions are
    similar, unlike § 162(a), § 212 lacks a “trade or business” requirement. See Estate of Yaeger,
    
    889 F.2d 29
    , 33 (2d Cir. 1989).
    26
    The Estate concedes that if IAL was rendered insolvent by the stock sale and Batchelor
    received excess consideration, he was liable to return it to IAL or its creditors, including the
    plaintiffs in the four unrelated suits against Batchelor. Thus, we find that the amounts paid in
    settlement of those suits are sufficiently linked to the initial income so as to trigger Kimbell.
    32
    Case: 14-10742       Date Filed: 06/05/2015      Page: 33 of 38
    claim a deduction under § 162, and the Estate thus fails to satisfy § 691(b) by way
    of § 162.
    The Estate also attempts to satisfy § 691(b) by invoking § 212, which, in
    pertinent part, permits a deduction to “an individual” for “ordinary and necessary
    expenses paid or incurred during the taxable year . . . for the production or
    collection of income.” 
    26 U.S.C. § 212
    (1). In this Circuit, however, Ҥ 162(a) and
    212 are . . . considered in pari materia;” thus, “the restrictions and qualifications
    applicable to the deductibility of trade or business expenses [under § 162] are also
    applicable to expenses covered by section 212.” Sorrell v. Comm’r, 
    882 F.2d 484
    ,
    487 (11th Cir. 1989) (quoting Fishman v. Comm’r, 
    837 F.2d 309
    , 311 (7th Cir.
    1988), cert. denied, 
    487 U.S. 1235
     (1988)); Estate of Meade v. Comm’r, 
    489 F.2d 161
    , 164 n.6 (5th Cir. 1974) (“For purposes of this distinction between capital
    expenses and ordinary expenses, sections 162 and 212 are construed in the same
    manner . . . .”). Moreover, the rationale of Kimbell – that a taxpayer who initially
    reported income as capital gain may not receive the tax windfall that would result
    by recharacterizing a related expense as an ordinary business expense – applies
    with equal force to § 212. 27 See Estate of Meade, 489 F.2d at 163-66 (taxpayers
    who received settlement payments in a lawsuit and reported those proceeds as
    27
    The parties dispute whether Batchelor’s liability accrued before his death. Having determined
    that the Estate’s proffered income tax deduction is not allowable under section 691(b), we need
    not address this argument.
    33
    Case: 14-10742     Date Filed: 06/05/2015   Page: 34 of 38
    capital gain were not permitted to deduct their legal fees associated with the suit as
    payments for the production of income under § 212). Thus, the Estate’s attempt to
    invoke § 212 also fails.
    In an attempt to circumvent the statutes, the Estate insists it should be
    allowed a double deduction because otherwise the government will receive a
    windfall from the income taxes Batchelor paid on the $41 million at issue. In
    effect, the Estate urges us to fashion an equitable result; however, doing so would
    require us to either disregard § 642(g), or to construe § 691(b) as though it also
    included § 1341 as an exception, neither of which we can do.              The double
    deduction the Estate seeks is plainly prohibited by 
    26 U.S.C. § 642
    (g), see Estate
    of Luehrmann v. Comm’r, 
    287 F.2d 10
    , 12-13 (8th Cir. 1961) (recognizing that the
    purpose of § 642(g)’s predecessor statute “was to prevent taxpayers claiming the
    same items of administration expenses as deductions for both estate income tax
    and estate tax purposes”), and § 1341 is not one of the enumerated exceptions in
    § 691(b). Accordingly, we do not believe Congress intended to allow a double
    deduction based solely upon the potential application of § 1341. See Andrus v.
    Glover Constr. Co., 
    446 U.S. 608
    , 616-17 (1980) (“Where Congress explicitly
    enumerates certain exceptions to a general prohibition, additional exceptions are
    not to be implied, in the absence of evidence of a contrary legislative intent.”).
    See also CBS Inc. v. Prime Time 24 Joint Venture, 
    245 F.3d 1217
    , 1226 (11th Cir.
    34
    Case: 14-10742     Date Filed: 06/05/2015     Page: 35 of 38
    2001) (“‘[W]here Congress knows how to say something but chooses not to, its
    silence is controlling.’”) (quoting In re Griffith, 
    206 F.3d 1389
    , 1394 (11th Cir.
    2000) (en banc)); Harris v. Garner, 
    216 F.3d 970
    , 976 (11th Cir. 2000) (“[T]he
    role of the judicial branch is to apply statutory language, not to rewrite it.”). Thus,
    even assuming the equities actually favor the Estate, such concerns cannot trump
    the applicable statutes. See Long v. Comm’r, 
    772 F.3d 670
    , 678 (11th Cir. 2014)
    (“[D]eductions under the Internal Revenue Code are a matter of legislative grace
    and the taxpayer who claims the benefit must . . . ‘clearly establish’ his entitlement
    to a particular deduction.”) (internal marks and citations omitted); Estate of
    Luehrmann, 
    287 F.2d at 15
     (“Tax exemptions and deductions do not turn upon
