No topic splits the captive insurance world more than the issue of life insurance — or, more specifically, whether or not a captive can purchase a whole life policy as part of its investment portfolio.
Those in favor point to the stable returns offered by whole life and the fact that banks are allowed to purchase BOLI as primary reasons for the policy.
Those against the practice cite anti-avoidance law along with the IRS's long history of successfully attacking more aggressive life insurance plans as negative factors. Adding further fuel to the fire is the lack of any formal guidance from the IRS on the issue, leaving both camps with enough legal wiggle room to claim validation.
I have always fallen in the negative camp, largely based on anti-avoidance law concerns. By way of quick background, anti-avoidance law is a series of judicial doctrines used by the courts and the IRS to attack transactions largely on "substance over form" grounds. This doctrine has a long and extremely convoluted legal history, which can be traced to the Gregory v. Helvering case, and stretches to well over 1,000 citations in cases, law review articles and legal treatise. Highly questionable annuity and life insurance transactions are at the center of several of the more famous citations, such as Knetsch (which involves an annuity transaction) and In Re CM Holdings (which is one of four COLI cases from the 1900s and early 2000s).
Firmly hardening my antagonism to this transaction is a recent law review article by Beckett Cantley, law professor at John Hopkins School of Law in Atlanta. His piece, "Historical IRS Policy Weapons to Combat CIC Deductible Purchases of Life Insurance," provides the most in-depth treatment of this transaction, highlighting the IRS' successful attacks on more aggressive life insurance planning, the policy reasons behind those attacks and the application of the reasoning of those successful prosecutions to captive purchases of life insurance.
He concludes, "The IRS will likely view an arrangement where a small business owner funds a CIC for the primary purpose of obtaining deductions on life insurance premium payments ("Insurance Transaction") as similarly abusive to prior listed transactions involving I.R.C. § 419 plans, I.R.C. § 412(e)(3) plans, and I.R.C. § 831(b) PORCs."
Professor Cantley outlines the basic argument that would allow the IRS to successfully challenge these transactions.
The starting point is section 264(a) of the tax code, which states: "No deduction shall be allowed for — (1) Premiums on any life insurance policy, or endowment or annuity contract, if the taxpayer is directly or indirectly a beneficiary under the policy or contract."
