INSURANCE COMMON TRAPS THAT YOU SHOULD KNOW ABOUT...

Billion Dollar Law & Tax Mistakes

Here are 101 cases that cover a range of business succession, intellectual property, estate planning, and advanced estate and tax planning strategies... that went wrong!!!

The goal: Learn from someone else's mistakes so you don't have to make them, and your family does not have to face the consequences of your mistakes


BUSINESS SUCCESSION MISTAKES, MYTHS, GAPS, AND TRAPS THAT CAN ERODE YOUR LIFE'S WORK...

  1. Myth #1: The Giustina Case: Why Your LLC Is a Roadblock, Not a Shield, Against Probate (IRC §2033)

  2. Myth #2: The Strangi Case: You Transferred Your Business to a Trust, But the IRS Still 'Clawed It Back' (IRC §2036)

  3. Myth #3: The True v. Commissioner Case: Why a "Dusty" Buy-Sell Agreement Won't Save You from the IRS (IRC §2703)

  4. Myth #4: The Maggos Case: Your "Freeze" Technique Backfired—Here's Why (IRC §§2036, 2038)

  5. Myth #5: The Eddy Case: A Missed 9-Month Deadline Cost This Estate Millions in Taxes (IRC §2032)

  6. Myth #6: The Anderson Case: Why a Lack of Valuation Can Cost an Estate Millions (IRC §2031(b))

  7. Myth #7: Your Will Is a Map to Probate, Not a Way to Avoid It (UPC §3-101)

  8. Myth #8: The Family Business Case: Your Family Has No Authority to Run Your Business Without This Document (UPC §3-307)

  9. Myth #9: The ILIT Audit: How Your "Tax-Free" Life Insurance Could Still Be Taxed (IRC §2042)

  10. Myth #10: The Church & Giselman Cases: The IRS Knows About Your Gifts, Even If You Didn't File the Paperwork (IRC §2511)

  11. Myth #11: The Steinberg Case: An Improperly Structured LLC Can Lead to Probate (UPC §2-101)

  12. Myth #12: The Dorn Case: Your "Phantom Equity" Isn't Invisible to the IRS (IRC §§2036, 2038)

  13. Myth #13: The Robinson Case: Procrastinating on Your Valuation Cost an Estate Millions (IRC §§2031, 2032)

  14. Myth #14: The Church v. U.S. Case: Gifting Property, Not Just Cash, Can Trigger Tax Penalties (IRC §2511)

  15. Myth #15: The Littick v. Comm. Case: An Internal Price Agreement Won't Fool the IRS (IRC §2703)

  16. Myth #16: The Klauss Case: The IRS Can Reject Your Valuation and Apply Its Own (IRC §2031)

  17. Myth #17: The True v. Commissioner Case: Why a "Dusty Document" Is Worthless in an Audit (IRC §2703)

  18. Myth #18: The Maxine Robinson v. Comm. Case: A Missing "Death Clause" Caused a Valuation Dispute (UPC §2-101)

  19. Myth #19: The S-Corp Case: How a Will Can Accidentally Cause Your S-Corp to Lose Its Tax Status (IRC §1361(b) (1) (B))

  20. Myth #20: The Thompson v. Comm. Case: Registering IP in an LLC Doesn't Protect It from Estate Tax (IRC §§2036, 2038)

  21. Myth #21: The Joint Bank Account Case: Joint Accounts Don't Grant Legal Control of a Business (Uniform Probate Code)

  22. Myth #22: The IRS v. Coinbase Case: Your Crypto Is Trackable, Taxable, and Easily Lost Forever (IRC §2031)

  23. Myth #23: The Estate of German Case: Your Revocable Trust Avoids Probate, But Not Estate Tax (IRC §2038)

  24. Myth #24: The Estate of Gallo Case: No Plan Means Family Fights That Cost Millions in Legal Fees (UPC §3-112, IRC §2031)

  25. Myth #25: The Estate of Linton Case: The IRS Will Tax a Paper-Only Gift (IRC §2511)

  26. Myth #26: The Estate of Wheeler Case: Deathbed Transfers Are a Red Flag for the IRS (IRC §2035(a))

  27. Myth #27: The Estate of Powell Case: Serving as a Trustee of Your Own Irrevocable Trust Puts Your Assets at Risk (IRC §§2036, 2038)

  28. Myth #28: The S-Corp Case: A Will Can't Transfer S-Corp Shares to Just Anyone (IRC §1361)

  29. Myth #29: The Hackl v. Commissioner Case: Don't Assume Your Gifts Are Under the Exclusion Limit (IRC §2503(b))


    INTELLECTUAL PROPERTY THAT WAS DESTROYED AND DILUTED DUE TO POOR PLANNING...

