In the 1985 case Posadas de Puerto Rico Associates, DBA Condado Holiday Inn v. Tourism Company of Puerto Rico et al., the U.S Supreme Court upheld a law in Puerto Rico that restricted advertising for casinos to residents outside of the commonwealth. The court ruled 5-4 that this restriction did not violate First Amendment rights to free speech because it served a substantial government interest and was no more extensive than necessary. The majority opinion argued that if the government could ban an activity (in this case gambling), it could also regulate advertisements promoting said activity. This decision expanded on previous rulings regarding commercial speech and has been cited in subsequent cases involving restrictions on advertising for products or activities deemed harmful or controversial.

In the dissenting opinion for Posadas de Puerto Rico Associates v. Tourism Company of Puerto Rico, Justice Brennan argued that the majority's decision was a significant departure from established First Amendment jurisprudence. He contended that commercial speech should not be treated differently than other types of protected speech and criticized the majority for applying a lower standard of review to restrictions on commercial speech about lawful activities. Furthermore, he disagreed with the majority's assertion that because government can ban an activity entirely it can also restrict advertising for that activity, arguing this logic could justify censorship in many areas where it is currently impermissible. Finally, he expressed concern over potential misuse of paternalistic justifications to suppress information about legal but potentially harmful products or activities.