Andrew Jackson's Biggest Regret As President May Surprise You

Being President of the United States of America isn't an easy job. Tough decisions have to be made, and a president can't always be sure that he's making the right one. Inevitably, heads of state leave office with at least one regret. According to Ranker, George W. Bush regrets starting the Iraq War, something many American citizens decried as a mistake back when it started. Barack Obama regretted his administration's disastrously bungled regime change in Libya.

Bill Clinton's biggest executive office regret wasn't the one you're probably thinking of. He wished he'd have done a better job finding a peaceful solution to the interminable animosity between Israel and Palestine. Considering he's by far not the only one to have failed in that department, we can probably cut him a little slack. And head honcho number 7, Andrew Jackson, also had some strong words of self-reproach after his successor Martin Van Buren was elected. His contrition, however, wasn't as noble as failing to bring peace to a violent part of the world. Jackson's biggest presidential regret will probably surprise you.

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.