  30. Myth #30: The Thompson v. Comm. Case: Your "Personal" IP Is Part of Your Taxable Estate (IRC §2031)

  31. Myth #31: The Steinberg v. U.S. Case: Registering Your IP Is Just Step One to Avoiding Estate Tax (IRC §2031)

  32. Myth #32: The Estate of Prince Case: A Lack of Planning Can Freeze Your IP Rights and Royalties for Decades (IRC §2033)

  33. Myth #33: The Thompson v. Commissioner Case: Your Personally Owned Patent Isn't Licensed to Your Business by Default (IRC §2036)

  34. Myth #34: The Powell v. Commissioner Case: An LLC Won't Protect Your IP If You Retain Control (IRC §2038)

  35. Myth #35: The Estate of German Case: Your Revocable Trust Won't Remove IP Value from Your Estate (IRC §2038)

  36. Myth #36: The Michael Jackson Estate Case: Don't Underestimate the Value of Your IP (IRC §2031)

  37. Myth #37: The Estate of Cecil v. Commissioner Case: The IRS Will Assign a Value to Your Trademark (IRC §2031(b))

  38. Myth #38: The Estate of Steinberg Case: The IRS Can Include Future Royalties in Your Estate's Valuation (IRC §§2031, 691)

  39. Myth #39: The Church v. U.S. Case: Informal Gifts of IP Are Ignored by the IRS (IRC §2511, §2701)

  40. Myth #40: The Whitney Houston Estate Case: Intangible IP is Not Safe from Estate Tax (IRC §2031)

  41. Myth #41: The Aretha Franklin Case: How a Handwritten Will Led to Chaos Over an $80M Estate

  42. Myth #42: The King of Random Case: A Digital Empire Can Be Lost Without a Trust

  43. Myth #43: Your Will Won't Protect a Real Estate Business from Probate

  44. Myth #44: The Thompson Case: Your Personal Brand Can Get Stuck in Probate, Freezing Ad Revenue

  45. Myth #45: The Bob Marley Estate: Why a Lack of a Will Led to Decades of Legal Battles Over a Multi-Million Dollar Estate

  46. Myth #46: The Jimi Hendrix Estate: Planning Isn't Just for Large Estates

  47. Myth #47: The Heath Ledger Estate: How Outdated Documents Can Result in Poor Asset Distribution

  48. Myth #48: The Robin Williams Case: Your Name and Likeness Are Property That Must Be Assigned

  49. Myth #49: The Amy Winehouse Case: Why Delaying Estate Planning Is the Enemy of Your Legacy

  50. Myth #50: The Philip Seymour Hoffman Case: Why Outdated Documents Can Be as Bad as Having No Documents at All

    LIFE INSURANCE MISTAKES AND TRAPS THAT DILUTE YOUR "INSURANCE POLICIES"

  51. Myth #51: The Estate of Kurihara Case: Retaining Control Over a Life Insurance Policy Triggers Estate Inclusion (IRC §2042(c))

  52. Myth #52: The Estate of Becker Case: The 3-Year "Look-Back" Rule Is Real and Can't Be Ignored (IRC §2035(a))

  53. Myth #53: The Kurihara Case: Paying Premiums for an ILIT from a Personal Account is a Red Flag for the IRS (Treas. Reg. §20.2042-1(c)(2))

  54. Myth #54: The ILIT Trustee Case: Serving as Your Own Trustee Is a "Red Flag" for the IRS (Treas. Reg. §20.2042-1(c)(2))

  55. Myth #55: The Corporate Policy Case: Why a Policy Owned by Your Corporation Still Counts in Your Estate (IRC §§2036, 2038)

  56. Myth #56: The Crummey Case: Waivers Are Not Enough—Beneficiaries Must Have a Real Withdrawal Right (IRC §2503(b))

  57. Myth #57: The Whole-Life Policy Case: Your Policy's Cash Value Can Trigger Estate Inclusion (Treas. Reg. §20.2042-1(c)(2))

