Maryland has always been home to picaroons—the rogues and scoundrels who have shaped history.

Kent Island, home to Blackwater Distilling, was originally founded by William Claiborne, a Virginia trader, in 1631. When the Calvert family was granted a charter by King Charles I to establish the colony of Maryland, the territory of which included Kent Island, Claiborne resisted, insisting the island, then a lucrative trading post, was part of his home colony of Virginia. 

The two groups clashed in a series of naval battles in 1635, including a battle between the Cockatrice of Kent Island and the St. Helen and St. Margaret of Baltimore at the mouth of the Pocomoke River. The Cockatrice was defeated, but the battle did little to settle jurisdiction over the island, which remained in dispute until the founding of the United States of America in 1776.

Centuries later, during the dark years of Prohibition, Marylanders again established themselves as America's original picaroons by becoming the only state not to pass a local law enforcing the national prohibition of alcohol. Maryland thus earned the title of the "wettest state" in the union, and moonshining and rumrunning flourished on the shores of the Chesapeake Bay with its thousands of hidden inlets and coves.

It was during this time that Maryland figures such as Governor Albert Richie and author and Baltimore Sunpapers columnist H.L. Mencken rose to national fame for their vehement opposition to what they viewed as an egregious overreach of Federal authority, and rumrunners like Pete “King James” Kelly rose to infamy.