Commissioner Archives

Tax Court Rejects Offer in Compromise Despite Extraordinary Personal Circumstances

Aug 14, 2026

In Tooke v. Commissioner,[1] the United States Tax Court recently reaffirmed the considerable discretion afforded to the Internal Revenue Service Independent Office of Appeals (“Appeals”) when evaluating collection alternatives. Although the taxpayer presented compelling evidence of significant personal hardship, including a Parkinson’s disease diagnosis, the financial consequences of a contentious divorce, and substantial expenses associated…
Read More

Early Trust Terminations: Income Tax Considerations

Asset Protection, Estate Administration, Estate Planning

Feb 6, 2026

Use of irrevocable trusts is common in a number of planning scenarios – tax planning, estate planning, business succession, Medicaid qualification, asset protection, etc. Just like there are several reasons irrevocable trusts are created, there can be reasons why a trust may be terminated before the expiration of the term stated in the trust agreement.[1]…
Read More

Recent Microcaptive Case Undermines Promoted Structure

Asset Protection, Business Transactions, Cases, Income Tax, Tax, Tax Controversy, Tax Court

Apr 9, 2025

A recent Tax Court decision underscores an increasingly rigorous examination of Section 831(b) microcaptive insurance arrangements.[1] This ruling may be insightful to taxpayers considering or currently operating microcaptives, has broad implications for businesses seeking legitimate tax incentives created by Congress. Overview of the Case The case at hand involves the Internal Revenue Service’s (“IRS”) rejection…
Read More

Checks Written Before But Cashed After Death Includible in Gross Estate

Cases, Estate and Gift Tax, Tax, Tax Court

Jul 28, 2022

In a recent Tax Court case[1], the Court held that the combined value of ten checks written prior to the decedent’s death, but cashed after his death, was included in the gross estate of the decedent. However, as discussed below, the IRS had conceded that three of the ten checks were not included in the…
Read More

Make A Payment

Tag: Commissioner

Tax Court Rejects Offer in Compromise Despite Extraordinary Personal Circumstances

Early Trust Terminations: Income Tax Considerations

Recent Microcaptive Case Undermines Promoted Structure

Checks Written Before But Cashed After Death Includible in Gross Estate

Directions

Income Tax Planning with Non-Grantor Trusts After OBBBA

Tax Court Rejects Offer in Compromise Despite Extraordinary Personal Circumstances

IRS Provides Guidance on Dividing Inherited IRAs Through Trustee-to-Trustee Transfers