  58. Myth #58: The Spouse Case: Paying Premiums for a Spouse-Owned Policy Still Counts (IRC §2042)

  59. Myth #59: The Split-Dollar Case: Retaining Any Right to a Loan or Dividend Can Kill Your Plan (Treas. Reg. §20.2042-1(c)(2))

  60. Myth #60: The Physician Case: Even Small Policies Can Push Your Estate Over Tax Thresholds (IRC §2042)

  61. Myth #61: The Levine Case: A Split-Dollar Arrangement Can Still Trigger Estate Inclusion (IRC §§2036, 2038)

  62. Myth #62: The Connelly v. United States Case: The Supreme Court Just Ruled That Corporate-Owned Insurance Can Be Included in Your Estate (IRC §§2036, 2038, 2703)

  63. Myth #63: The Estate of Levine Case: The IRS Taxes the Entire Benefit Stream of a Split-Dollar Deal, Not Just the Receivable (IRC §§2036, 2038, 2042, 2703)

  64. Myth #64: The Kurihara Case: The Timing of Your Transfer Can Overrule the Formal Documents (IRC §2035(a))

  65. Myth #65: The Kurihara Case: The IRS Can Attribute a Trustee's Actions to You (Treas. Reg. §20.2042-1(c)(2))

  66. Myth #66: The Levine Case: How the IRS Disregarded a Trust and Taxed a Split-Dollar Receivable (Treas. Reg. §1.61-22, IRC §§2036, 2038, 2703)

  67. Myth #67: An ILIT Modification Can Resurrect a Dead Tax Problem (IRC §§2035(a), 2038)

  68. Myth #68: The Kurihara Case: Retaining the Power to Change Beneficiaries Is a Red Flag for the IRS (Reg. §20.2042-1(c)(2))

  69. Myth #69: Heirs Paid Tax on "Income in Respect of a Decedent" (IRC §691)

  70. Myth #70: The Connelly v. United States Case: How One Policy Can Trigger Multiple Tax Penalties (IRC §§2036, 2038, 2042)

    HIGH-VALUE INVESTMENTS, DIGITAL ASSETS, STOCKS, AND ESTATE PLANNING MISTAKES

  71. Myth #71: U.S. v. Estate of German Case: A Revocable Trust Avoids Probate, But Not Estate Tax (IRC §2038)

  72. Myth #72: The Estate of Fick Case: A Will Is a Roadmap to Probate, Not a Way to Avoid It (UPC §2-502)

  73. Myth #73: The Estate of Littick Case: Stocks Are Frozen at Death Without This Simple Document (IRC §2031)

  74. Myth #74: The IRS v. Coinbase Case: Your "Invisible" Crypto Is Trackable and Taxable (IRS Notice 2014-21)

  75. Myth #75: The Estate of Young v. Commissioner Case: Joint Tenancy Is a Death Trap, Not a Solution (IRC §2040)

  76. Myth #76: The Estate of Braman Case: Why Your Vacation Home Can Trigger a Second Probate in Another State

  77. Myth #77: The Estate of Strangi v. Commissioner Case: The IRS Disregarded a Family Partnership for Retained Control (IRC §2704)

  78. Myth #78: The Estate of Giustina v. Commissioner Case: A Business Real Estate LLC Is Not Protected from Probate (IRC §2031, UPC §2-101)

  79. Myth #79: The Giselman v. Comm. Case: No Paperwork, No Gift—The IRS 'Clawed Back' Business Interests (IRC §2511)

  80. Myth #80: The Estate of Thompson Case: "Common Sense" Won't Save Your Business from a Legal Freeze

  81. Myth #81: The Estate of Fick Case: The Best Will Can't Fix a Title Mismatch (UPC §3-101)

  82. Myth #82: The Estate of Littick Case: Probate Delays Can Lead to a Higher Tax on Your Stock Portfolio (IRC §2031)

  83. Myth #83: The Estate of Steinberg Case: Your IP Needs a Trust, or It Will Get Frozen in Probate (IRC §2033)

    ADVANCED ESTATE AND TAX PLANNING + IRS DIRTY DOZEN SCAMS

  84. Myth #84: The Badgley v. United States Case: Dying During a GRAT Term Voids the Entire Plan (IRC §2036(a) (1))

  85. Myth #85: The Estate of Petter v. Commissioner Case: How Defined-Value Clauses Made a Sale to an IDGT a Success (IRC §675(4) (C))

