In the case of Caren Cronk Thomas and Windy City Hemp Development Board v. Chicago Park District, 2001, the U.S. Supreme Court ruled in favor of the Chicago Park District's policy requiring a permit for public assemblies over fifty people on park grounds. The plaintiffs argued that this policy violated their First Amendment rights to free speech as it allowed officials too much discretion in deciding who could hold events based on content or viewpoint discrimination. However, the court disagreed with this argument stating that there were clear guidelines limiting official discretion and ensuring prompt decisions regarding permits without any bias towards content or viewpoint. Furthermore, they noted that such policies are necessary to coordinate multiple uses of limited space, prevent dangerous situations from overcrowding and minimize damage to parks' resources.

In the dissenting opinion for Caren Cronk Thomas and Windy City Hemp Development Board v. Chicago Park District, Justice Stevens argued that the majority's decision to uphold a park permit system that allowed officials to delay decisions indefinitely was unconstitutional. He contended that such a system could be used as an instrument of censorship, violating First Amendment rights by allowing government officials to suppress speech they found disagreeable or inconvenient. Furthermore, he disagreed with the majority’s view on what constituted a reasonable time limit for making decisions on permit applications. In his view, any law granting public officials power over free expression should have explicit limits in order not to infringe upon citizens' constitutional rights.