Conventions and leaders are believed to be the two pillars of justice and order in society. This paper evaluates this proposition and draws attention to two intriguing ways in which these pillars can malfunction. The argument is constructed by creating two new games, Greta’s Dilemma and the Incarceration Game. An awareness of these problems can help us use our ‘moral intention’ to reexamine our own collective behavior and to design prior conventions, which limit the power of the leader.