In the case of State of Maryland v. State of West Virginia in 1909, the U.S Supreme Court was tasked with resolving a boundary dispute between these two states. The disagreement centered around the interpretation and location of the Fairfax Stone, which had been used as a marker for land granted to Lord Fairfax by Britain before American independence. Both states claimed that their historical boundaries extended beyond this point into each other's current territory. After considering evidence from maps, surveys and historical documents presented by both sides, the court ruled in favor of West Virginia's claim on most disputed areas except one small portion known as "the gore," which was awarded to Maryland due to an error made during an earlier surveying process conducted in 1852.

In the dissenting opinion for the case of State of Maryland v. State of West Virginia, Justice Holmes disagreed with the majority's interpretation and application of historical documents to determine state boundaries. He argued that there was insufficient evidence to definitively establish where Charles II intended the boundary line between Pennsylvania and Maryland to be when he granted land charters in 1681. Furthermore, he contended that even if such intent could be determined, it should not necessarily dictate present-day borders due to changes over time in geographical knowledge and territorial claims. Instead, Holmes suggested a more pragmatic approach based on current realities rather than historical speculation would better serve justice and maintain peace among states.