    general equitable considerations but depend upon legislative grace.           Statutes
    authorizing tax exemptions and deductions are to be strictly and narrowly
    construed.”); Culley v. United States, 
    222 F.3d 1331
    , 1334 (Fed. Cir. 2000) (“It is
    basic tax law that deductions from taxable income, for purposes of computing tax
    due the United States, are matters of statutory grant”).
    Finally, the Estate points to three authorities as grounds for invoking § 1341
    without reference to either 642(g) or 691(b): Revenue Ruling 77-322, which
    permits “[a]n estate [to] utilize . . . section 1341 . . . in computing its tax when it
    restores an item that was previously included in income by the decedent under a
    claim of right;” Estate of Good v. United States, 
    208 F.Supp. 521
     (E.D. Mich.
    35
    Case: 14-10742    Date Filed: 06/05/2015   Page: 36 of 38
    1962), in which the court determined that an estate was entitled to use § 1341 to
    obtain a refund of the income taxes a decedent had paid on income that the
    decedent’s employer later determined had been erroneously paid even though the
    estate also took an estate tax deduction for the repayment; and Nalty v. United
    States, No. 73-1574-B, 
    1975 WL 577
     (E.D. La. Apr. 16, 1975), which followed
    Estate of Good.
    Aside from the fact that these authorities are not binding, see Redwing
    Carriers, Inc. v. Tomlinson, 
    399 F.2d 652
    , 657 (5th Cir. 1968) (noting that
    Revenue Rulings are merely persuasive), we disagree with their rationale. First,
    Estate of Good, Nalty, and Revenue Ruling 77-322 do not account for this Circuit’s
    requirement that a deduction must be allowable under another provision of the Tax
    Code for § 1341 to apply. See Fla. Progress, 
    348 F.3d at 958-59
    . Thus, it is not
    enough to merely conclude that the requirements of § 1341(a)(1)-(3) are met when
    the facts of the case implicate § 642(g). Second, although the Estate’s authorities
    purport to distinguish between the “credit” offered by subsection (a)(5) and the
    “deduction” offered by subsection (a)(4), see Estate of Good, 
    208 F.Supp. at 523
    ;
    Nalty, 
    1975 WL 577
    , at *5 (relying on the same distinction); Rev. Rul. 77-322
    (adopting Estate of Good without supporting explanation), we do not believe §
    642(g)’s prohibition on double deductions would give way to § 1341 regardless of
    whether the Estate claimed a credit or a deduction.          The deduction/credit
    36
    Case: 14-10742    Date Filed: 06/05/2015   Page: 37 of 38
    distinction merely determines how to account for a § 1341 repayment on one’s
    return, nothing more. What matters is not whether a taxpayer may use § 1341 to
    reduce his present year taxes through a tax credit or a deduction, but rather whether
    a reduction in his income taxes is permitted at all (along with a corresponding
    estate tax deduction). In addition, whether a particular application of § 1341 would
    result in more favorable treatment to a taxpayer under subsection (a)(4) or (a)(5)
    depends on the fortuities of a given case, including changing tax rates and tax
    brackets between the year of receipt and the year of repayment. See Missouri Pac.
    R.R. Co. v. United States, 
    423 F.2d 727
    , 729-35 (Ct. Cl. 1970) (discussing the
    legislative history of § 1341 and its alternative methods of calculation in a case
    where the taxpayer’s tax rates varied widely over the tax years in question); cf.
    Skelly Oil Co., 
    394 U.S. at 681
     (noting that, under the claim of right doctrine, “the
    tax benefit from the deduction in the year of repayment might differ from the
    increase in taxes attributable to the receipt; for example, tax rates might have
    changed, or the taxpayer might be in a different tax ‘bracket.’”). We do not
    believe Congress intended the availability of a double deduction under § 642(g) to
    turn on such fortuities. Regardless of whether a taxpayer would be entitled to a
    “deduction” under subsection (a)(4) or a “credit” under subsection (a)(5), section
    642(g) and its accompanying regulations make clear that § 1341 alone does not
    determine whether a taxpayer may reduce both his income and estate tax liabilities
    37
    Case: 14-10742    Date Filed: 06/05/2015   Page: 38 of 38
    for the same outlay without consideration of § 691(b).        Thus, we reject the
    underlying rationale of the Estate’s authorities. Since the Estate has failed to
    identify an applicable deduction identified in § 691(b), we find no error in the
    district court’s determination that the Estate cannot avoid § 642(g)’s bar on double
    deductions, and therefore affirm on Count III.
    Accordingly, we reverse the district court’s judgment in favor of the Estate
    on Counts I and II and affirm the judgment in favor of the government on Count
    III.
    AFFIRMED IN PART; REVERSED IN PART; AND REMANDED.
    38
    

