Recent developments in individual taxation

By David R. Baldwin, CPA; Robert Caplan, CPA; Shannon Hudson, CPA; David H. Kirk, CPA/PFS; Jennifer S. Korten, CPA; Frank Lin, CPA; Dana McCartney, CPA; Darren Neuschwander, CPA; Jeffrey A. Porter II, CPA; and Donald J. Zidik Jr., CPA



  • Among other notable developments in individual taxation occurring during the six months ending May 2020, the Coronavirus Aid, Relief, and Economic Security (CARES) Act suspended the limitation on excess business losses for passthrough businesses and sole proprietorships for the 2018, 2019, and 2020 tax years.
  • Enacted in December, the Setting Every Community Up for Retirement Enhancement (SECURE) Act provides that most beneficiaries of IRAs and qualified plans must withdraw all money from inherited accounts within 10 years. The new rule generally applies with respect to plan participants or IRA owners who die after Dec. 31, 2019.
  • The Tax Court denied taxpayers a charitable deduction related to a conservation easement because 11 single-family homes were permitted to be built on the 500-acre property.
  • The Tax Court denied a taxpayer a net operating loss deduction for failure to file a concise statement with the tax return setting forth the pertinent facts, as required by regulation.
  • The Tenth Circuit case held that a married couple were not insolvent and thus could not avoid tax on $160,000 of discharged student loans because they exercised effective control over funds they had moved to a savings account owned by their son.
  • In a revenue ruling, the IRS clarified how to calculate the income recognized upon the sale of life insurance contracts.
  • The Tax Court found that a business that bred and raised horses for equestrian competition had a profit motive despite years of reported losses.

This article is a semiannual review of recent developments in the area of individual federal taxation. It covers cases, rulings, and guidance on a variety of topics issued during the six months ending May 2020. The items are arranged in Code section order.

Constitutional challengeIn 2020, the Supreme Court agreed to hear a major challenge to the Patient Protection and Affordable Care Act (PPACA).1 The case the justices will hear was brought by Texas and 17 other states. They argue that when Congress, in 2017, reduced the Sec. 5000A penalty for failure to maintain medical insurance to zero, this action rendered the entire PPACA unconstitutional.

Suspension of personal exemption deduction: The IRS issued proposed regulations in May to clarify that the reduction of the personal exemption to zero does not affect the calculation of the premium tax credit.2 Under the PPACA, the amount of premium tax credit is calculated based on the number of personal exemptions claimed on the taxpayer's individual income tax return. Under the law known as the Tax Cuts and Jobs Act (TCJA),3 for tax years after 2017, the "exemption amount" is zero. The proposed regulations adopt the substance of Notice 2018-84.

Sec. 61: Gross income defined

Fraudulent failure to report business incomeIn the Isaacson4 case, the Tax Court upheld the IRS's determination that a cash-method taxpayer not only underreported his business income but did so with fraudulent intent. The taxpayer, a disbarred attorney and former tax litigation specialist, was determined to have a $2.6 million deficiency and a corresponding $1.9 million civil fraud penalty for omitting from income his 60% contingency fee for services he rendered in 2007.

The taxpayer argued that the 60% contingency fee was not yet his and was held in trust for his clients; however, the court found that he had dominion and control over the funds, and they were held in a personal account and used for his personal enjoyment.

Based on the petitioner's sophistication, education, and prior experience, the court found that he underpaid his income tax with fraudulent intent.

Bank deposits analysis shows underreporting: In Collins,5the Tax Court ruled in the IRS's favor in a case where a tax return preparer underreported his income. When questioned, the taxpayer claimed that the income shown via bank deposits was a cash hoard he and his spouse had saved at home. But based on the IRS's reconstruction of the bank deposits, as well as the number of tax returns processed under his PTIN and firm's EIN and the historical per-return fee cost, the Tax Court found the taxpayer had underreported his income and was subject to civil fraud penalties.

