T.C. Memo. 2021-69

UNITED STATES TAX COURT

CAROL E. HOLLIDAY, Petitioner v. 

COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket No. 23296-17. Filed June 7, 2021.

Steven L. Powell, for petitioner.

Christina D. Sullivan, Gordon P. Sanz, and Yvette Nunez, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

PUGH, Judge: In a notice of deficiency dated August 7, 2017, respondent 

determined the following:1

1 Unless otherwise indicated, all section references are to the Internal 

Revenue Code in effect at all relevant times, and all Rule references are to the Tax 

Court Rules of Practice and Procedure. All monetary amounts are rounded to the 

nearest dollar.

Served 06/07/21
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Year Deficiency

Penalty

sec. 6662(a)

2014 1$26,432 2$5,286

1 Respondent increased this deficiency to $44,939 by filing a motion 

for leave to file amendment to answer pursuant to Rule 41(a), which we 

granted on June 3, 2019.

2 Respondent conceded this penalty.

The issue for decision is whether settlement proceeds petitioner received in 

2014 constitute taxable income. 

FINDINGS OF FACT

Some of the facts have been stipulated and are so found. The stipulated facts 

are incorporated in our findings by this reference. Petitioner resided in Texas 

when she timely filed her petition.

I. Background

Two lawsuits are central to this case. The first is petitioner’s divorce 

proceeding, in which she was represented by J. Beverly and his law firm (divorce 

attorney and malpractice defendants, respectively). The second is petitioner’s 

malpractice lawsuit against her divorce attorney, in which she was represented by 

Lance Kassab (malpractice attorney).

A. Petitioner’s Divorce Proceedings

In March 2010 petitioner’s former spouse filed for divorce. As part of the 

divorce proceedings, petitioner and her divorce attorney participated in mediation. 

[*2]
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[*3] It resulted in petitioner’s executing a mediated settlement agreement. 

Petitioner objected to the mediated settlement agreement, but her objections were 

not sustained by the divorce court.

In April 2012 the divorce court entered the Agreed Final Decree of Divorce 

between petitioner and her former spouse.

In May 2012 petitioner’s divorce attorney filed a motion for a new trial and 

stated that petitioner received $74,864 less than her equal share of the community 

estate. The motion for a new trial was denied. Petitioner’s divorce attorney told 

petitioner he would appeal, but he failed to do so.

B. Petitioner’s Malpractice Lawsuit

In October 2013 petitioner filed a malpractice lawsuit against her divorce 

attorney. She claimed that her divorce attorney’s representation constituted 

negligence and gross negligence and that he breached the duty of fair dealing and 

his fiduciary duties “by influencing * * * [her] to mediate and enter into a 

transaction that was not fair to * * * [her] under the circumstances” and by not 

pursuing an appeal. She later amended the malpractice petition in July and August 

2014 to add claims for deceptive trade practices, treble damages, and attorney’s

fees. 

To support her claims, petitioner included facts in the malpractice petition 

about her former spouse’s retirement plan, the divorce attorney’s alleged failures, 
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[*4] and her stressful experience during the mediation and other parts of the 

divorce litigation. Her August 2014 amendment to the malpractice petition added 

facts to support her deceptive trade practices claim, including that her divorce 

attorney failed to properly plead claims related to her former spouse’s fraud on the 

marital estate.

She sought damages for “pecuniary and compensatory losses”, including 

“damages for past and future mental anguish, suffering, stress, anxiety, 

humiliation, and loss of ability to enjoy life”, as well as punitive damages and 

disgorgement of the attorney’s fees she paid in the divorce proceeding, resulting 

from the malpractice defendants’ conduct.

