The day after Van Buren was elected in 1836, Jackson was hanging out with a friend, ruminating on his time in office. When his friend asked him if he had any regrets, his response was sensational enough to go on to warrant a spot in the 2012 humor book “Crazy S*** Presidents Said: The Most Surprising, Shocking, and Stupid Statements from George Washington to Barack Obama.” Jackson’s biggest regret was not finishing off his hated rivals. “I didn’t shoot Henry Clay and I didn’t hang John C. Calhoun,” he told his friend.

Most presidents kill enough people while in office to rack up a good amount of remorse by the time they return to civilian life, but Andrew Jackson was no such head of state. And another moment from his life shows that such language wasn’t mere posturing or braggadocio. As biographer Jon Meacham noted in his Pulitzer Prize-winning 2008 book about Jackson’s presidency “American Lion,” the seventh U.S. president once won a duel in 1806 after first taking a bullet to the chest himself. He later told a friend that nothing would have stopped him from killing Charles Dickinson, with whom he had a dispute over a horse race. “If he had shot me through the brain, sir,” Jackson said, “I should still have killed him.” Now that’s the kind of person whose face you want on the $20 bill.