A new breed of power broker debuted with the diffusion of global authority, the growth of privatization, and new information technologies in the late twentieth and early twenty-first centuries. The success of these “shadow elites” stems from their ability to break new ground with regard to conflict of interest. They conflate official and private interests without violating the law. They test both governments’ rules of accountability and businesses’ codes of competition. Moving nimbly between official and private spheres, and sometimes erasing the distinction, these players can wield more power and influence than lobbyists, interest groups, “kitchen cabinets,” and other influencers in democratic society. Largely beyond public input, they challenge the principles that have defined modern states, free markets, and democracy itself. Conventional categories are ill-suited to describe these operators and conventional means of holding them to account are also ill-equipped to do so.