Did you know when TR "went west as a cowboy, he went all stops out. He had his spurs and his belt buckles and his pearl-handled revolvers all done for him by Tiffany. He had a woman make him a cowboy shirt with fringe and all that cost $100. Well, that would be $1,000 or $1,500 today. Imagine getting yourself up in a $1,000 cowboy shirt."
I'd have to go with Jackson - all those duels.
Andrew Jackson was the first president on whom an assassination attempt was made. A man named Richard Lawrence approached Jackson with two pistols both of which, for some reason, misfired. With the possibility of an assassination taken off the table, Jackson proceeded to beat Lawrence near death with his cane until Jackson's aides pulled him off the assassin.