Sec. 67: 2% floor on miscellaneous itemized deductions

In Near,6 married taxpayers claimed they were entitled to deduct certain unreimbursed business expenses on their 2015 federal income tax return (as miscellaneous itemized deductions subject to the 2%-of-adjusted-gross-income floor). The Tax Court rejected their argument, explaining that when employees have a right to reimbursement for expenditures related to their status as employees but fail to claim such reimbursement, the expenses are not deductible as unreimbursed business expenses because they are not "necessary," citing the Ninth Circuit's decision in Orvis.7

Sec. 72: Annuities; certain proceeds of endowment and life insurance contracts

Constitutional challenge to early-withdrawal penaltyIn Conard,8the Tax Court rejected a taxpayer's constitutional challenge to having to pay the 10% additional tax on early distributions received from a qualified retirement plan. She argued, essentially, that the 10% additional tax discriminates against people who are under age 59½, not disabled, and not eligible for any other exception. Unpersuaded by her arguments, the court held that the early-withdrawal penalty did not violate her right under the U.S. Constitution to equal protection under the law.

Sec. 104: Compensation for injuries or sickness

In a private letter ruling,9the IRS found that the amount a taxpayer received in settlement of a lawsuit for personal injury, including emotional distress, was nontaxable.

The taxpayer contracted with a fertility clinic to provide her with a suitable anonymous donor egg and to perform in vitro fertilization. The clinic failed to test the donor egg and embryo that the taxpayer was implanted with, and shortly after birth of the taxpayer's child, genetic testing revealed a specific gene that causes a genetic condition. The genetic condition caused the taxpayer's child to suffer from multiple physical, cognitive, and behavioral disabilities.

The taxpayer sued the fertility clinic on the premise that the clinic's failure to perform the gene test was negligence, making it liable for personal injuries to the child because of the genetic condition and for the taxpayer's emotional distress. The IRS agreed in the letter ruling that the money the taxpayer received in settlement for both the physical injuries and the related emotional distress was excludable from the calculation of gross income (except for amounts that reimbursed the taxpayer for medical expenses that were incurred and previously deducted).

Sec. 108: Income from discharge of indebtedness

Student loan dischargeIn a Tenth Circuit case, Hamilton,10 the court held that a couple were unable to avoid tax on $160,000 of discharged student loans because, in the same year the discharge was granted, they also received a nontaxable partnership distribution of more than $300,000. Even though they moved the partnership distribution funds to a savings account owned by their son to create insolvency, they exercised effective control over the money. The court found that under the substance-over-form doctrine, the money was included in the Hamiltons' assets for determining whether they were insolvent. Because they were solvent after taking that money into account, they were required to pay income tax on the canceled debt.

Student loan discharge safe harbor: The IRS extended its safe-harbor relief from recognizing cancellation-of-debt (COD) income for students whose loans were discharged because their schools were closed or as a result of certain types of fraud.11

Taxpayers within the scope of this revenue procedure will not recognize gross income as a result of the discharge. Also, the IRS will not assert that a creditor must file information returns and furnish payee statements for the discharge of any indebtedness within the scope of the revenue procedure. To avoid creating confusion, the IRS strongly recommends that these creditors not furnish students or the IRS with a Form 1099-C, Cancellation of Debt.

Sec. 131: Certain foster care payments

In Action on Decision 2020-02, the IRS announced that it will acquiesce in Feigh12 in result only. The case concerns the tax treatment of Medicaid waiver payments when determining eligibility for the earned income tax credit (EITC) and the additional child tax credit (ACTC).

The taxpayers, who received Medicaid waiver payments for the care of their adult disabled children in their own home, excluded the payments from gross income but included them in earned income to claim an EITC and an ACTC. Agreeing with the taxpayers, the Tax Court held that even though the IRS (in Notice 2014-7) continues to allow taxpayers to treat such payments as excludable under Sec. 131, the Service cannot reclassify a taxpayer's income through a notice so that it no longer qualifies as earned income for determining eligibility for the EITC or the ACTC.

Sec. 162: Trade or business expenses

Unreimbursed employee expenses: In Near13(also discussed above under Sec. 67), an attorney claimed a deduction for what were deemed to be unreimbursed employee expenses. He reported these expenses on his law practice's Schedule C, Profit or Loss From Business, even though they were related to his employment with the California Department of Transportation (Caltrans). In his Caltrans job, he worked on a civil case outside his home area for approximately two months in 2015, incurring travel-related expenses including lodging. He did not request reimbursement for the travel-related expenses even though Caltrans had an established reimbursement plan for such expenses.

