Whether in the form of lotto tickets or casino table games, gambling is legally permitted in some way in virtually every U.S. state. Yet, in all but a handful of jurisdictions, federal law prohibits wagering on sporting events or professional athletes in any form. Several economically challenged states, particularly New Jersey, have been trying to authorize sports gambling within their borders as a way to raise tax revenues and support their local gambling industries. While these attempts have thus far been unsuccessful, Daily Fantasy Sports have simultaneously experienced a meteoric rise, becoming a multi-billion dollar industry. This Note examines the legal framework governing sports gambling and the grey area in which Dailey Fantasy Sports providers have been allowed to operate. It then analyzes Daily Fantasy Sports legally and qualitatively, concluding that they constitute a form of illegal sports gambling that has largely escaped regulation. Particular emphasis is placed on the hypocritical role that the major North American professional sports leagues have played in Daily Fantasy Sports’ explosive growth, while they simultaneously oppose sports gambling and fight in court to block any attempts for its legalization. Finally, this Note presents professional sports league involvement in Daily Fantasy Sports as an opportunity for states and the larger American gambling industry to gain the political capital necessary to repeal the federal sports gambling prohibition, and explores the rising tide of public and political support toward legalized sports betting on a state piecemeal basis.