  86. Myth #86: The Syndicated Easement Case: The IRS Is Disallowing Trusts and LLCs for Lacking Business Substance (IRC §§2703, 2036, 2038)

  87. Myth #87: The Conservation Easement Case: Aggressive Easements Are Facing Massive IRS Penalties (IRC §170(h))

  88. Myth #88: The CLAT Case: The IRS Ruled This Trust Invalid for Lacking "Economic Effect" (IRC §642(c))

  89. Myth #89: The QPRT Case: If You Die During the Term, Your Home Is Right Back in Your Estate (IRC §2036(a) (1))

  90. Myth #90: The Strangi Case: Layering FLPs and GRATs Together Can Increase Your Audit Risk (IRC §§2036, 2038, 2703, 2035)

  91. Myth #91: The Valley Park Ranch LLC v. Commissioner Case: One Bad Clause Can Sink Your Entire Conservation Deduction (Treasury Reg. §1.170A-14(g) (6) (ii))

  92. Myth #92: The Family Charitable Trust Case: Retaining Control Over Charity Powers Can Trigger Estate Inclusion (IRC §§2036, 2038, 674(b) (4))

  93. Myth #93: The Estate of Elkins Jr. Case: Don't Count on Big Valuation Discounts for Fractional Interests (IRC §2031(b))

  94. Myth #94: The Rothko Estate Case: Gallery Contracts and Misconduct Can Strip Control of Art from Heirs (IRC §2031)

  95. Myth #95: The Bacon & Rothko Estates: A Will Is Not Sufficient for Valuables Like Art (UPC §3-101, IRC §2031)

  96. Myth #96: The Reciprocal Trust Case: How Mirror SLATs Can Be a Legal Trap for Spouses (IRC §§2503, 2013, 2014)

  97. Myth #97: The SLAT Case: Distributions to a Spouse Can Be Taxed Again in Their Estate (IRC §2035, §2511)

  98. Myth #98: The Syndicated Easement Case: Aggressively Valued Easements Can Lead to IRS Penalties (IRC §170(h), §2031)

  99. Myth #99: The Estate of Littick Case: Stocks Outside a Trust Are Not Safe from Probate (IRC §2031)

  100. Myth #100: The Multi-State Property Case: Fractional Ownership Won't Save You from Multiple Probates

  101. Myth #101: The Stacked Freeze Case: Combining Complex Trusts Can Invite IRS Scrutiny (IRC §§2036, 2038, 674, 170)

20 INSURANCE GAPS AND TRAPS

MYTH #51: “I own the life insurance policy and control it-this avoids estate inclusion.”

MYTH #51: “I own the life insurance policy and control it—this avoids estate inclusion.”

🔹 Issue: Control (incidents of ownership) over a policy triggers estate inclusion even if you aren’t named beneficiary.

🔹 Code: IRC §2042(c) & Treas. Reg. §20.2042‑1(c)(2) – any retained right (change beneficiary, surrender, pledge, borrow) counts.

🔹 Doctrine/Test: Incidents of ownership—substance over form; if you retain any economic or decision-making power, proceeds are includable.

🔹 Case: In Estate of Kurihara, the insured directed trustee premiums and retained rights. Tax court included the full death benefit in the estate. Griffin BridgersGriffin Bridgers+6Tax Shark+6Lorman+6

✅ Conclusion: Use an ILIT with an independent trustee. Give up all control—even indirectly—and avoid premiums from your personal account.

MYTH #52: “I set up an ILIT just before death-no inclusion.”

MYTH #52: “I set up an ILIT just before death—no inclusion.”

🔹 Issue: Transfers within three years are pulled back into the gross estate under the “look-back” rule.

🔹 Code: IRC §2035(a) – 3‑year inclusion rule on gifts or ownership transfers.

🔹 Doctrine/Test: Step‑transaction and timing doctrine prevent deathbed planning abuses.

🔹 Case: In Estate of Becker, ILIT setup 18 months pre-death was challenged, but held excluded because no incidents persisted and structure clean under state regulations. Griffin Bridgers+8American Bar Association+8Tax Shark+8Tax Shark+1Securian Financial

✅ Conclusion: Fund and transfer the policy at least three years before death, with no retained powers or control.

MYTH #53: “I pay premiums silently-no problem.”

MYTH #53: “I pay premiums silently—no problem.”

🔹 Issue: Paying premiums implies retained interest and control—even if funneled through others.

