The Strange and Curious Tax Treatment of Investment Expenses

To secure income, taxpayers often incur a wide range of expenses. At least theoretically, one might think that the Internal Revenue Code (“Code”) would accord all such expenses similar tax treatment, but (i) trade or business expenses and (ii) investment expenses endure the exact opposite tax treatment: the former are generally allowed, whereas the latter are commonly disallowed. The obvious question is why there is a difference in treatment between the two. This Article explores possible answers to that important question. It first traces the evolution of the Code’s dichotomous tax treatment of trade or business versus investment expenses. It then investigates possible justifications and their associated merits for the different handling of these two expense categories. With this background information in mind, to make the tax system more administrable, equitable, and efficient, this Article advocates for the deductibility of investment expenses and describes several beneficial implications associated with the institution of this proposed reform