In October 2014 petitioner and the malpractice defendants entered into a 

settlement agreement. It recited that “while there remain significant disagreements 

as to the merit of the claims and allegations asserted by the Parties to this lawsuit, 

the Parties have agreed to compromise and settle such claims and allegations, 

without any admission of fault or liability on the part of any party.” Under the 

section “Consideration”, the malpractice defendants agreed to pay petitioner 

$175,000 “[i]n consideration for the mutual promises and obligations set forth in

this Release”. Under the section “Release”, the parties released each other from all 

claims related to the malpractice lawsuit “in exchange for the * * * [settlement 

proceeds]”. All claims included those “of whatever kind or character, known or 
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[*5] unknown * * * which * * * [petitioner] may have against * * * [malpractice 

defendants] arising out of or related to the * * * [malpractice lawsuit].” The 

malpractice defendants did not admit liability or fault in the settlement agreement, 

and the parties did not allocate any of the settlement proceeds toward any 

particular claim or type of damages. 

Petitioner received the settlement proceeds of $175,000, from which she 

paid her malpractice attorney’s $73,500 fee; this was effected by the malpractice 

attorney’s receiving the settlement check, deducting his fee, and transferring the 

remaining $101,500 to petitioner.

2

II. Petitioner’s Tax Return and Respondent’s Notice of Deficiency

On her 2014 Form 1040, U.S. Individual Income Tax Return, line 21, 

petitioner reported “[o]ther income” of zero. She acknowledged the receipt of 

$101,500 through an attached Form 1099-MISC Summary and a “Line 21 

Statement” on which she reported “Other Income from Box 3 of 1099-Misc” of 

$101,500. But the Line 21 Statement then subtracts $101,500 with the description 

“Misclassification of Lawsuit recovery of marital assets”, resulting in total other 

income of zero. 

2 Petitioner’s malpractice attorney testified that he was “99 percent sure the 

* * * [malpractice defendants’ malpractice] insurance company paid the entire 

$175,000”; we treat payment here as if the insurance company paid the malpractice 

defendants who in turn paid petitioner. See Old Colony Tr. Co. v. Commissioner, 

279 U.S. 716 (1929); Bintliff v. United States, 462 F.2d 403, 408 (5th Cir. 1972).
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[*6] In the notice of deficiency, respondent determined that petitioner failed to 

include gross income of $101,500 on the basis of the Form 1099-MISC, 

Miscellaneous Income, issued by her malpractice attorney. After reviewing the 

settlement agreement in preparation for trial of this case, respondent amended his 

answer, stating that all $175,000 of the settlement proceeds should have been 

reported on petitioner’s 2014 Form 1040 with a corresponding miscellaneous 

itemized deduction of $73,500 for the payment to her malpractice attorney. This 

amendment resulted in the increased deficiency of $44,939. 

OPINION

Petitioner argues that the settlement proceeds are a nontaxable return of 

capital because they compensate her for the portion of her marital estate that she 

“was rightfully and legally entitled to, but did not receive, due to the legal 

malpractice of * * * [her divorce attorney].”3

 Respondent counters that the

settlement proceeds are taxable income because they compensate petitioner for the 

alleged failings of her divorce attorney and are not excluded from gross income. 

3 Petitioner does not argue that the settlement proceeds should be excluded 

from income under sec. 104(a), which deals with compensation for personal injury, 

or under sec. 1041, which deals with transfers of property between spouses 

incident to divorce. She maintains that the settlement proceeds represent a 

nontaxable return of capital.
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[*7] I. Burden of Proof

Generally, the taxpayer bears the burden of proving that the Commissioner’s 

determinations are erroneous.4

 Rule 142(a); Welch v. Helvering, 290 U.S. 111, 

115 (1933). Petitioner has not contended and the record does not show that the 

burden of proof should shift to respondent under section 7491(a). See Higbee v. 

Commissioner, 116 T.C. 438, 442 (2001). Petitioner therefore bears the burden of 

showing that the settlement proceeds represent what she claims. See Milenbach v. 

Commissioner, 318 F.3d 924, 933 (9th Cir. 2003), aff’g on this issue 106 T.C. 184 

(1996); see also Espinoza v. Commissioner, 636 F.3d 747, 749 (5th Cir. 2011) 

(reiterating that a taxpayer claiming an exclusion of settlement proceeds from 

income “bears the burden of proving that the exclusion is proper”), aff’g T.C. 