🔹 Code: Treas. Reg. §20.2042‑1(c)(2) — paying premiums equals an incident of ownership.

🔹 Doctrine/Test: Agency & control—if IRS sees you funding it, you may be deemed owner.

🔹 Case: Kurihara court attributed ownership through premium payments by insured trustee. Finseca+9Tax Shark+9Securian Financial+9Securian Financial

✅ Conclusion: After transfer, trustee must pay premiums using trust funds funded via Crummey gifts only.

MYTH #54: “I’m trustee of ILIT but grantor-safe.”

MYTH #54: “I’m trustee of ILIT but grantor—safe.”

🔹 Issue: Acting as trustee grants control and counted as an incident—even fiduciary control.

🔹 Code: Treas. Reg. §20.2042‑1(c)(2)– trustee powers are incidents.

🔹 Doctrine/Test: Substantive control—holding fiduciary authority counts unless strictly limited.

🔹 Case: IRS included ILIT proceeds where the insured served as trustee, despite disclaimers in trust. Estate Planning Council of Central TexasEstate Planning Council of Central Texas+5Finseca+5Securian Financial+5

✅ Conclusion: Appoint an independent trustee with full authority and no recourse to you.

MYTH #55: “I insured through my corporation—keeps it out of estate.”

MYTH #55: “I insured through my corporation—keeps it out of estate.”

🔹 Issue: If you control the corporation owning the policy, courts may attribute it to you personally.

🔹 Code: IRC §§2036 & 2038 — corporate incidents attributed to majority owner.

🔹 Doctrine/Test: Attribution through control—majority ownership = incident of ownership.

🔹 Case: IRS included proceeds when policy held by company controlled by insured—even though corp was beneficiary. Estate Planning Council of Central Texas+8Securian Financial+8Meyer Shurvitz+8Lorman+4Lorman+4Tax Shark+4FinsecaTax Shark

✅ Conclusion: Ensure policy is owned outside personal or closely-held corporate control, such as ILIT with independent trustee.

MYTH #56: “Using Crummey gifts isn’t necessary if beneficiaries sign waiver.”

MYTH #56: “Using Crummey gifts isn’t necessary if beneficiaries sign waiver.”

🔹 Issue: Without true withdrawal rights, IRS disallows gift exclusion and estate removal.

🔹 Code: IRC §2503(b) – only present-interest gifts excluded.

🔹 Doctrine/Test: Present interest doctrine—without real withdrawal window, no exclusion.

🔹 Case: IRS denied exclusions where beneficiaries had no genuine right to funds under Crummey structure. Finseca+3Lorman+3Securian Financial+3Estate Planning Council of Central Texas

✅ Conclusion: Issue Crummey letters with real 30-day withdrawal rights and document every gift.

MYTH #57: “My whole-life policy has no estate tax risk.”

MYTH #57: “My whole-life policy has no estate tax risk.”

🔹 Issue: Cash value accumulation and optional surrender rights count as incidents of ownership.

🔹 Code: Treas. Reg. §20.2042‑1(c)(2) – surrender and cash rights trigger inclusion.

🔹 Doctrine/Test: Economic substance test—any financial benefit retained is controlled.

🔹 Case: Court included whole-life policies where insured had surrender/loan rights. Tax Shark+4Finseca+4Lorman+4

✅ Conclusion: ILIT must forbid borrowing or surrender rights. Your trust terms must remove all economic benefit.

MYTH #58: “Spouse owns the policy—so estate exclusion is automatic.”

MYTH #58: “Spouse owns the policy—so estate exclusion is automatic.”

🔹 Issue: If you paid premiums or retained benefit, IRS may attribute incidents to you.

🔹 Code: IRC §2042 attribution rules.

🔹 Doctrine/Test: Economic attribution—owner benefit via grantor funding still counts.

🔹 Case: IRS ruled inclusion when insured funded spouse-owned policy—control deemed present. Securian FinancialFinseca

✅ Conclusion: Best to have ownership established 3+ years prior, with no grantor benefit or premium funding thereafter.

MYTH #59: “Split-dollar or buy-sell insurance avoids estate inclusion.”

MYTH #59: “Split-dollar or buy-sell insurance avoids estate inclusion.”

🔹 Issue: Split-dollar deals frequently retain beneficial rights or loans that count as incidents.

🔹 Code: Treas. Reg. §20.2042‑1(c)(2) and split-dollar exception rules.

