Alexander Hamilton ($10 guy): Was an elitist dick, was a bad shot, probably did kill (a few) Indians.
Also, he was a homosexual.
Let's not forget the coins:
1c Lincoln: suspension of habeus corpus, killed injuns, etc.
5c Jefferson: slaveowner, flute player, elitist
10c Roosevelt: appeaser of Hitler, Keynesian, helped co-opt a brutal revolt in Spain
25c Washington: slaveowner, injun killer, wearer of wooden teeth
50c Kennedy: elitist, sexually aggressive to the point of a national distraction, warmonger
$1 Eisenhower: his favorite colors were pink and green
We should replace them all with celebrities. I'd go with:
1c: Elvis Presley, the King of Rock and Roll
5c: Michael Jackson, the King of Pop
10c: Howard Stern, the King of all media
25c: Barry Bonds, the Home Run King
50c: Kevin James, the King of Queens
$1: Hank, King of the Hill