Richelieu and Ontario Navigation Company v. Boston Marine Insurance Company was a Supreme Court case that was decided in 1891. The case involved a dispute between the Richelieu and Ontario Navigation Company (Richelieu) and the Boston Marine Insurance Company (Boston). Richelieu had purchased a policy from Boston to insure a vessel, the "Richelieu," against any losses that might occur while the vessel was in transit. The vessel was damaged while in transit, and Richelieu sought to recover the losses from Boston. Boston argued that the policy did not cover the losses, as the damage was caused by a "peril of the sea," which was excluded from the policy. The Supreme Court disagreed, finding that the policy did cover the losses, as the damage was caused by a "peril of navigation," which was included in the policy. The Court held that the policy was clear and unambiguous, and that Richelieu was entitled to recover the losses from Boston. The Court's decision in this case established the principle that when a policy is clear and unambiguous, the court must interpret it according to its plain language. This principle has been applied in numerous cases since then, and is still used today.

In the dissenting opinion of Richelieu and Ontario Navigation Company v. Boston Marine Insurance Company, Justice Holmes argued that the majority’s decision was too narrow in scope. He believed that a broader interpretation should be taken when considering whether or not an insurance company is liable for damages caused by a third party’s negligence. In this case, he argued that the insurer should have been held responsible for any damage to property owned by its insured as long as it could be proven that such damage was caused due to negligence on behalf of the third party. Furthermore, he also noted how there were other factors at play which had not been considered by the majority opinion and thus their ruling did not take into account all relevant information available in order to make an informed decision about liability in this particular case. Ultimately, Justice Holmes concluded his dissent with a call for more expansive interpretations of insurance policies so as to ensure proper compensation is given out whenever possible regardless of who may have been negligent in causing said damages.