The Tax Court denied the Schedule C expense deduction because these expenses were unreimbursed employee expenses. Also, because the expenses could have been reimbursed, and he was entitled to claim reimbursement, he was denied the opportunity to report them on Form 2106, Employee Business Expenses. The court stated that "employee business expenses paid on behalf of an employer who reimburses such cost may not be converted into trade or business expenses by failure to seek reimbursement."

Travel expenses: In Abubakr,14 the Tax Court held that a taxpayer in the business of making travel arrangements did not have adequate records to support certain deductions for business-related travel expenses. While he claimed a deduction of more than $35,000 for travel expenses he said he paid upfront for his clients, he testified that the clients paid him back for those expenditures. "What seems lacking in substance are alleged expenditures made on behalf of clients which were not paid back," the court noted. The taxpayer reported approximately $94,000 in expenses and $17,000 in gross income on his 2015 Schedule C.

Sec. 163: Interest

In a private letter ruling,15 married taxpayers were granted a 60-day extension (from the date the IRS issued the letter) to elect to treat net capital gains from the disposition of property held for investment as investment income under Secs. 163(d)(1) and (d)(4). The taxpayers based their request to make a late election on Regs. Secs. 301.9100-1 and -3. The IRS found that the taxpayers had acted reasonably and in good faith and that granting the relief would not prejudice the interests of the government.

Sec. 165: Losses

In Staples,16 the Tax Court ruled that a taxpayer could not deduct a loss for anticipated retirement income he had not received. The taxpayer, who retired with a permanent disability under the Federal Retirement Employee System (FERS), was required as a condition of receiving benefits to file for Social Security Disability Income (SSDI). Once SSDI was authorized, his FERS benefits were reduced by a significant percentage. The taxpayer put forth many arguments as to why he should be allowed a loss deduction on account of his FERS benefits' being reduced, including that his SSDI income was earned while in the private sector and his FERS income was earned working in the government sector. Unpersuaded, the court ruled in his case, as it has in many previous cases, that a cash-basis taxpayer cannot deduct unrealized income.

Sec. 170: Charitable, etc., contributions and gifts

Substantiation: In Campbell,17 the Tax Court again dealt with issues related to substantiation required for charitable contributions. In this case, the taxpayers claimed they donated a fractional interest in thousands of new designer eyeglass frames to a Lions Club, but the deduction was denied because of their failure to strictly or substantially comply with the qualified appraisal requirements of Regs. Sec. 1.170A-13(c).

One item to note in this case is that this charitable contribution program was part of an offering memorandum provided to the taxpayers by their tax accountant. Since the tax accountant was a promoter of the program, the taxpayers were unable to claim reliance on the accountant's advice as reasonable cause to avoid penalties. The court deemed that the tax accountant had a conflict of interest and therefore could not be relied upon to avoid penalties. As to the substantiation requirements, the taxpayers failed both the qualified appraisal standard and the contemporaneous written acknowledgment (CWA) requirement.

The appraisal did not meet the tests for a qualified appraisal because it was not an appraisal of what the taxpayers donated. The appraisal was for the entire stock of eyewear that was part of the offering memorandum and not for the specific share of the eyewear that the taxpayers donated. The court determined that the taxpayers were buying and donating a specific number of eyewear frames, not a fractional share, according to the documentation. Thus, the appraisal must be for those specific eyewear frames to be a qualified appraisal. Additionally, the appraisal was not qualified because the description of the property on the appraisal was not of sufficient detail for a person unfamiliar with the property to determine what property was donated, and the appraisal filed with the tax return did not meet that requirement.

As for the CWA, once again the detail on the donation acknowledgment letter is crucial to ensure that the taxpayer is allowed the deduction. Specifically excluded from this letter was necessary language to affirmatively state that no consideration was provided for the contributed property. As the court noted, "this is a mandatory requirement, and no deduction will be allowed if the CWA does not include such a statement."

