Dissatisfaction with the complexity of the income tax is nothing new. Still, recent decades have seen anything but a decrease in the tax law’s complexity. The seemingly inexorable rise in complexity has attracted the attention of scholars, inspired politicians and, of course, frustrated taxpayers. Typically it is assumed that what puts simplicity, or at least simplification, out of reach is a lack of political viability. In other words, the lack of a political constituency for tax simplification makes it inevitable that other tax policy concerns will take precedence over simplicity. As a result, simplification becomes the tax law’s equivalent of a perennially ill-fated New Year’s resolution.