In the case of Jacobs et al. v. New York, 1966, the U.S Supreme Court was asked to consider whether a state law that prohibited loitering without lawful purpose violated constitutional rights to freedom of speech and assembly. The appellants were convicted under this law for standing on a street corner in New York City and refusing to move when ordered by police officers. They argued that their convictions infringed upon their First Amendment rights as well as their Fourteenth Amendment right to due process. The Supreme Court affirmed the constitutionality of the anti-loitering statute, ruling it did not infringe upon any protected liberties or violate due process requirements. The court held that states have an interest in maintaining order on public streets and preventing potential disturbances; therefore they can regulate behavior such as loitering if there is no clear lawful purpose behind it.

In the dissenting opinion for Jacobs et al. v. New York, Justice Harlan argued that the majority's decision to overturn a conviction based on evidence obtained through an unauthorized wiretap was misguided and overly broad in its interpretation of privacy rights under the Fourth Amendment. He contended that not all conversations should be protected from government intrusion, particularly when they involve criminal activity. Furthermore, he criticized the majority for failing to consider whether or not there were any less intrusive means available to law enforcement officials before resorting to wiretapping. In his view, this failure undermined their argument about unreasonable searches and seizures because it did not take into account practical considerations related to crime detection and prevention efforts by police forces.