Table of Contents introduction & vocabulary 2


Transactions Involving Borrowed Funds



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Transactions Involving Borrowed Funds


  • Code § 61(a)(12). “If [a] debt is subsequently cancelled for less than its face value, [the taxpayer] is considered to have income.”

  • Code § 65. Ordinary loss defined.

  • Code § 108(a). Income from discharge of indebtedness—Exclusion from gross income.

  • Code § 108(b). Income from discharge of indebtedness—Reduction of tax attributes.

  • Code § 108(d)(1). Income from discharge of indebtedness—Meaning of terms; special rules relating to certain provisions—Indebtedness of taxpayer.

  • Code § 108(d)(2). Income from discharge of indebtedness—Meaning of terms; special rules relating to certain provisions—Title 11 case.

  • Code § 108(d)(3). Income from discharge of indebtedness—Meaning of terms; special rules relating to certain provisions—Insolvent.

  • Code § 108(e). Income from discharge of indebtedness—General rules for discharge of indebtedness (including discharges not in Title 11 cases or insolvency)

  • Code § 108(f). Income from discharge of indebtedness—Student loans.

  • Code § 165(c). Losses—Limitation on losses of individuals.

  • Code § 165(d). Losses—Wagering losses.

  • Code § 6321. Lien for taxes.

  • Regulation § 1.61-12(a). Income from discharge of indebtedness—In general.

No gain on loan—no loss on lending—gains (for lender) on interest payments—gains (for borrower) on cancelled debt

    • Tax benefit—don’t initially include debt as income b/c they intended to pay it back—once they don’t intend to pay it back  taxable

Collins v Commissioner—1993

Off-track Betting parlor—drafted up tickets worth $80,280—at the end of the day was behind $32,105—at the end of the day had tickets worth $48,000 (same day restitution)



All unlawful gains are taxable  taxable income = $80,280 (“Collins took illegally acquired assets and spent them unwisely”)—can only deduct gambling losses against his winnings—taxed for the benefit he derived from stealing

  • Why isn’t this excludable as borrowing?

    • No mutuality of intent to repay the loan

    • James v United States—unlawful gains taxable—test: mutual intent and consensual recognition

  • What is the authority for deducting $42,000?

    • § 165(c)—Limitation on losses of individuals

    • Can he deduct the $38,000 loss?

      • Could he call it a transaction entered into for profit? A transaction is 1-sided, but generally a good argument

      • Unlikely to make money, irrational to expect to profit  IRS could argue that gambling is not an enterprise where one could expect to make profit

        • i.e. stealing to use for personal gains? If Avi stole cash from Ben and used the money to buy a car he could NOT deduct the car but he COULD deduct the restitution

    • § 165(c)(3)—can deduct gambling losses

  • § 165(d)—just within gambling transactions you can net your gambling position against your game




    Scenario 1

    Scenario 2

    Amount Stolen

    $80

    $80

    Round 1







    Winnings/Losses

    ($38)

    $10

    Round 2







    Winning/Losses




    ($48)

    Net Gambling Position

    ($38)

    ($38)

    Deduction

    $0

    $0

    Total Gross Income

    $80

    $80

  • Does this seem harsh that he’s being taxed on all $80,000?

    • No—someone else who was able to gamble with $80,000 would be taxed on that income

    • Doesn’t measure his ability to pay—but punitive value

  • What is the policy of making people include stolen funds in income? (J. Blackmun’s dissent in Rutkin)

    • § 6321—IRS gets a lien—gets priority over victim’s restitution

James Test—stealing or borrowing?

What is the James test exactly? “consensual recognition, express or implied, of the obligation to repay”

“Without restriction on the disposition”—why is this here? Illiquid—can only use for specified purpose—James refers to taxable income, not nontaxable—if car dealership sells you a car for $30,000 then says you only have to repay $7,000 don’t have to pay $23,000 forgiven debt—we’ll come back to this later

Gilbert v Commissioner

Gilbert acquired a bunch of Celotex (his employer) stock on margin—had the corporation pay for the stock—Board didn’t approve the borrowing from the company



  • Similar to Collins but because he has authority he can argue that he was going to pay Celotex back

Problem Set #6: Transactions Involving Borrowed Funds

  1. Rob borrows $1,000 from the bank and spends it. Is the money he borrows income? When Rob repays the loan, can he deduct the $1,000 he repays? (Ignore, for now, the question of whether the interest Rob pays on the loan is deductible.)

§ 61—can’t be income b/c he intends to repay—no income  no deduction—increase in assets offset by increase in liability

Collins is the best authority for this (no Code section) if the borrower pays business interest they get to deduct it, lender realizes income from interest § 61

  1. Suppose David Zarin, the compulsive gambler, finds himself back in a casino and sitting next to someone who is very drunk and has a large pile of gambling chips. What are the tax consequences if:

  1. Zarin simply takes chips worth $200,000 from this fellow gambler without anyone suspecting anything and loses them all gambling?

Taxable income = $200,000 under James (“all unlawful gains are taxable”)

  1. Zarin takes the $200,000 of chips but says to the drunk gambler, “Don’t worry. If I win, I’ll pay you back.” He then loses all of them.

Probably still taxable—not a “mutual understanding between the borrower and the lender of the obligation to repay and a bona fide intent on the borrower’s part to repay the acquired funds”

Can he reasonably expect that he will win? No intention to repay if he lost  taxable like (a)



  1. Same as (b) except that Zarin wins $280,000. He returns the $200,000 of chips to the drunk gambler and pockets $80,000. Would it make any difference if he hit the jackpot at 11:55pm on New Year’s Eve and replaced the chips at 1:00am on New Year’s Day?

Loan: actual repayment indicates mutual understanding of obligation  taxable income = $80,000

OR (more consistent) still unlawful gains, not loan  taxable income = $280,000 w/ deduction for $200,00 repayment



§ 165(c)—restitution only counts in the same year—if the stealing and the repayment come on New Years Eve and New Years Day he’ll lose out—forced to take deduction in the future (TVM)—may not be able to use entire deduction against gambling losses—could be in a different tax bracket

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