The Tax Court Deals a Blow to “Micro-Captive” Insurance Company

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Jason B. Freeman

Jason B. Freeman

Managing Member


Mr. Freeman is the founding member of Freeman Law, PLLC. He is a dual-credentialed attorney-CPA, author, law professor, and trial attorney.

Mr. Freeman has been named by Chambers & Partners as among the leading tax and litigation attorneys in the United States and to U.S. News and World Report’s Best Lawyers in America list. He is a former recipient of the American Bar Association’s “On the Rise – Top 40 Young Lawyers” in America award. Mr. Freeman was named the “Leading Tax Controversy Litigation Attorney of the Year” for the State of Texas for 2019 and 2020 by AI.

Mr. Freeman has been recognized multiple times by D Magazine, a D Magazine Partner service, as one of the Best Lawyers in Dallas, and as a Super Lawyer by Super Lawyers, a Thomson Reuters service. He has previously been recognized by Super Lawyers as a Top 100 Up-And-Coming Attorney in Texas.

Mr. Freeman currently serves as the chairman of the Texas Society of CPAs (TXCPA). He is a former chairman of the Dallas Society of CPAs (TXCPA-Dallas). Mr. Freeman also served multiple terms as the President of the North Texas chapter of the American Academy of Attorney-CPAs. He has been previously recognized as the Young CPA of the Year in the State of Texas (an award given to only one CPA in the state of Texas under 40).

The Tax Court recently issued a much-anticipated decision in Avrahami v. Commissioner. At issue: an IRS challenge to deductions taken by the taxpayer for premiums paid to a “micro-captive” insurance company.  In a victory for the IRS, the Tax Court denied the deductions at issue, finding that the amounts paid did not qualify as insurance premiums for federal income tax purposes.  In the process, the court also determined that the captive’s elections under section 831(b) (to be treated as a small insurance company) and section 953(d) (to be taxed as a domestic corporation) were invalid.

But not every issue went the way of the IRS.  While holding against the taxpayers on the substantive tax issues, the court nonetheless refused to impose penalties for the disallowed deductions.  The line drawn by the court could, perhaps, signal a potential basis for micro-captive settlements in the future.

So, for those wondering, how does this “micro-captive” thing work?  Well, it’s complicated, but here’s a nutshell summary:  Generally, a taxpayer can deduct premiums paid for insurance as “ordinary and necessary” expenses.  The insurance companies that receive those premiums are generally taxed on the premiums.  “Small” insurance companies that are eligible to make an election under section 831(b) of the Internal Revenue Code, however, are given preferential treatment: they are only taxed on their investment income, not the premiums that they receive.

Captive insurance companies, as the name implies, generally insure risks for related companies (e.g., a corporate parent may own a captive insurance company that insures certain risks).  In other words, the related party pays premiums to the captive insurance company.  Those premiums are deducted by the related party for tax purposes.

So what is a “micro-captive?”  Captive insurance companies that make a valid section 831(b) election are referred to as “micro-captives.”  Under section 831(b), the micro-captive does not have to include the premiums that it receives in income.  That’s right, the related party gets a deduction for premiums, and the micro-captive does not have to recognize the amount paid as taxable income.  All of this works, however, only if the premiums are paid for “insurance”—a term that is not explicitly defined in the Code or the Regulations. And therein lies much of the rub.

Despite its central role, the term “insurance” is not defined by the Code or the Regulations. Instead, the development of the concept has been left to the courts.  Over time, courts have primarily looked to four criteria to determine whether an arrangement constitutes “insurance” for Federal income tax purposes: (1) does the arrangement involve insurable risks?; (2) does the arrangement shift the risk of loss to the insurer?; (3) does the insurer distribute the risks among its policyholders?; and (4) is the arrangement “insurance” in the commonly accepted sense?

The 105-page, highly fact-specific opinion in Avrahami only explored two of these criteria: risk distribution and commonly accepted notions of insurance.  Thus, future decisions in this context, will put more flesh on the contours of these requirements.  But for those still reading along and figuratively sitting on the edge of your seat …  we are in luck: There are several captive cases still in the pipeline—e.g., James L. Wilson & Vivien Wilson v. Commissioner—so we may not have to wait too long.   These cases are being followed closely by the captive industry.

In the meantime, the Avrahami decision is likely to embolden the IRS in its attack on micro-captives that it views as abusive.  The IRS certainly considers it a critical win.  That means practitioners and clients should consider actively reviewing and evaluating captive arrangements in light of the recent decision, and, where appropriate, take proactive steps to strengthen their position against potential future challenges on the heels of Avrahami.  After all, risk mitigation is the name of the game here.


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