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Holy shit.

I know, right? And that's just adolescence. He also fought in the War of 1812 and the First Seminole War and, when he ran out of wars, he just went duel crazy. Jackson's been in 13 duels that we know of. While some historians dispute this number, everyone agrees that he loved him a duel. Every other day, Jackson was out dueling. Dueling this, dueling that. He was one dueling motherfucker.

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Does he have any weaknesses?

In 1806, Andrew Jackson engaged Charles Dickinson in a duel that was chiefly over gambling debts, but also over an insult to Jackson's wife (probably). Though Dickinson was widely known as a good shot, Jackson allowed him to fire first. Dickinson fired, nailed Jackson almost in the heart and started to reload. Before he could finish, Jackson shot him dead. The man plays "Punch-for-Punch" with bullets.

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Sort of sounds like a strength ...

No, no, no, you're thinking about it wrong. While Jackson is indisputably badass, the man does have an ego. If he thinks you're a pussy, he'll get cocky, he'll want to show off. So, as far as strategy goes, you need to act like such a wimp that Jackson, in all of his arrogance, gives you the advantage. Maybe he'll let you shoot first, like Dickinson, or maybe he'll give you two guns, or maybe he'll fight you blindfolded. It all depends on how sure of his victory he is, which all depends on how pathetic you appear as a fighter. Make him believe you're terrified. Whimper, beg to be let out of the fight and, if your threshold for shamelessness is as high as your will to live, see if you can muster up some pants-wetting. Your best bet will be to convince Andrew Jackson that you are a scared little baby who does not want to fight.