Of all past United States presidencies, few have the attraction, glamour and intrigue of that of John Fitzgerald Kennedy (JFK). Elected in 1960 and inaugurated on Jan. 20, JFK was both the youngest ever elected to office at the age of 43 and the youngest to be killed in office at 46 years old. He also had a reputation as a bit of a philanderer, with the biggest rumour of an affair tied to legendary actress Marilyn Monroe. Did it really happen?

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The media was a different beast in JFK’s time. It was more respectful of a politicians’ privacy, and while JFK’s dalliances may have been whispered about, they were never publicly brought to light by the news media. This tradition goes all the way back to the Franklin D. Roosevelt years, when the media hid his poor health and wheelchair use, understanding that the president needed to project strength to the world, especially during the second World War.

There is one moment in time widely viewed as the turning point for the media’s turning its blind eye to politicians secret affairs – 1987. At the time, a Colorado Senator named Gary Hart was having an affair with a woman named Donna Rice. The Miami Herald staked him out and confronted him outside of his townhouse in Capitol Hill.

This is widely seen as a turning point in how the media covered a politician’s sex life, but before Hart, politicians could rest easy that the media wasn’t going to out them. This means that JFK pretty much had free reign to go about his salacious business without fear of discovery from the general public.

Who was Marilyn Monroe, and why was she so famous?

Marilyn Monroe is one of the most iconic actresses and models of all time. Since her heyday in the 1950s and ’60s, she’s been an object of fascination by generation after generation. Even as recently as 2023, actress Ana de Armas portrayed the legendary actress in a movie called Blonde.

Monroe was born in Los Angeles in 1926 as Norma Jeane Mortenson. She had a tough upbringing, with a mother who was in and out of mental health asylums, resulting in Monroe having more than ten sets of foster parents. She was even in an orphanage for a short time.

Her beauty was recognized early and by 20 she signed a short-term contract with Twentieth Century-Fox after capturing attention as a popular model for photographers, although the contract was not renewed. She then did a nude calendar photo, which caused a stir and helped her get back into movies.

She got a string of roles starting in 1950 and by 1954 she was one of the most famous women in the world. She married baseball superstar Joe DiMaggio in that year and eventually took on more comedic roles.

In 1962, she famously sang “Happy Birthday” to JFK, and it was around this time they allegedly had their affair. She was dead later that year, presumably by suicide, although there are a number of conspiracy theories surrounding her death.

Did JFK and Marilyn Monroe have an affair?

Monroe’s biographer, James Spada, who wrote the 1982 book Monroe: A Life in Pictures, claims that there was ample evidence that the two American icons had a brief affair. He also claimed she had an affair with JFK’s brother, Robert Kennedy.

 “It was pretty clear that Marilyn had had sexual relations with both Bobby and Jack,” he told People in 2012. The story goes that actor Peter Lawford, known for being a member of the famous “Rat Pack” along with Frank Sinatra and Dean Martin, introduced the two in 1954.

JFK reportedly got tired of Monroe and “passed her off” to his brother in 1962. There are rumors of a tape that corroborates this assumption. Monroe’s house was reportedly bugged and the angry voices of Bobby and Lawford are heard screaming at her during that time period.

In 1983, the BBC did an interview with Eunice Murray, the live-in maid at Monroe’s house in the ’60s. Murray said Monroe admitted that she was tired of having to cover up her affairs with the brothers. Also, people close to Monroe during the investigation were given high-profile government jobs.

Spada alleges there was a Kennedy-related cover up of Monroe’s death, although it didn’t necessarily involve anything as nefarious as her being killed.

“The Kennedys could not risk this coming out because it could have brought down the president. But the cover-up that was designed to prevent anyone from finding out that Marilyn was involved intimately with the Kennedy family has been misinterpreted as a cover-up of their having murdered her,” Spada said. 

However, Sinatra’s former road manager, Tony Oppedisano, said the reason the affair didn’t come out was much more straightforward – she “wasn’t about to break up the president’s marriage, so she wouldn’t let it go that far, even if she felt that deeply.”

Others commented on Monroe’s instability as a reason she became a threat to JFK. DiMaggio also commented on the purported affair, calling the Kennedys “lady-killers” who “always got away with it.”

“‘I always knew who killed her, but I didn’t want to start a revolution in this country. She told me someone would do her in, but I kept quiet,'” DiMaggio said in a book called Dinner with DiMaggio: Memories of an American Hero, written by John Positano.

Positano would later say that DiMaggio meant the Kennedys put Marilyn in a position that wasn’t great for her mental health, and that he didn’t think they were good people for her to be around. In a 2022 documentary about Monroe called The Mystery of Marilyn Monroe: The Unheard Tapes, Robert Kennedy allegedly visited Monroe’s house mere hours before she died, to end their affair.

Investigative journalist Anthony Summers said that even though we might never know the true circumstances behind Monroe’s death, it was pretty clear that her passing had been “deliberately covered up,” and that happened “because of her connection to the Kennedy brothers.”

Where does that leave us? Right back where we started, in speculation mode. All the evidence points to the fact that she did indeed have affairs with both Kennedy brothers, even if there is no concrete evidence of such.

Had the affairs happened in another time, it’s very possible that the media may have dug in and tried to find hardline evidence of the affair. However, in that era, that just wasn’t the case.