Conservation easement: In Carter,18 the taxpayers were denied a charitable deduction related to the conveyance by a partnership in which they were partners of an easement that was designed to be a qualified conservation easement. The restricted use of the 500-acre property covered by the easement allowed the development of 11 single-family homes on lots of up to two acres. The Tax Court ruled that the easement was not a qualified real property interest under Sec. 170(h)(2)(C) because it did not meet the perpetual restriction for conservation requirement of Sec. 170(h)(2), since the land on which the homes could be built was not a protected natural habitat of fish and wildlife.

Sec. 172: Net operating loss deduction

Need for concise statement: The decision in Gebman19is a reminder of the importance of complying with the details of the regulations. Regs. Sec. 1.172-1(c) states that a taxpayer claiming a net operating loss (NOL) deduction must file with his or her return "a concise statement setting forth the . . . amount of the [NOL] deduction claimed and all material and pertinent facts relative thereto, including a detailed schedule showing the computation of the . . . [NOL] deduction." This is in accordance with the burden of establishing both the existence of the NOLs for prior years and the NOL amounts that may properly be carried forward to the tax year at issue. Since the taxpayers in this case did not meet that burden, the NOL carryover was not allowed.

Waiving an NOL carryback: In Rev. Proc. 2020-24, the IRS issued guidance about waiving NOL carrybacks. Under the TCJA, beginning in 2018, taxpayers were no longer allowed to carry back NOLs, and thus taxpayers did not need to waive the NOL carryback period if they desired to carry forward an NOL generated in 2018 or 2019. This changed with the Coronavirus Aid, Relief, and Economic Security (CARES) Act,20 which allows taxpayers a five-year carryback of NOLs generated in 2018, 2019, and 2020.

The revenue procedure provides guidance on how to waive an NOL carryback for an NOL arising in a tax year beginning after Dec. 31, 2017, and before Jan. 1, 2020. The election to waive the carryback period for a 2018 or 2019 NOL must be made no later than the due date including extensions for the taxpayer's first tax year ending after March 27, 2020. The taxpayer must attach a separate statement for 2018 or 2019 for which the taxpayer intends to make the election. The election statement must state that the taxpayer is electing to apply Sec. 172(b)(3) under Rev. Proc. 2020-24 and the tax year for which the statement applies. Once made, the election is irrevocable.

Sec. 183: Activities not engaged in for profit

In Den Besten,21 a business breeding and raising cutting horses (for equestrian competition) was deemed to have a profit motive despite years of losses reported on Schedule F, Profit or Loss From Farming, from 2006 to 2010.In addition to the horse activity, the taxpayer had a consistently profitable seed business that he operated as a limited liability company (LLC), reporting that activity on Schedule C for the years in question. In applying the nine factors provided by Regs. Sec. 1.183-2, the Tax Court first found the taxpayer intended to run the horse activity separate from his Schedule C seed business.

Even though the taxpayer did not have a written business plan for the horse activity, the court determined that the taxpayer's overall actions presented evidence of his profit objective for the horse business, which included the breeding of, and the ultimate training of, two horses that became world champion cutting horses. His actions demonstrated the expertise that he had in this specific activity, along with the overall time devoted to this activity and the expectation that the business's assets would appreciate in value as world champion horses.

The taxpayer maintained only canceled checks and bank statements, along with a yearly summary that was provided to his CPA for tax return preparation; however, the court found that the taxpayer maintained the necessary books and records for his business activity. The court even stated that "in the agricultural business it is not unusual to see no maintenance of records other than canceled checks and deposit slips." Additionally, the court found a profit motive in the fact that the taxpayer sold merchandise with his own unique brand at national cutting horse events that he would attend, along with purchasing advertisements for his business in cutting-horse-related programs and catalogs.

In addition, the taxpayer's entrepreneurial skills and determination to succeed were demonstrated by his successful seed business, and the court noted that the "potential consumer audience in the agricultural setting is substantially similar." Finally, regarding the elements of personal pleasure and recreation from the activity, the court concluded that "[w]hile he surely derived personal pleasure from the recreational aspects of the cutting horse activity, his efforts went well beyond the leisurely aspects of horseback riding or the routine tasks of caring for horses."

