Political spending, in all of its various permutations, lies at the nexus between campaign finance law and pay-to-play law. Both of these legal doctrines seek to minimize the corrupting effects of money upon elected officials and candidates, and both impose various caps and restrictions on political contributions in order to do so. Over the past half-century, however, the Supreme Court has struggled to define what sort of activity constitutes corruption in the political sphere. In light of its decisions in 2010s Citizens United v. FEC and 2014s McCutcheonv. FECtwo seminal cases that dramatically altered campaign finance regulation the Court now appears to recognize that the act of gaining access to elected officials via political spending does not constitute quid pro quo corruption or the appearance thereof. This view has led to deregulation of the legal framework of campaign finance in recent years. Furthermore, at present, presupposing corruption on the part of elected officials or candidates is not always a lawful assumption upon which laws or regulations governing political spending can be based. It thus follows that the corruption-based rationale at the heart of certain federal, state, and local pay-to-play laws may also be subject to challenge. This Note examines the Courts shifting views on corruption, applies it to various pay-to-play laws currently in effect, and ultimately concludes that the legal and constitutional framework for much of pay-to-play law, as it currently stands, rests on shaky ground.