Memo. 2010-53; Simpson v. Commissioner, 141 T.C. 331, 339 (2013) (observing 

that taxpayers generally bear the burden of proving that settlement proceeds “fall 

4 In cases involving unreported income, the U.S. Court of Appeals for the 

Fifth Circuit, to which any appeal in this case would ordinarily lie, see sec. 

7482(b)(1)(A), has held that the Commissioner must establish “some predicate 

evidence” connecting the taxpayer with the income-producing activity or 

demonstrating that the taxpayer actually received unreported income for the 

presumption of correctness to attach to the notice of deficiency, see Portillo v. 

Commissioner, 932 F.2d 1128, 1133 (5th Cir. 1991), aff’g in part, rev’g and 

remanding in part T.C. Memo. 1990-68. 

But the parties do not dispute petitioner’s receipt of the $175,000; they 

dispute its tax treatment. Petitioner reported $101,500 of the settlement proceeds 

on the Form 1099-MISC Summary and “Line 21 Statement” attached to her 2014 

Form 1040. And the full $175,000 settlement payment is evidenced by the 

settlement agreement and the parties’ stipulation of that full amount.
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[*8] squarely within the requirements for any exclusion from gross income”), 

aff’d, 668 F. App’x 241 (9th Cir. 2016).

Respondent bears the burden of proof with respect to the increase in the 

deficiency. See Rule 142(a)(1). 

II. Settlement Proceeds: Taxable Income or Nontaxable Recovery of Capital

A. Legal Background

Section 61(a) defines gross income as “all income from whatever source 

derived” and broadly encompasses any accession to a taxpayer’s wealth. 

Commissioner v. Glenshaw Glass Co., 348 U.S. 426, 429-430 (1955). Consistent 

with the broad definition is the corollary that “exclusions from income must be 

narrowly construed.” Commissioner v. Schleier, 515 U.S. 323, 328 (1995)

(quoting United States v. Burke, 504 U.S. 229, 248 (1992) (Souter, J., concurring 

in judgment)); see Wesson v. United States, 48 F.3d 894, 898 (5th Cir. 1995). And 

“as a general rule, when a litigant’s recovery constitutes income, the litigant’s 

income includes the portion of the recovery paid to the attorney as a contingent 

fee.” Commissioner v. Banks, 543 U.S. 426, 430 (2005). 

Generally, recovery of capital is not income. See United States v. Safety 

Car Heating & Lighting Co., 297 U.S. 88, 98 (1936); Milenbach v. Commissioner, 

318 F.3d at 933 (noting that proceeds that represent compensation for lost value or 

capital generally are not taxable); Freeman v. Commissioner, 33 T.C. 323, 327 
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[*9] (1959) (noting that proceeds received “as the replacement of capital destroyed 

or injured rather than for lost profits” are a return of capital and not taxable”); 

see also Wesson v. United States, 48 F.3d at 899 (discussing that compensatory 

damages for personal injuries are excluded from gross income “because, in effect, 

they restore a loss to capital” (emphasis omitted) (quoting Hawkins v. United 

States, 30 F.3d 1077, 1083 (9th Cir. 1994))). 

Whether a payment received in settlement of a claim represents a recovery 

of capital depends on the nature of the claims that were the basis for the settlement. 

See Spangler v. Commissioner, 323 F.2d 913, 916 (9th Cir. 1963), aff’g T.C. 

Memo. 1961-341; see also Sager Glove Corp. v. Commissioner, 36 T.C. 1173, 

1180 (1961) (“The taxability of the proceeds of a lawsuit, or of a sum received in 

settlement thereof, depends upon the nature of the claim and the actual basis of 

recovery.”), aff’d, 311 F.2d 210 (7th Cir. 1962). We have held previously that “an 

amount paid to a taxpayer in order to compensate the taxpayer for a loss that the 

taxpayer suffered because of the erroneous advice of the taxpayer’s tax consultant 

generally is a return of capital and is not includible in the taxpayer’s income.” 