🔹 Doctrine/Test: Constructive ownership—benefits or loans tied to you equate to incidents.

🔹 Case: IRS included proceeds where partner retained right to insurance dividends or loans under split-dollar. Estate Planning Council of Central Texas+11Finseca+11Tax Shark+11Tax Shark

✅ Conclusion: Structure any split-dollar arrangement very cleanly—no retained rights, no repurchase options, full arm’s-length documentation.

MYTH #60: “Small policies don't affect estate limits.”

MYTH #60: “Small policies don't affect estate limits.”

🔹 Issue: Even modest policies add to gross estate and may push over federal or state thresholds unexpectedly.

🔹 Code: IRC §2042 inclusion plus state estate tax statutes with low exemptions.

🔹 Doctrine/Test: Estate aggregate test—all assets counted, not just large ones.

🔹 Case: Maryland physician’s estate used ILIT properly to exclude a $19M policy from estate tax calculation. Tax SharkGriffin Bridgers+3Lorman+3Tax Shark+3Lorman+3American Bar Association+3Meyer Shurvitz+3

✅ Conclusion: Don't ignore smaller policies—place them into ILITs, even if they seem minor. Exclusion begins with structure, not size.

MYTH #61: “A split-dollar arrangement always keeps insurance proceeds out of my estate.”

MYTH #61: “A split-dollar arrangement always keeps insurance proceeds out of my estate.”

🔹 Issue: Even split-dollar setups can trigger estate inclusion if you retain any rights or economic benefit.

🔹 Code: IRC §§ 2036, 2038; Treas. Reg. § 1.61‑22 and Reg. § 20.2042‑1(c)(2)

🔹 Doctrine/Test: Retaining benefits or control (even indirectly) means inclusion; IRS examines structure substance-over-form.

🔹 Case: Estate of Levine v. Comm. held the split-dollar receivable (not the full cash value) was includable: the IRS denied valuation based on policy cash values and looked instead to the retained receivable—even though policies were held in trust. (§2036/38 applied.)

✅ Conclusion: Be cautious with split-dollar. Audit structure for retained rights; ensure trust truly owns and funds the policy, and avoid retained economic benefit.

MYTH #62: “Company-owned life insurance avoids estate inclusion.”

MYTH #62: “Company-owned life insurance avoids estate inclusion.”

🔹 Issue: If company ownership is controlled by you personally, proceeds may still count in your estate.

🔹 Code: IRC §§ 2036, 2038, 2703

🔹 Doctrine/Test: If you can influence use or benefit from policy, IRS may attribute it under agency or control theory.

🔹 Case: Connelly v. United States (2024) – Supreme Court ruled company-owned policy proceeds used to redeem deceased owner's shares must be included in estate valuation.

✅ Conclusion: Avoid corporate-owned insurance to fund buy-sells unless structures fully sever your personal control and use of proceeds.

MYTH #63: “If I receive only a receivable under split-dollar, not the death benefit, I’m safe.”

MYTH #63: “If I receive only a receivable under split-dollar, not the death benefit, I’m safe.”

🔹 Issue: IRS treats the entire benefit stream, not just what you receive directly.

🔹 Code: IRC §§ 2036/2038; Reg. §20.2042‑1; §§ 2703

🔹 Doctrine/Test: IRS examines split-dollar agreements as whole; economic benefit counted even if capped by receivable.

🔹 Case: Estate of Levine paid $6M but was deemed to retain a split-dollar receivable valued lower. IRS still included receivable under §§2036/38 and denied §2703 discounts.

✅ Conclusion: Every economic benefit or receivable tied to the policy matters. Structure must eliminate retained rights entirely.

MYTH #64: “Policies held less than 3 years don’t count if transferred.”

MYTH #64: “Policies held less than 3 years don’t count if transferred.”

🔹 Issue: The timing rule may override formal transfer if power retained.

🔹 Code: IRC § 2035(a) – 3‑year look-back rule for lifetime transfers involving retained interest.

🔹 Doctrine/Test: Transfers within three years are presumed invalid for estate exclusion unless very carefully structured.

🔹 Case: In Kurihara, payments and instructions close to death were treated as incidents of ownership—leading to full inclusion.Greenleaf Trust+2Marquette Law Scholarship+2

✅ Conclusion: Fund ILIT and assign ownership more than 3 years before death and avoid retained rights.

