Recently, Margaret Gilbert has argued that it appears that the wisdom of a society impinges, greatly, on its freedom. In this article, I show that Gilbert’s “negative argument” fails to be convincing. On the other hand, there are important lessons, particularly for democratic theory, that can be by looking carefully, and critically, at her argument. This article will proceed as follows. First, I present Gilbert’s argument. Next, I criticize her understanding of freedom, and then, using arguments from Christopher McMahon, criticize her understanding of a wise society. Finally, I discuss how what has been said can inform how one should think about democratic theory.