Sec. 212: Expenses for production of income

The Tax Court ruled in Onyeani22 that the taxpayer was not entitled to deduct $61,500 for payments to attorneys in connection with tax litigation involving a "termination assessment" that the IRS made after he attempted to wire money to a foreign bank. The taxpayer argued that the deduction was allowable under Sec. 212(3), which permits a deduction for expenses paid "in connection with the determination, collection, or refund of any tax." Disagreeing, the court disallowed these expenses because the cash-basis taxpayer could not prove the legal fees were directly connected with the litigation and were paid in 2015, the year claimed.

Sec. 265: Expenses and interest relating to tax-exempt income

In Notice 2020-32, the IRS ruled that amounts forgiven under a Paycheck Protection Program (PPP) loan that are used to pay qualified expenses are not also deductible as expenses on the taxpayer's 2020 income tax return. As a rationale for denying these expense deductions, the IRS cited Sec. 265, which limits deductions attributable to tax-exempt income.

Sec. 280A: Disallowance of certain expenses in connection with business use of home, rental of vacation homes, etc.

In Collins23 (also discussed above under Sec. 61), the husband's Schedule C included a home office deduction for the rental of the basement in the home he shared with his wife, who was the owner. Because the husband used the entire basement for tax return preparation and for personal endeavors, and there was no evidence fair rental value was paid for the space he rented, the Tax Court denied the deduction.

Sec. 401: Qualified pension, profit-sharing, and stock bonus plans

The Setting Every Community Up for Retirement Enhancement (SECURE) Act of 2019,24 enacted in December 2019, was designed primarily to encourage retirement savings but also contained an important, taxpayer-unfriendly provision that affects estate planning: Most beneficiaries of IRAs and qualified plans must withdraw all money from inherited accounts within 10 years. Prior law provided more flexibility because beneficiaries were usually allowed to withdraw inherited amounts from a tax-favored account or plan over the beneficiary's lifetime. The new 10-year limit applies generally with respect to plan participants or IRA owners who die after Dec. 31, 2019. Certain beneficiaries are exempt from the new rule: surviving spouses, minor children, chronically ill individuals, and individuals within 10 years of the deceased person's age (see Sec. 401(a)(9)).

The SECURE Act's other provisions were mostly taxpayer-friendly. Among other things, the act:

  • Repealed the maximum age for contributing to a traditional IRA, so that traditional IRAs are now treated the same as Roth IRAs and employer-sponsored plans, which have no age limit (relatedly, the act reduces the amount of charitable IRA distributions allowed to taxpayers over 70½ — by the aggregate IRA contribution deductions allowed to them after they turn 70½ — but does not raise the age requirement to make those charitable distributions);
  • Increased the age after which required minimum distributions from certain retirement accounts must begin to 72 (from 70½);
  • Provided that withdrawals for birth or adoption are exempt from the 10% additional tax on early distributions;
  • Expanded eligibility rules to enable more long-term, part-time employees to participate in retirement plans; and
  • Made it easier for certain home health care workers (who receive Sec. 131 difficulty-of-care payments) and graduate and postdoctoral students (who receive stipends, fellowships, and similar payments) to make retirement contributions by modifying what counts as compensation for purposes of determining contribution limits.

Sec. 461: Excess business losses

The CARES Act temporarily suspended the Sec. 461(l) limitation on excess business losses for passthrough businesses and sole proprietorships for the 2018, 2019, and 2020 tax years.25 This effectively extended NOL relief to partnerships and sole proprietors. Further, the CARES Act made certain technical corrections to Sec. 461(l), including a change to Sec. 461(l)(2), allowing carryover losses into subsequent tax years.

When the temporary suspension ends and Sec. 461(l) comes into effect in 2021, the rules will be different. In 2021 and after, wages are no longer considered business income, and business capital losses are not taken into account in the calculation, whereas net business capital gains are taken into account. For some taxpayers, these revised calculation rules will be beneficial; for others, they will not be. But these revisions appear to track the original farm loss rules that Sec. 461(l) was supposed to replicate when enacted in the TCJA.

Sec. 469: Real estate professional status

In two cases, the IRS prevailed over taxpayers' claims of real estate professional status, which requires a person to spend more than 50% of his or her personal service hours and more than 750 hours actively working in the business of real estate.

