Edward Shippen III, born July 9, 1703 in Boston, Massachusetts, is the oldest relative I know of. However, I only encountered him by searching someone I actually had heard of on Wikipedia: Margaret Shippen. Called Peggy Arnold by her friends, she was the wife of Benedict Arnold, the man colloquially known as the greatest traitor in the history of the Revolutionary War. Benedict, an acquaintance of George Washington and other revolutionary leaders, ran the fort at West Point as a general after leading troops into battle at Fort Ticonderoga and suffering a debilitating leg injury (this sacrifice contributed greatly to his respect among the revolutionary leaders). He sold the plans of the fort, the locations of armaments, and other war secrets to the British. When the Americans caught wind of Arnold’s plot, Peggy and Benedict were long gone.
Peggy was paid 350 pound for her contributions, which included “through her unceasing perseverance, ultimately [bringing] the general [Benedict] into an arrangement to surrender West Point.” Peggy herself was “disgusted with the American cause” and felt at home in London, where the two lived the remainder of their lives. (Randall, Willard Sterne (1990). Benedict Arnold: Patriot and Traitor. William Morrow and Inc.)
A ranking from http://history.howstuffworks.com/historical-figures/10-history-notorious-traitors.htm#page=3 ranks Benedict Arnold third among the top ten most notorious traitors of all time — two spots behind Cassius and Brutus and one behind Judas Iscariot. Yeah, that Judas. Arnold’s life is well documented, and his ranking is supported by biographical information from Creighton University and a few prominent biographers, including Aaron Burr, who later went on to become the third Vice President of the US. All these sources attribute Margaret Shippen with convincing Benedict to betray the US.
I have met no one in my family who feels disgraced to be related to Margaret Shippen; my grandmother argues that Benedict felt that Britain would have provided a better life for the colonists, and that’s why he switched sides. As a matter of fact, my aunt, Peggy Shippen, uses the story behind her name as an ice breaker — a really freakin’ good one. Fortunately, the Shippen name is not totally besmirched, as there is a town in Pennsylvania named Shippensburg, and many honorable judges and lawyers also bore the name in the following centuries. Though I only use Shippen as my middle name, I am a proud member of the Shippen family — for better or for worse.