Secretary of the Ladies
Alexander Hamilton had a ruddy face, freckles, sandy hair and eyes that were described as flashing violet-blue. His looks certainly worked on the women. When he got caught up in a love affair with Maria Reynolds, Hamilton paid blackmail money to her husband to continue sleeping with her. But then Maria's husband tried to claim that Hamilton was using state funds to pay Maria for her services. (A Congressional investigation said he wasn't.) Later, Hamilton began a long-term love affair with his sister-in-law. Though his honesty about his sexual shenanigans is still rare among politicians, it is believed that his public peccadilloes ultimately cost him the presidency.