Vague evidence: In Hakkak,26 an attorney claimed real estate professional status for his commercial rental properties and for his interests in rentals held in five LLCs for the years under examination of 2011-2012, but the Tax Court ultimately sided with the IRS. The attorney, a California resident whose properties were located in California and Texas, reported his business income on Schedule C for his non-personal injury law work and through an S corporation for his personal injury law work. He was paid on a Form W-2, Wage and Tax Statement, from the S corporation.

The IRS found, and the court agreed, that his records failed to support real estate professional status. At trial, the taxpayer presented extensive evidence, including testimony from witnesses and handwritten calendars, to support his claim that he was a real estate professional. However, the court found that the evidence was vague and lacking in specificity, and was not trustworthy. Thus, it concluded that the taxpayer failed to meet the requirements set forth in Sec. 469(c)(7)(B) for the years at issue.

Substantiation: In a Ninth Circuit case, Simonelli,27 the court upheld the Tax Court's findings that a taxpayer did not meet the requirements for real estate professional status because she did not substantiate that she spent more than 750 hours actively working in the business of real estate. The court denied rental losses for the years 2011-2012.

Election to treat all interests in rental real estate as single rental real estate activityIn two private letter rulings,28 the IRS granted taxpayers 120-day extensions (from the date of the letter ruling) to make a Sec. 469(c)(7)(A) election to treat all their interests in rental real estate as a single rental real estate activity. In both cases, the taxpayers did not make the election because they were not advised by their return preparer of its availability. Regs. Sec. 301.9100-3(b) provides that where a taxpayer reasonably relied on a qualified tax professional, including a tax professional employed by the taxpayer, and the tax professional failed to make or advise the taxpayer to make the election, the taxpayer will generally be deemed to have acted reasonably and in good faith.

Sec. 1012: Basis of property — cost

In Manroe,29 the Tax Court ruled it lacked jurisdiction to consider penalties (related to outside bases) determined at the partnership level that the married taxpayers sought to challenge.

The taxpayers had participated in a son-of-boss tax shelter transaction involving an entity known as BLAK Investments (BLAK). The transaction involved the contributions of offsetting positions (proceeds of short sales of U.S. Treasury notes on one side of the scale, and short positions on Treasury notes on the other side). BLAK later redeemed their respective partnership interests. The court noted that since BLAK was a sham and was disregarded for federal tax purposes, the taxpayers are treated as holding BLAK's assets directly, and their adjusted bases in the assets are determined under Sec. 1012(a). The court noted that partner-level determinations were needed to determine their outside bases in their sham partnership.

Sec. 1016: Adjustments to basis

In Rev. Rul. 2020-5, issued in February 2020, the IRS clarified how to calculate the income recognized upon the sale of life insurance contracts. The guidance was needed because the TCJA amended Sec. 1016(a) to provide that, in determining the basis of a life insurance contract or an annuity contract, no adjustment is made for mortality, expense, or other reasonable charges incurred under the contract.

The revenue ruling reexamined Situations 2 and 3 of Rev. Rul. 2009-13 and Situation 2 of Rev. Rul. 2019-14. The Service stated that the analysis and holdings relating to A's adjusted basis in these three situations in the prior revenue rulings are inconsistent with the current language of Sec. 1016(a)(1)(B). Under Sec. 1016(a)(1)(B), the cost basis of a life insurance contract is not reduced by the cost of insurance without regard to why the contract was purchased. Therefore, the Service modified Rev. Rul. 2009-13 and Rev. Rul. 2009-14 to the extent they are inconsistent with the rule set forth in Sec. 1016(a)(1)(B). This revenue ruling is effective for transactions entered into on or after Aug. 26, 2009.

Sec. 1031: Exchange of real property held for productive use or investment

The Tax Court in Gluck30agreed with the IRS's determination that the replacement property identified in a Sec. 1031 exchange was an interest in a partnership for which like-kind exchange treatment did not apply under Sec. 1031(a)(2)(D) (as in effect for 2012). The taxpayers sold a condominium unit in 2012 and designated a purported 25% interest in the partnership Greenberg & Portnoy (G&P) as the replacement property. G&P held a rental apartment building. The court concluded that the taxpayers' entitlement to Sec. 1031 treatment is not a "factual affected item" but rather is a "computational affected item" exempt from deficiency procedures.

