Redleaf v. Commissioner – Cash payments are property settlement, not deductible alimony

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Abstract: Pursuant to a marital termination agreement from 2008, the husband in Redleaf v. Commissioner deducted $51 million in deferred cash payments to his ex-wife. The U.S. Court of Appeals for the Eighth Circuit Court affirmed that the payments weren’t deductible as alimony under the tax law that was in effect at the time the agreement was executed. This article summarizes the case and highlights the importance of considering tax issues when executing a divorce or settlement agreement. Redleaf v. Commissioner, 43 F.4th 825 (8th Cir. 2022).