John Breckinridge
Voted into office as James Buchanan's Vice President at the tender age of 36, John Cabell Breckinridge is still the youngest person ever to hold the office. And before he became the only one ever forced to flee the country to escape charges of treason, Breckinridge was actually a pretty popular VP: so impressed was Kentucky's legislature that they elected him to the U.S. Senate a year and a half before his vice presidential term ended.
After a failed bid for the Presidency in the tumultuous 1860 elections (eventually won by Abraham Lincoln), Breckinridge returned to Kentucky, urging the state to secede at the outbreak of the Civil War. But Kentucky stayed in the Union, prompting Breckinridge to quit the Senate and sign up for the Confederate Army. Because his state hadn't joined the Confederacy, however, his new brothers-in-arms viewed the former Senator with suspicion and immediately charged him with treason. Towards the end of the war, he managed to flee to Florida, where he borrowed a small boat. Breckinridge's ill luck held: the boat was attacked by pirates, and when he managed to escape in a dinghy, a storm blew away the mast, leaving him bobbing along in the Caribbean for three weeks, eventually washing up in Cuba. (As the story goes, a Cuban band played The Star Spangled Banner and Yankee Doodle at his welcoming ceremony — song choices Breckinridge did not appreciate.) He eventually escaped to Europe, from whence he refused to return until President Andrew Johnson granted him amnesty in 1868. But it wasn't until a century later that a federal judge in Kentucky officially dismissed the treason charges against him. The town of Breckenridge, Colorado is named in his honor — although it altered the spelling of its name after the Civil War, so as not to be associated with a traitor.
—Claire Suddath