John F. Kennedy (JFK) is often remembered as one of America’s greatest presidents, and his life story has been retold countless times. From his privileged upbringing to his tragic assassination, Kennedy’s biography is one of the most familiar in modern history.

But much of what we read about JFK focuses on his time in the White House, his marriage to Jackie Kennedy, or his rumored affair with Marilyn Monroe. In reality, Kennedy’s life before the presidency was just as extraordinary—if not more so. He was a war hero, a best-selling author, and a notorious playboy long before entering politics.

Here are some of the most unusual and surprising facts about John F. Kennedy that you probably haven’t heard before.

One of His Girlfriends Had Close Ties to Hitler

Kennedy’s reputation as a ladies’ man is legendary, but one of his early relationships is particularly striking. While serving in the Navy at age 20, JFK fell for Inga Arvad, a Danish beauty queen-turned-journalist.

Years earlier, Arvad had interviewed Adolf Hitler, who was so taken with her that he invited her as his guest to the 1936 Berlin Olympics. He reportedly referred to her as the perfect example of “Nordic beauty.” While there’s no evidence that she and Hitler had an affair, the idea that Kennedy and Hitler may have shared the same romantic partner is a strange twist of history.

A Lifetime of Health Struggles

Kennedy’s youthful looks and charisma masked a life of chronic illness. He suffered from Addison’s disease and hypothyroidism, both of which left him in near-constant pain.

To cope, he underwent a wide range of treatments—including steroids, animal hormones, and even amphetamines. Despite these challenges, he managed to maintain the confident, vibrant public image that helped propel him to the presidency.

Woody Harrelson’s Father Claimed to Have Killed Him

The assassination of JFK remains one of the most analyzed events in American history, and countless conspiracy theories surround it. One of the strangest involves Charles V. Harrelson, father of actor Woody Harrelson.

While serving a prison sentence for another murder, Charles repeatedly claimed that he had been involved in Kennedy’s assassination. His confessions were never taken seriously, but they added another layer of intrigue to one of the world’s most famous unsolved crimes.

He Nearly Died Several Times Before Becoming President

Long before his assassination, Kennedy came close to death on at least three occasions. Twice he received the Catholic last rites because of complications from Addison’s disease, and once after slipping into a coma following spinal surgery in 1954.

These near-death experiences were hidden from the public until long after his death, preserving his image as a vigorous young leader.

A Pulitzer Prize-Winning Author

Kennedy’s ambitions weren’t limited to politics. At just 22, he published his first book, based on his Harvard thesis. Later, as a journalist, he covered the final months of World War II.

In 1957, he won the Pulitzer Prize for his book Profiles in Courage. Although there was some debate over how much of it he personally wrote, the award solidified his reputation as a serious thinker.

Stockpiling Cigars Before Banning Them

Kennedy’s presidency is remembered for tense moments with Cuba, including the Bay of Pigs and the Cuban Missile Crisis. Yet one of his more ironic moves came just before signing the trade embargo against Cuba—he ordered over 1,200 Cuban cigars for his private stash.

A Historic Inaugural Ball

As America’s first Catholic president, Kennedy’s inauguration was already historic. At the ball, he made history again by becoming the first president to publicly dance with Black women—a progressive gesture at the time, though it also reflected his well-known love of women in general.

Rejected From the Military—At First

Given his health problems, Kennedy could have easily avoided World War II. In fact, the military initially rejected him. But with help from his father’s political connections, he joined the Navy and was eventually put in command of a patrol torpedo boat.

When his boat was rammed and sunk by a Japanese destroyer, Kennedy led his crew to safety, even towing a badly injured sailor to shore by holding the man’s life vest strap in his teeth. He was later awarded the Purple Heart and returned to active duty despite his injuries.

He Donated His Salary to Charity

While many politicians boast about giving up their salaries, Kennedy quietly lived by it. Coming from wealth, he didn’t need the paycheck, so he donated his congressional and presidential salaries to charity throughout his career.

At the time, he was the wealthiest man ever elected president, yet he ensured he personally profited nothing from the office.

Larry King Once Crashed Into His Car

Talk show legend Larry King liked to tell the story of the day he rear-ended JFK’s car in the 1950s, when Kennedy was still a senator.

No one was injured, but Kennedy scolded the young driver before letting him off the hook—with one condition: that King would vote for him if he ever ran for president. King claimed he kept that promise.

Secret White House Recordings

Richard Nixon is infamous for the secret recordings that led to his downfall, but JFK actually started the practice years earlier. Kennedy had the Oval Office wired so he could record conversations, intending to use them later for his memoirs.

These tapes, especially from the Cuban Missile Crisis, have since become invaluable historical records.

A Mountain in Canada Bears His Name

Kennedy’s legacy extends beyond politics and into geography. After his assassination, Canada named a newly surveyed mountain in Yukon’s Kluane National Park in his honor.

In a poignant tribute, Robert Kennedy, JFK’s younger brother, became the first person to climb Mount Kennedy in 1965.

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Final Thoughts

John F. Kennedy’s life was far richer and stranger than the polished image often shown in history books. From his brushes with death and health struggles to his secret generosity and unusual love life, Kennedy’s story is filled with fascinating details that go far beyond the presidency.