In this Article, prepared as part of a Symposium on the intersection of corporations and money in politics, I illustrate the various ways that corporations can spend their money to influence politics in America and the relevant disclosure rules (or lack thereof)that track this political activity. I also highlight opportunities for individuals to exploit corporate transparency loopholes to illegally spend money in American politics and address the question whether proof of possible nefarious activity is sufficient to justify regulations targeting actual nefarious activity, drawing on recent debates about voter fraud. Finally, I argue that campaign finance laws have been created, justified, implemented, and interpreted in relative isolation from one another, creating unnecessary (though perhaps anticipated) loopholes in enforcement that undermine the goals of oversight and accountability in campaigns and elections. Campaign finance regulations can only be effective insofar as they respond to the dynamic character of political campaigns. Thus, policymakers should refine their “comprehensive” reforms to better address the integrated nature of campaign finance. Given the strategic nature of political actors, this shift will likely result in more emphasis on as‐applied challenges in the courts.