This Note argues that the hallmark of illegal punishment under the Bill of Attainder Clause is the targeted deprivation of life, liberty, or property. While many have highlighted the due process function of prohibiting legislative punishment, no commentator has paid adequate attention to the substantive rights that this prohibition was designed to protect. The result has been widespread confusion as to when Congress may legislate with particularity and when it may not. This confusion manifested itself recently when a federal district court in New York struck down a law barring federal funding for the scandal-plagued Association of Community Organizations for Reform Now (ACORN). The Second Circuit reversed that decision on appeal, but it did nothing to fill the vacuum of guidance for determining when an individualized enactment is a legitimate regulation and when an illegal punishment. Beginning with the Constitution’s special emphasis on the rights of “life, liberty, [and] property,” this Note’s interpretation finds ample support in the text, structure, and history of the Constitution. It also reveals an underlying symmetry in the protections of the Due Process and Bill of Attainder Clauses, which together prevent arbitrary deprivations at the hands of the executive and legislative branches. And finally, the Note’s central argument fits with the common intuition that legislators, like executive officials, have much greater latitude when dealing with subsidies rather than individual rights.