In the case of City of Springfield, Massachusetts v. Kibbe in 1986, the Supreme Court was asked to consider whether a city could be held liable under federal law for failing to provide adequate training to its police officers. The case arose after an unarmed man named Thurston was shot and killed by a Springfield police officer following a high-speed chase. The administratrix of Thurston's estate sued the city on behalf of his heirs, arguing that inadequate training had led directly to Thurston's death. However, the Supreme Court dismissed this argument due to insufficient evidence showing that lack of proper training caused such incidents routinely or predictably enough for it being considered as "city policy". Therefore, they concluded that there wasn't any direct causal link between deficient training and violation of rights protected by constitution which is necessary for establishing municipal liability under federal law.

In the dissenting opinion for City of Springfield, Massachusetts v. Kibbe, Justice O'Connor argued that the majority's decision to dismiss certiorari as improvidently granted was incorrect and premature. She contended that there were two significant issues at stake: whether a municipality can be held liable under 42 U.S.C §1983 for failure to train its police officers adequately in high-speed chase procedures, and if so, what standard should govern such liability. According to her view, these questions deserved full consideration by the court due to their importance in clarifying municipal liability law and ensuring public safety during police chases. The dismissal left lower courts without clear guidance on how they should handle similar cases in future. Therefore she disagreed with the majority’s decision not only because it avoided addressing critical legal questions but also because it undermined uniformity among federal courts' decisions.