Cosentino v. Commissioner, T.C. Memo. 2014-186, at *31; see also Clark v. 

Commissioner, 40 B.T.A. 333, 335 (1939); Concord Instruments Corp. v. 

Commissioner, T.C. Memo. 1994-248, 1994 WL 232364, at *24-*25. 
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[*10] To determine whether a settlement represents lost profit or lost value, we 

ask: “[I]n lieu of what was the . . . settlement awarded?” Green v. Commissioner, 

507 F.3d 857, 867 (5th Cir. 2007) (quoting Srivastava v. Commissioner, 220 F.3d 

353, 365 (5th Cir. 2000), aff’g in part, rev’g and remanding in part T.C. Memo. 

1998-362), aff’g T.C. Memo. 2005-250. This is a question of fact. Id. at 866-867. 

“Ultimately, the character of the payment hinges on the payor’s dominant reason 

for making the payment.” Id. at 868. “We first look to the language of the 

agreement itself for indicia of purpose”, focusing on “the origin and characteristics 

of the claims settled * * * [in that agreement]”. Id. at 867 (quoting Pipitone v. 

United States, 180 F.3d 859, 862 (7th Cir. 1999)). Where the agreement does not 

mention purpose, the Court may look at other facts that reveal the payor’s intent, 

such as amount paid, evidence adduced at trial, and the factual circumstances that 

led to the agreement. Id. at 867-868; see also Robinson v. Commissioner, 102 T.C. 

116, 126 (1994) (noting that the determination of the nature of the claims settled 

“is generally made by reference to the settlement agreement in light of the 

surrounding circumstances”), aff’d in part, rev’d in part, and remanded on another 

issue, 70 F.3d 34 (5th Cir. 1995). 

B. Petitioner’s Settlement Proceeds

The settlement agreement makes clear that the settlement proceeds were in 

lieu of damages for legal malpractice. The text of the settlement agreement 
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[*11] indicates its purpose was “to compromise and settle * * * [petitioner’s] 

claims and allegations” against malpractice defendants and that payment “in 

exchange for” release of claims related to petitioner’s lawsuit against the 

malpractice defendants.

Petitioner argues that the settlement proceeds are only for those claims that 

involve the marital estate and that they represent compensation for lost value or 

capital because they “are based on her recovery of the property interest that * * * 

[she] rightfully should have received from her divorce as her share of the marital 

estate.”5

 But the settlement agreement says that the settlement proceeds are for the 

release of “all claims * * * of whatever kind or character, known or unknown * * * 

which * * * [petitioner] may have against * * * [malpractice defendants] arising 

out of or related to the * * * [malpractice lawsuit].” Petitioner thus asks us to look 

through the settlement agreement and consider only her claims related to recovery 

of marital property. We decline to look beyond the plain terms of the settlement 

5 Part of petitioner’s argument about the nature of the settlement proceeds is 

based on information from “Plaintiff’s Fourth Amended Response to Defendants’ 

Request for Disclosure & Plaintiff’s Designation of Expert Witnesses” from 

petitioner’s malpractice lawsuit. Petitioner attached a copy of this disclosure to the 

joint stipulation of facts as Exhibit 9-P. Respondent objected to its admission, 

citing petitioner’s failure to comply with Rule 143(g), hearsay, and lack of 

relevance. We sustain respondent’s objections and add that, even if petitioner’s 

exhibit were admitted into evidence, it would not help us to allocate the proceeds 

between excludible and nonexcludible claims. 
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[*12] agreement, and we conclude that the settlement proceeds were to compensate 

her for her attorney’s malpractice and therefore are taxable. 

We recently rejected a similar attempt to recharacterize the settlement of a 

legal malpractice claim arising from a personal injury lawsuit. In Blum v. 

