By analyzing philanthropists as policy network actors, the paper investigates contradictory analytical indications for how their lack of accountability mechanisms may affect their ability to influence policymaking. Philanthropists’ lack of accountability mechanisms may enable them to strategically purchase legitimacy, which may increase their policy influence. Paradoxically, philanthropists’ lack of accountability mechanisms may also decrease their democratic legitimacy, which may decrease their policy influence. A model is conceptualized for testing this policy paradox of philanthropy.