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Part I of this article traces the evolution in the tax treatment of litigation damages from 1918 through the enactment of the 1996 Amendments and reviews the various rationales that have been offered for such treatment. In Part II, I set forth a number of hypothetical cases illustrating some of the issues created by the 1996 Amendments. In Parts III through Part VI, I set forth my analyses of these issues. Finally, In Part VII, I critique the 1996 Amendments and make a proposal that would eliminate much of the uncertainty and inequity that the 1996 Amendments created while satisfying an apparent concern that led to their enactment.