There is a long history of cases interpreting whether a theft loss deduction for securities fraud is allowable for personal income taxes. The cases require that for a theft loss to be actionable as such, it would have to meet the requirements of the common law definition of theft in the U.S. state in which it occurred. This generally requires direct privity between the person claiming the loss and the person who committed the theft. Because most securities transactions are brokered, the direct privity is lost and a theft loss deduction is denied in favor a capital loss. Recently, in a case of first impression, the Tax Court was presented with a similar issue involving the worth of assets for estate taxes. Instead of using the reasoning presented in income tax cases, the Tax Court allowed a theft loss deduction on estate taxes where a Ponzi scheme was uncovered while the estate owned a limited liability company. The sole assets of the company were shares of the security that was involved in the Ponzi scheme. This Article examines the history of the privity requirement for deducting a theft loss for income taxes and how that reasoning now differs from the tax treatment for estate taxes. The Article concludes that there should not be a difference in treatment and that direct privity should not be required for either income or estate taxes.