John F. Kennedy
(Cecil Stoughton, AP/Bonhams)
President John F. Kennedy, a Massachusetts Democrat, was another politician accused of conducting multiple affairs, most notably with actress Marilyn Monroe. Monroe famously sang "Happy Birthday" to Kennedy during a New York fundraiser, which helped fuel the rumors. His wife, Jackie, also allegedly conducted affairs with men in retaliation, while the couple occupied the White House. The couple was also rumored to be reconciling just before Kennedy's 1963 assassination.