Document Info

Docket Number: 14-10742

Citation Numbers: 788 F.3d 1280

Filed Date: 6/5/2015

Precedential Status: Precedential

Modified Date: 1/12/2023

Authorities (43)

Adolph Coors Company v. Commissioner of Internal Revenue , 519 F.2d 1280 ( 1975 )

Jones v. Trapp , 186 F.2d 951 ( 1950 )

frederick-lamar-harris-danny-chadwick-v-wayne-garner-commissioner-of-the , 216 F.3d 970 ( 2000 )

James D. Ray v. The Tennessee Valley Authority , 677 F.2d 818 ( 1982 )

Florida Progress Corp. v. Commissioner of Internal Revenue , 348 F.3d 954 ( 2003 )

Richard M. Baptiste, Transferee v. Commissioner of Internal ... , 29 F.3d 1533 ( 1994 )

Commissioner v. Neal , 557 F.3d 1262 ( 2009 )

Sandra L. PLEMING, Plaintiff-Appellant, v. UNIVERSAL-RUNDLE ... , 142 F.3d 1354 ( 1998 )

CBS Inc., Fox Broadcasting Co. v. Primetime 24 Joint Venture , 245 F.3d 1217 ( 2001 )

Gordon S. Sorrell, Jr. And June M. Sorrell v. Commissioner ... , 882 F.2d 484 ( 1989 )

Larry Bonner v. City of Prichard, Alabama , 661 F.2d 1206 ( 1981 )

In Re: Leroy Charles Griffith, Debtor. Leroy Charles ... , 206 F.3d 1389 ( 2000 )

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the-nash-county-board-of-education-v-the-biltmore-company-borden-inc , 640 F.2d 484 ( 1981 )

Alcoa, Inc. v. United States , 509 F.3d 173 ( 2007 )

Southern Bancorporation, Inc. v. Commissioner of Internal ... , 847 F.2d 131 ( 1988 )

ia-durbin-inc-a-florida-corporation-and-betty-d-kail-plaintiffs-v , 793 F.2d 1541 ( 1986 )

Michael v. Commissioner of Internal Revenue , 75 F.2d 966 ( 1935 )

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