When Charles II created the colony of Maryland, he frustrated William Claiborne in particular. Claiborne was a member of the emerging Virginia gentry, and served as Secretary of the Virginia colony on the Governor's Council. His excellent political connections with the General Assembly that met in Jamestown earned him an assignment to explore the upper Chesapeake Bay in the late 1620's. He discovered and "purchased" Kent Island (where the Chesapeake Bay Bridge carries Route 50 to the Eastern Shore), and started to build a successful fur trade there just before the creation of the Maryland colony in 1632.
Suppliers from tribes to the north and west brought him deer hides, as well furs from the Susquehanna and Potomac river valleys. Claiborne offered a better deal than his primary competitors - Swedes who had established a trading post in what today is Delaware. However, Lord Baltimore pushed the Virginia trader off Kent Island, triggering in the end a shooting war between Virginians and Marylanders in the 1630's. A decade later, Claiborne partticipated in an insuurection against the Calverts, forcing the governor to flee. In the 1650's, Claiborne took advantage of the Civil War in England to depose the Calverts again, briefly reclaiming his control of Kent Island until Lord Cromwell restored the Calverts to authority.So when Virginia and Maryland politicians engage in the occasional war of words over Chesapeake Bay cleanup costs, the investments in the regional transportation network, or the extension of water intake pipes into the middle of the Potomac River... it's nothing compared to the good ol' days.