Beckett G. Cantley, Repeat as Necessary: Historical IRS Policy Weapons to Combat Conduit Captive Insurance Company Deductible Purchases of Life Insurance, 13 U.C. Davis Bus. L.J. 1 (2012).
Summary. This article argues that the IRS is likely to view an arrangement where a small business owner funds a CIC for the primary purpose of obtaining deductions on owner-insider life insurance premium payments as similarly abusive to prior listed transactions involving IRC § 419 plans, IRC § 412(e)(3) plans, and IRC § 831(b) PORCs, as well as in violation of its historical tax enforcement policies against discriminatory insider tax benefits, and improper uses of key man life insurance. The article states that the IRS should view the use of an entity as a direct conduit for achieving an impermissible tax-deductible premium payment in the same manner as it would the taxpayer taking the deduction directly. This article discusses (1) the history of IRS enforcement and tax policy in combating improper tax uses of life insurance, and (2) evaluates the likely success of applying these historical arguments to establish that insider life insurance premiums are not deductible, nor should any tax-deducted funds be used to purchase such policies.