Revisiting Marilyn Monroe’s 'scandalous affair' with John F Kennedy and brother, as JFK files await release

US President Donald Trump is set to release classified government documents related to the 1963 assassination of former US President John F. Kennedy on Tuesday. For decades, there have been several conspiracy theories around the assassination of Kennedy and many academic historians are eagerly awaiting the release of these documents to unravel the mystery behind the president's murder.
Trump, who previously signed an executive order directing the federal government to declassify records related to the assassinations of JFK, Robert F. Kennedy, and Martin Luther King Jr., has announced that his administration will make around 80,000 pages of files public.
Kennedy was shot on November 22, 1963 in Dallas, Texas, while he was riding a motorcade with his wife, Jacqueline Kennedy, Texas Governor John Connally, and his wife, Nelly Connally. The group was headed towards a luncheon to the Trade Mart when the tragedy struck.
As new details about the former president’s assassination come to light, we revisit a scandalous chapter from his personal life - his alleged affair with Hollywood icon Marilyn Monroe, and the role his brother reportedly played in making this love triangle even more controversial.

Marilyn Monroe, a cinematic legend and an epitome of beauty died under mysterious circumstances in 1962. Her difficult childhood, struggles with mental health issues, substance abuse, and broken marriages cast a shadow of melancholy over her life. She was rumored to have had affairs with both John F. Kennedy and his brother, Robert Kennedy. It is alleged that her entanglement with the Kennedys may have led to her untimely death, or an orchestrated cover-up of the circumstances surrounding it.

Over the years, multiple sources including biographers and Hollywood insiders, have claimed that Monroe was intimately involved with both Kennedy brothers.

It is said that Monroe's sultry rendition of Happy Birthday to President John F. Kennedy at Madison Square Garden on May 19, 1962 that left the president captivated.
Oscar-winning actress Shirley MacLaine, who was present at an afterparty at the home of Democratic finance chairman Arthur Krim, claims she witnessed both Kennedy brothers engage with Monroe in intimate succession. In her book The Wall of Life, MacLaine recounts that JFK emerged from a bedroom where Monroe had been waiting, only for Robert Kennedy to immediately take his place.
“Jack Kennedy had just walked out of the bedroom behind me, and Bobby Kennedy had just walked in. Marilyn was in the bedroom,” MacLaine writes.
Maureen Callahan, author of Ask Not: The Kennedys and the Women They Destroyed, alleges that Monroe had sex with Robert Kennedy in her dressing room just 30 minutes before taking the stage that night. According to Callahan, Monroe was intoxicated and “flush with the transgressive sex she’d just had with Bobby,” while JFK sat slack-jawed in the audience, fully aware of her growing obsession with his younger brother.

Monroe's twin affair with the Kennedy brothers also became a source of discontentment for her soon. By the summer of 1962, Monroe was reportedly growing desperate, feeling used and discarded by the most powerful family in America. Some sources claim she had even threatened to go public with details of her relationships with both brothers which could have destroyed the political careers of the Kennedy brothers.
James Spada, Monroe’s biographer, stated in 2012, “It was pretty clear that Marilyn had had sexual relations with both Bobby and Jack.” He also noted that actor Peter Lawford, JFK’s brother-in-law, had introduced Monroe to the president in 1954 and later facilitated the handoff to Robert in the spring of 1962.
By the time Monroe was found dead in her Los Angeles home, witnesses claimed that a wiretap had recorded her final, anguished phone calls to Lawford, to JFK, and one final message to Lawford himself: “Say goodbye to Pat. Say goodbye to the president, and say goodbye to yourself because you’re a nice guy.”
It isn't clear whether Monroe's death was suicide, an accidental overdose, or something more sinister, but there is a little doubt that a cover-up followed. Biographers Anthony Summers and Donald Wolfe have pointed out that key figures in Monroe’s inner circle - her housekeeper Eunice Murray, publicist Pat Newcomb, and Lawford, were never thoroughly interrogated by authorities.
Murray in a 1983 interview disclosed that Robert Kennedy had, in fact, been at Monroe's home the night before her death. “Oh, why do I have to keep covering this up?” she said, confirming the affair between Monroe and RFK.
Private investigator Fred Otash's unreleased files, detailed in the 2024 biography The Fixer, reveal that Monroe’s home had been bugged, and that on the day of her death, she confronted Robert Kennedy, accusing him of forcing her to abort his child. According to Otash, RFK left Monroe's house, never intending to return, and Lawford cleaned up any incriminating evidence.
Some remain convinced that Monroe’s death was an act of desperation.
“I think Marilyn Monroe was overwrought about her relationships with both President Kennedy and his brother Robert, felt rejected by both men, had a heated argument with Robert when he visited the house, and then—whether as a cry for help or intending to kill herself—swallowed too many pills,” Summers said in The Mystery of Marilyn Monroe: The Unheard Tapes.
But Joe DiMaggio, Monroe’s second husband, believed the Kennedys were responsible for her death. “The whole lot of Kennedys were lady-killers, and they always got away with it,” he told his biographer. “They’ll be getting away with it a hundred years from now.”