This essay, written for a symposium on insider trading in the Washington University Journal of Law and Policy, explores the different paths taken by the United States and the European Union with respect to who is subject to the prohibition on insider trading. After providing an overview of the difference between the U.S. and the E.U. prohibition, the essay explores the different outcomes that would occur under U.S. versus E.U. law in several high profile insider trading cases of recent years. The essay also addresses the jurisdictional reach of each regime’s prohibition and considers the normative lessons of this real world experiment in taking different paths.