Commissioner, T.C. Memo. 2021-18, the taxpayer filed a malpractice claim 

against her personal injury attorney, resulting in a settlement payment from the 

personal injury attorney. She asserted that the settlement payment represented a 

return of capital “in that it compensated her for a loss that she suffered because of 

the erroneous advice of her lawyers, viz, the nontaxable amount she would have 

received had she prevailed in her personal injury lawsuit.” Id. at *12. Focusing on 

the text of the settlement agreement, which specified that it was entered into “for 

the purpose of compromising and settling the disputes”, the Court concluded that 

the settlement payment was not a return of capital to the taxpayer but rather to 

compensate her “for distinct failings by her former lawyers.” Id. at *9, *12. 

Petitioner similarly has failed to convince us that the settlement proceeds 

were meant only to replace her marital property, rather than generally to release the 

malpractice defendants from the various claims and types of damages listed in the 

malpractice petition. We therefore conclude that the settlement proceeds do not 

represent recovery of capital, and we sustain respondent’s determination in the 
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[*13] notice of deficiency that the settlement proceeds are includible in gross

income.6

 

Finally, respondent has met his burden of proof with respect to the increased 

deficiency by showing that the $73,500 that yielded the increased deficiency was 

received by petitioner as settlement proceeds. The record includes uncontested 

evidence (and the parties have stipulated) that the settlement consisted of 

$175,000, of which petitioner’s malpractice attorney retained $73,500 as a fee for 

representing her in the lawsuit. The full amount of the settlement proceeds, 

6 Even if petitioner had convinced us that some of the settlement proceeds 

were meant to replace her purported loss of marital property and that the loss was a 

nontaxable recovery of capital, she failed to provide a basis upon which we can 

allocate the settlement proceeds between that hypothetically nontaxable recovery 

and other taxable amounts. The settlement agreement did not allocate any of the 

settlement proceeds toward any of the various claims or types of damages. We 

may “exercise our judgment to make an allocation” of a settlement payment 

between taxable income and a nontaxable return of capital if the record provides us 

with a basis for such an allocation. See Estate of Taracido v. Commissioner, 72 

T.C. 1014, 1026 (1979). But a taxpayer’s “[f]ailure to show the specific amount of 

the payment allocable to the [excludible] claims * * * results in the entire amount’s 

being presumed not to be excludible.” Pipitone v. United States, 180 F.3d 859, 

864 (7th Cir. 1991) (quoting Wise v. Commissioner, T.C. Memo. 1998-4, 1998 

WL 1705, at *4); see Lawson v. Commissioner, T.C. Memo. 2015-211, at *28-*29

(“Where the agreement is silent as to the basis of the settlement or where the 

agreement does not specify that the payment was for a reason that a court finds to 

be nontaxable, this Court has held the settlement payment to be taxable.”); see also

Espinoza v. Commissioner, 636 F.3d 747, 750-751 (5th Cir. 2011), aff’g T.C. 

Memo. 2010-53; Green v. Commissioner, 507 F.3d 857, 867-870 (5th Cir. 2007), 

aff’g T.C. Memo. 2005-250; Estate of Taracido v. Commissioner, 72 T.C. at 1026-

1027. And certain elements of the settlement proceeds, such as interest, would not 

be excludible under any of petitioner’s offered theories. See sec. 61(a)(4). 
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[*14] including the fee petitioner paid her malpractice attorney, is includible in 

gross income. Commissioner v. Banks, 543 U.S. at 430 (noting that the litigant’s 

income includes the portion of the recovery paid to the attorney as a contingent 

fee).

Accordingly, we sustain respondent’s inclusion of the $175,000 in 

petitioner’s gross income for 2014. Any contentions we have not addressed we 

deem irrelevant, moot, or meritless.

To reflect the foregoing,

An appropriate decision will be 

entered for respondent as to the deficiency 

and for petitioner as to the section 6662(a) 

penalty.