## Facts

- Milton Peebles discovered his wife was having an affair with a local physician, Dr. John Hestir, and gathered evidence of the affair.
- Peebles confronted Hestir, demanded $150,000, and threatened to sue if Hestir did not pay.
- After Peebles compelled his wife to disclose the affair to Hestir’s wife, Hestir agreed to pay Peebles $25,000.
- During the exchange, Hestir described the payment as “free money” but cautioned that the IRS would likely treat it as taxable.
- Peebles agreed that, if he later divorced, he would not name Hestir in the divorce proceedings.
- Peebles later complained to the Arkansas State Medical Board about Hestir’s conduct; Hestir admitted the affair and expressed remorse to the Board.
- Hestir reported the $25,000 payment on his own tax return; Peebles did not include it in his gross income, claiming it was a gift.
- The IRS determined a deficiency based on inclusion of the $25,000 in Peebles’s gross income; Peebles petitioned the Tax Court for redetermination.

## Issues

1. Whether the $25,000 payment qualified as a “gift” excludable from gross income under I.R.C. § 102(a).
2. Whether the payment was includible in gross income under I.R.C. § 61(a) because it was made in exchange for settlement of threatened claims and/or forbearance.

## Decision

- The Tax Court held the $25,000 payment was not a gift under I.R.C. § 102(a).
- The court concluded the payment was includible in Peebles’s gross income under I.R.C. § 61(a).
- Judgment was entered for the Commissioner, sustaining the deficiency attributable to the omitted $25,000 (subject to any computational adjustments).

## Legal Principles

- Gross income under I.R.C. § 61(a) is broadly defined and includes amounts received unless a specific statutory exclusion applies.
- The gift exclusion in I.R.C. § 102(a) depends on the transferor’s dominant intent; a transfer is a gift only if motivated by “detached and disinterested generosity,” not by anticipated benefit, obligation, or bargaining.
- Payments made to settle or avoid threatened legal action, or to obtain a promise of forbearance (e.g., not suing or not naming a person in related litigation), are generally treated as consideration to the recipient rather than as gifts.
- Labels attached to a transfer (such as “free money” or references to conscience or remorse) do not control; the surrounding circumstances determine tax characterization.

## Conclusion

The Tax Court treated the $25,000 as taxable income because the circumstances showed it was a negotiated payment tied to threatened litigation and Peebles’s agreement to forgo actions adverse to the payor, not a gratuitous transfer made from detached generosity.


Peebles v. Comm'r, T.C. Summ. Op. 2006-61 (2006)