6) Alexander Hamilton
Pros: Most remembered these days for losing to Aaron Burr in a duel and for being on the $10 bill, Hamilton was basically the founder of our financial system. He assisted Madison (and John Jay) with the writing of The Federalist Papers and the Constitution. Were he not born in the Caribbean, he almost certainly would have been president after Jefferson (with whom he disagreed passionately).
Cons: Seems to have been a bit of an abrasive character. Might have started nasty rumors (assuming they were untrue) that lead to the Burr duel.
