This article discusses the tension that exists between the recent textualist approach taken in the U.S. Supreme Court and the judicially developed substance-over-form doctrines that pervade tax law. It sets forth Justice Antonin Scalia’s textualist approach, provides an overview of the substance-over-form doctrines, and then analyzes whether the current Supreme Court would uphold a case that overrode the literal text of the Internal Revenue Code on the basis of one of the doctrines. The article concludes that the current Supreme Court would reject any of these doctrines if faced with the issue.