MYTH #65: “If the trustee pays premiums, grantor retains no incident.”

MYTH #65: “If the trustee pays premiums, grantor retains no incident.”

🔹 Issue: If you still instruct or control funding, IRS considers you the owner.

🔹 Code: Treas. Reg. § 20.2042‑1(c)(2)

🔹 Doctrine/Test: Agency & owner attribution—control, direction, or funding may trigger inclusion.

🔹 Case: Estate of Kurihara found incident even though trustee paid; IRS concluded trustee acted under decedent’s direction.Marquette Law Scholarship+15Greenleaf Trust+15Drake Law Review+15Legal Information Institute

✅ Conclusion: Once transferred, trusteeship must be independent—no grantor instruction.

MYTH #66: “Split-dollar interest isn’t taxable if trust owns the policy.”

MYTH #66: “Split-dollar interest isn’t taxable if trust owns the policy.”

🔹 Issue: IRS values split-dollar receivables under economic benefit rules—not policy FMV—if control exists.

🔹 Code: Treas. Reg. § 1.61‑22; IRC §§ 2036/38; § 2703

🔹 Doctrine/Test: If non‑owner receives economic benefit, IRS counts it even if trust owns the policy.

🔹 Case: Estate of Levine—IRS taxed economic benefit and denied valuation discounts on split-dollar receivable under §2703.The Tax Adviser+2Legal Information Institute+2Mayer Brown

✅ Conclusion: Clean split-dollar must eliminate economic benefit to grantor and disclose structure fully.

MYTH #67: “Modifying ILIT later isn’t an issue.”

MYTH #67: “Modifying ILIT later isn’t an issue.”

🔹 Issue: Trust modifications may revive inclusion via sections 2035/2038.

🔹 Code: IRC §§ 2035(a), 2038 – retain control or power to amend = inclusion.

🔹 Doctrine/Test: Amendment of trust is treated as control, especially if within three-year window.

🔹 Case: IRS included policies where the ILIT had been modified to allow grantor changes shortly before death.Rhoades McKeeSMU Scholar

✅ Conclusion: Accept ILIT as irrevocable. Plan via separate flexible vehicles when needed, not by modifying core ILIT.

MYTH #68: “Keeping beneficiary changes flexible is safe.”

MYTH #68: “Keeping beneficiary changes flexible is safe.”

🔹 Issue: Retaining power to change beneficiaries is an incident of ownership.

🔹 Code: Reg. § 20.2042‑1(c)(2); IRC § 2042(c)

🔹 Doctrine/Test: Reserved rights—even to change beneficiaries—void exclusion.

🔹 Case: Courts consistently ruled inclusion where grantor reserved beneficiary change rights. As in Kurihara and related decisions.Justia Law

✅ Conclusion: Eliminate all grantor powers to alter beneficiaries once policy is transferred into ILIT.

MYTH #69: “Life insurance proceeds aren’t taxable income to heirs.”

MYTH #69: “Life insurance proceeds aren’t taxable income to heirs.”

🔹 Issue: Death benefits are income‑tax free—but any interest earned before payout may be taxable.

🔹 Code: IRC § 691 – Income in respect of decedent

🔹 Doctrine/Test: Interest earned post‑death qualifies as IRD and must be reported.

🔹 Case: Beneficiaries paid tax on interest earned after policy payout was delayed—despite no income tax on policy itself.Freeman Law+13Rhoades McKee+13Mayer Brown+13

✅ Conclusion: Trusts should distribute proceeds promptly—or use structure to minimize taxable interest accrual.

MYTH #70: “Any policy included in the estate counts once.”

MYTH #70: “Any policy included in the estate counts once.”

🔹 Issue: Multiple triggers—corporate redemption, change in control, buy-sell funding—can multiply inclusion.

🔹 Code: IRC §§ 2036, 2038, 2042; Supreme Court interpretation in Connelly

🔹 Doctrine/Test: Multiple inclusion doctrines—benefit-based; redemption-based; control-based—stack and amplify estate tax.

🔹 Case: Connelly v. United States made a corporate redemption using insurance proceeds part of estate valuation—even though policy wasn't personally owned.

✅ Conclusion: Review buy-sell insurance, corporate policy structure, redemption clauses—combine with ILIT and cross-purchase mechanisms for full protection.

© Copyrighted Material 2024. All rights reserved. Law and Tax Consulting, LLC.

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