In the case of State of Maryland v. State of West Virginia in 1909, the Supreme Court was tasked with settling a boundary dispute between these two states. The disagreement arose from differing interpretations of colonial-era charters and subsequent surveys that defined their shared border along the south branch of the Potomac River. Maryland claimed its territory extended to Fairfax Stone, while West Virginia argued it only reached to North Branch based on Lord Fairfax's survey in 1746. After examining historical documents and evidence presented by both parties, including royal charters dating back as far as 1632 for Maryland and 1664 for New Jersey (which originally included what is now West Virginia), the court ruled in favor of West Virginia's claim that its border extends up to Fairfax Stone at headwaters instead North Branch where river splits into multiple branches further downstream. This decision effectively confirmed existing de facto boundaries established over time through settlement patterns rather than strictly adhering to original charter language or early survey lines which were often inaccurate due to primitive mapping techniques available during colonial times.

In the dissenting opinion for the case of State of Maryland v. State of West Virginia, Justice Holmes disagreed with the majority's decision to favor West Virginia in a boundary dispute. He argued that historical documents and maps from colonial times clearly showed that Maryland's original charter granted it territory up to what is now known as the Fairfax Stone, which would place part of present-day West Virginia within its borders. Holmes believed that this evidence should be given more weight than later surveys and agreements between other parties, such as Lord Fairfax and his tenants or even subsequent state legislatures, which he felt were not authorized to alter established boundaries unilaterally. Furthermore, he contended that any ambiguities in these old charters should be resolved by adhering closely to their literal terms rather than trying to infer their authors' intentions based on assumptions about geography or politics at the time they were written.