In the 1969 case Richard S. v. City of New York, a minor named Richard S., through his guardian, sued the city for injuries he sustained from falling into an open manhole. The plaintiff argued that the city was negligent in maintaining its sewer system and should be held liable for his injuries. However, under New York law at that time, municipalities were immune from liability arising out of their governmental functions unless they had previously assumed such liability by statute or charter provision. The U.S Supreme Court ruled in favor of the City of New York stating that it could not be held responsible because it was performing a governmental function when maintaining its sewers and did not have any statutory obligation to maintain them safely. This ruling upheld municipal immunity doctrine which protects cities from being sued for damages resulting from negligence while carrying out government functions unless there is explicit legislation allowing such lawsuits.

The dissenting opinion in the case of Richard S. v. City of New York argued that the majority's decision to uphold a law prohibiting loitering was an infringement on individual liberties protected by the Constitution. The dissenters believed that this law was too broad and vague, potentially leading to arbitrary enforcement and punishment for innocent behavior. They also expressed concern about potential abuse of power by police officers who could use such laws as a pretext for stopping and questioning individuals without reasonable suspicion or probable cause, thus violating their Fourth Amendment rights against unreasonable searches and seizures. Furthermore, they contended that criminalizing loitering might disproportionately affect certain groups like homeless people or racial minorities who are more likely to be targeted under such laws due to societal biases or prejudices.