Probably the most popular president in both life and death, John Fitzgerald Kennedy was elected president in early 1961 after a tight race against vice president Richard Nixon. Armed with his charismatic personality and an aura that exuded patriotism, Kennedy was and continues to be an American fan-favorite.

After his assassination, his beloved wife Jacqueline “Jackie” Kennedy began to weave the myth of her late husband into America’s memory, forever cementing the fairy-tale legend that was Kennedy. Reality, however, was much different than that fairy tale. It was in that web of myths and legends that the truth behind Kennedy’s scandalous sexual behavior, marital issues and the nature of his assassination was hidden.

If you were to search presidents that had the most money, there is no doubt that he would be on that list. The truth, however, was that Kennedy had very little money of his own and was almost completely dependent on his father, a business mogul and political giant that made his fortunes through running bootleg liquor during Prohibition. When his father’s money ran out or was not enough to meet his fraternity lifestyle, Kennedy needed a new source of income— one he found in his wife, Jackie.

The stepchild of an oil tycoon, Jackie was not without money. She spent much of her youth living lavishly with the wealthy elite, something that appealed to money mongrel Kennedy. Little did he know that when he married her, Jackie had just as much money of her own as Kennedy — almost none. Many speculate that the couple entered their marriage for only economic purposes, each partner eyeing the other’s wealth and power.

The public loved the all-American couple that was John and Jackie Kennedy. A respected and loving husband, a devoted and beautiful wife and doting children, the Kennedy’s exemplified the ideal family. This, however, could not be farther from the truth.

Kennedy was a serial cheater, commonly known for his womanizing tendencies and sexual scandals. His indiscretions nearly ended his relationship in 1956 when he left his very pregnant wife behind to go yachting around Europe with Senator George Smathers. While he was partying in a different continent, Jackie gave birth to a stillborn girl, alone. When Kennedy finally did return, he was greeted with an unreceptive wife, and the two were soon estranged. It was Joe Kennedy, Kennedy’s brother, that actually begged Jackie to return to the marriage, not John.

Probably his most infamous affair was with Marilyn Monroe— the ultimate American sex symbol. Monroe had been tied to the Kennedy family since their emergence on the political scene, as rumors swirled about her affairs with both Joe and John Kennedy. To fuel the ongoing speculation, Monroe appeared before Kennedy in a rhinestone-encrusted, skin-tight dress and famously crooned in her sultry voice, “Happy Birthday, Mr. President.”

It all came to a head when Monroe was found dead in her apartment on Aug. 5, 1962. The scene perfectly fit the stereotypical suicide scene— locked door with an empty bottle of pills laying beside her. The scene, however, raised many questions. Monroe’s alleged relationship with Kennedy has long been seen as the reason for her death. Many speculate that the fear of going public with her affair and her knowledge about confidential information before Kennedy’s reelection campaign served as possible motive for her death.

It was Kennedy’s death on Nov. 22, 1963, that elevated him in martyrdom. His death suppressed all allegations that diminished his character, as that would go against the sainthood that was now seen in him posthumously. With the shot that killed him, all speculation and scandals that accompanied the playboy died as well. The truth will always be buried behind the icon that was John F. Kennedy.