In Adderley et al. v. Florida, the U.S Supreme Court upheld a trespassing conviction of several civil rights demonstrators who had protested on jailhouse grounds without permission. The case was brought by Harriet Louise Adderley and 31 other students from Florida A&M University who were arrested for "trespass with a malicious and mischievous intent" after demonstrating against racial segregation at the Leon County Jail in Tallahassee, Florida. They argued that their First Amendment rights to freedom of speech and assembly were violated by this arrest. The court ruled 5-4 in favor of the state of Florida, stating that public property is not automatically available for any purpose simply because it is owned by the public; rather its use can be restricted based on its designated purpose or nature (in this case being a jail). Therefore, according to majority opinion written by Justice Black, there was no constitutional issue with punishing those whose presence obstructed normal operation of facilities like jails.

In the dissenting opinion for Adderley v. Florida, Justice Douglas argued that the majority's decision was a departure from established First Amendment principles protecting peaceful protest and assembly. He contended that the trespass law used to arrest and convict the protesters was applied in a discriminatory manner, targeting civil rights demonstrators while ignoring other groups who had assembled at the jail without permission. Douglas also criticized his colleagues for failing to recognize jails as public spaces where citizens have a right to express their grievances with government actions. Furthermore, he expressed concern about potential chilling effects on free speech and assembly resulting from this ruling, warning it could be used by authorities across America to suppress protests under vague trespass laws.