Recent dialogue struggling to apply traditional methods of wartime legalism to the battle against terrorism has neglected one of Congress's oldest constitutional powers: the power to issue letters of marque and reprisal. Historically, letters of marque permitted private individuals, referred to as privateers, to pursue legitimate war aims for private gain. Not infrequently, nations dispatched privateers in an effort to thwart piracy. Piracy and terrorism share many parallels, suggesting that customization of tools effective against piracy could provide a vital resource in the fight against terrorism. This Note: (1) posits that despite international and domestic legal and policy obstacles, the return of privateers under letters of marque to combat terrorism is viable as a supplement to the wartime status quo; (2) offers solutions to various constraints; and (3) ultimately supplies a prologue to future debate.