The court also agreed with the IRS that the accuracy-related penalty determined was within its deficiency jurisdiction because there was no adjustment to any partnership item that would exclude the penalty from deficiency procedures under Sec. 6230(a)(2)(A)(i). The court noted that the taxpayer's claim for "like-kind exchange treatment [was] 100% inconsistent with the treatment of [the] partnership items on G&P's return" and the IRS had simply adjusted the taxpayers' tax liability to properly reflect treatment of a TEFRA partnership item.

Sec. 1222: Other terms relating to capital gains and losses

The U.S. District Court for the Eastern District of Louisiana ruled against married taxpayers in Goldring,31 holding that an amount they received in settlement of a securities lawsuit was not a gain from the sale of a capital asset but rather gross income under Sec. 61.

The case arose out of a merger involving a company in which the wife held stock. Unhappy with the price per share she was to receive for her stock under the cash-out merger, she filed a petition with the Delaware Court of Chancery requesting an appraisal of the fair value of her shares. After the Delaware court determined a per-share value higher than the merger price, the parties reached a settlement. The taxpayers contended that the entire settlement amount should be treated as payment in exchange for a capital asset. Disputing this, the IRS argued that the portion of the settlement that represented interest paid to compensate her for the loss of use of her stock while the case was being litigated (more than $26 million) should be taxed as ordinary income. The district court agreed with the IRS, concluding that the amount in question was not tied to the value of the stock at issue because it reflected statutory interest and not a gain from the sale of a capital asset.

Secs. 1401 and 6654: Deferral of portion of self-employment tax

The CARES Act allows self-employed taxpayers to delay payment of one-half of their estimated self-employment tax imposed under Sec. 1401(a) (Social Security tax) during the "payroll tax deferral period" ending Jan. 1, 2021.32 In accordance with the act, one-half of any delayed payments will be due Dec. 31, 2021, and the second half due Dec. 31, 2022. For any tax year that includes any part of the payroll tax deferral period, 50% of the Social Security tax imposed on net earnings from self-employment during that payroll tax deferral period is not used to calculate the installments of estimated tax due under Sec. 6654.

As originally enacted in March, the CARES Act provided that businesses would lose eligibility to defer Social Security tax once they took advantage of loan forgiveness under the Paycheck Protection Program, but that prohibition was repealed in June.33


1Patient Protection and Affordable Care Act, P.L. 111-148; California v. Texas, No. 19-840 (U.S. 3/2/20) (petition for certiorari granted).


3P.L. 115-97.

4Isaacson, T.C. Memo. 2020-17.

5Collins, T.C. Memo. 2020-50.

6Near, T.C. Memo. 2020-10.

7Orvis,788 F.2d 1406, 1408 (9th Cir. 1986).

8Conard, 154 T.C. No. 6 (2020).

9IRS Letter Ruling 201950004.

10Hamilton, No. 19-9000 (10th Cir. 4/7/20).

11Rev. Proc. 2020-11.

12Feigh, 152 T.C. No. 15 (2019).

13Near, T.C. Memo. 2020-10.

14Abubakr, T.C. Summ. 2020-8.

15IRS Letter Ruling 202020015.

16Staples, T.C. Memo. 2020-34.

17Campbell, T.C. Memo. 2020-41.

18Carter, T.C. Memo. 2020-21.

19Gebman, T.C. Memo. 2020-1.

20Coronavirus Aid, Relief, and Economic Security Act, P.L. 116-136.

21Den Besten, T.C. Memo. 2019-154.

22Onyeani, T.C. Memo. 2020-15.

23Collins, T.C. Memo. 2020-50.

24Setting Every Community Up for Retirement Enhancement Act, P.L. 116-94.

25Section 2304 of the CARES Act.

26Hakkak, T.C. Memo. 2020-46.

27Simonelli, 790 Fed. Appx. 870 (9th Cir. 2020), aff'g T.C. Memo. 2017-188.

28IRS Letter Rulings 202006010 and 202006012.

29Manroe, T.C. Memo. 2020-16.

30Gluck, T.C. Memo. 2020-66.

31Goldring, No. 18-10756 (E.D. La. 4/13/20).

32Section 2302(b)(2) of the CARES Act.

33Paycheck Protection Program Flexibility Act of 2020, P.L. 116-142, §4.

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