EPISODE · Dec 23, 2025 · 22 MIN
Why that holiday “thank you” might be taxable
from The Death Readiness Podcast: Not your dad’s estate planning podcast · host Jill Mastroianni
What You’ll Learn in This EpisodeWhy gifts in the context of work relationships are generally taxable income to the recipient, even when labeled as “holiday gifts”The key difference between gifting to family (federal gift tax rules) and gifting in an employment or business context (income tax rules)Why holiday cash gifts do not qualify as de minimis fringe benefits, and why gift cards are treated as cash equivalentsWhat employee achievement awards are, why cash doesn’t qualify, and how strict the requirements really are, including dollar limits and “meaningful presentation” rulesHow gifts to someone who is both family and employee are analyzed, and why intent and context matter more than labelsWhy gifts tied to service, loyalty, or length of employment are treated as compensation, even when they feel heartfeltHow the Supreme Court’s decision in Commissioner v. Duberstein (1960) still governs whether a transfer is a true gift or taxable incomeWhat can happen in estate planning when bequests to employees are framed as thanks for service—and how wording can change tax outcomes for beneficiariesResources & LinksEpisode 46: How to Give Money Without Triggering Gift TaxCommissioner v. Duberstein, 363 U.S. 278 (1960)The Supreme Court case that established the “detached and disinterested generosity” test for gifts connected to business or employment relationshipsThe Death Readiness Playbook - A practical, guided system for organizing information, making decisions, and turning good intentions into real clarity www.deathreadiness.com/playbookSee Internal Revenue Code Sections below.Connect with Jill:Website: DeathReadiness.comEmail: [email protected] more about Jill’s solutionsSubscribe to the Death Readiness Dispatch!Submit a question for Tuesday TriageDid you enjoy this episode? Share it with someone you care about.Internal Revenue Code Sections26 U.S. Code § 102(a) General rule. Gross income does not include the value of property acquired by gift, bequest, devise, or inheritance.26 U.S. Code § 102(c) Employee gifts(1) In generalSubsection (a) shall not exclude from gross income any amount transferred by or for an employer to, or for the benefit of, an employee.(2) Cross referencesFor provisions excluding certain employee achievement awards from gross income, see section 74(c).For provisions excluding certain de minimis fringes from gross income, see section 132(e).26 U.S. Code §274(j) Employee achievement awards(1) General ruleNo deduction shall be allowed under section 162 or section 212 for the cost of an employee achievement award except to the extent that such cost does not exceed the deduction limitations of paragraph (2).(2) Deduction limitationsThe deduction for the cost of an employee achievement award made by an employer to an employee—(A) which is not a qualified plan award, when added to the cost to the employer for all other employee achievement awards made to such employee during the taxable year which are not qualified plan awards, shall not exceed $400, and(B) which is a qualified plan award, when added to the cost to the employer for all other employee achievement awards made to such employee during the taxable year (including employee achievement awards which are not qualified plan awards), shall not exceed $1,600.(3) DefinitionsFor purposes of this subsection—(A) Employee achievement award(i) In generalThe term “employee achievement award” means an item of tangible personal property which is—(I) transferred by an employer to an employee for length of service achievement or safety achievement,(II) awarded as part of a meaningful presentation, and(III) awarded under conditions and circumstances that do not create a significant likelihood of the payment of disguised compensation.(ii) Tangible personal propertyFor purposes of clause (i), the term “tangible personal property” shall not include—(I) cash, cash equivalents, gift cards, gift coupons, or gift certificates (other than arrangements conferring only the right to select and receive tangible personal property from a limited array of such items pre-selected or pre-approved by the employer), or(II) vacations, meals, lodging, tickets to theater or sporting events, stocks, bonds, other securities, and other similar items.26 U.S. Code §74(c) Exception for certain employee achievement awards(1) In generalGross income shall not include the value of an employee achievement award (as defined in section 274(j)) received by the taxpayer if the cost to the employer of the employee achievement award does not exceed the amount allowable as a deduction to the employer for the cost of the employee achievement award.(2) Excess deduction award. If the cost to the employer of the employee achievement award received by the taxpayer exceeds the amount allowable as a deduction to the employer, then gross income includes the greater of—(A) an amount equal to the portion of the cost to the employer of the award that is not allowable as a deduction to the employer (but not in excess of the value of the award), or(B) the amount by which the value of the award exceeds the amount allowable as a deduction to the employer.The remaining portion of the value of such award shall not be included in the gross income of the recipient.(3) Treatment of tax-exempt employers. In the case of an employer exempt from taxation under this subtitle, any reference in this subsection to the amount allowable as a deduction to the employer shall be treated as a reference to the amount which would be allowable as a deduction to the employer if the employer were not exempt from taxation under this subtitle.(4) Cross reference. For provisions excluding certain de minimis fringes from gross income, see section 132(e). This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy. Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents. Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
NOW PLAYING
Why that holiday “thank you” might be taxable
No transcript for this episode yet
Similar Episodes
Mar 26, 2026 ·1m
Mar 19, 2026 ·34m
Feb 18, 2026 ·11m
Feb 11, 2026 ·45m