Strange Things About Jackie Kennedy's Second Marriage We Can't Ignore

When it comes to interesting women, Jackie Kennedy Onassis is toward the top of the list. Born Jacqueline Lee Bouvier, Jackie was only 24 years old when she married John F. Kennedy in September 1953. At the time, Kennedy was a U.S. Senator from Massachusetts, and although he wouldn't become U.S. president until 1961, marrying into the Kennedy family and its legacy was no small affair.

Although the marriage was cut short when JFK was assassinated in November 1963, Jackie did marry a second time, to shipping tycoon Aristotle Onassis in 1968. While neither relationship was perfect — JFK's infidelity plagued Jackie's first marriage — the second marriage was even stranger. Onassis, who was 23 years older than Jackie, forcing us to confront our fixation with age-gap relationships, was at the White House the day of JFK's assassination and allegedly visited Jackie in her room that night. "I can't imagine the grief Jackie was going through," biographer of "Jackie: Public, Private, Secret," J. Randy Taraborrelli told People in June 2023. "I don't think anything happened between them at that moment."

But Onassis being at the White House that night is just the tip of the iceberg regarding the strange details of this marriage. From unconventional living and financial arrangements to Onassis' never-ending love affair with another high-profile woman, there's a lot to unpack with Jackie O.'s second marriage. So much so, that the situation was ultimately a testament to Jackie's will to not just survive, but thrive. 

Although both Jackie and Lee Bouvier came from a well-to-do New York family, when your older sister marries an eventual U.S. president, the dynamic changes a bit. "[John F. Kennedy] and Lee actually got along better than Jackie and JFK," biographer of "Jackie: Public, Private, Secret," J. Randy Taraborrelli told People in June 2023. "And Janet [Bouvier] felt that Jackie [who was four years older than Lee] needed to get settled. Lee did not need to get settled yet." If Lee couldn't be with JFK, she might as well date one of the richest men in the world: Aristotle Onassis.

After the death of Jackie's second son, Patrick, Lee invited Jackie to join her and Onassis on a cruise, hoping to help her sister's mental state. In an excerpt from "Jackie, Janet & Lee: The Secret Lives of Janet Auchincloss and Her Daughters Jacqueline Kennedy Onassis and Lee Radziwill," by author J. Randy Taraborrelli, via Bazaar, a love connection must have been made during that cruise. "I think when Lee looks back on this trip she believes it was the second biggest mistake she ever made," wrote Taraborelli. "The first one being renewing her vows to [Prince Stanislaw Radziwill]."

When Onassis proposed to Jackie five years later, she didn't tell her mother or her sister. When Lee found out, she was devastated and, according to Truman Capote, called him crying, "How could she? How could this happen?"

Despite Aristotle Onassis' wealth and fame, he wanted the world to see him as more than just the international playboy they'd dubbed the "Golden Greek." By marrying Jackie Kennedy, Onassis could do just that. In "Jackie, Janet & Lee: The Secret Lives of Janet Auchincloss and Her Daughters Jacqueline Kennedy Onassis and Lee Radziwill," Jackie's half-brother, Jamie Auchincloss, explained that Onassis' marrying Jackie just made sense.

"Onassis was, in effect, saying to Lee, 'I'm going to be the person whose shoulder Jackie can cry on now. I can provide her with the protection, the security, the love, and the money nobody else can,'" according to an excerpt from the book. Auchincloss explained it wasn't Onassis choosing Jackie over Lee, but thinking beyond that. "I feel it's my duty to help a widow in distress. I also can likely get a lot of mileage out of doing so just in terms of status in the world," Auchincloss said of Onassis' explanation. After all, Onassis scored the ultimate prize in his eyes: the First Lady of the United States.

Although Jackie's Valentino dress is fourth on Women's list of the best wedding dresses from the ladies of the Kennedy family, there was some drama that day. Not only was Radziwill betrayed, but Onassis had another fiancée. When he proposed to Jackie in May 1968, he was already engaged to opera singer Maria Callas, with whom he'd set a November wedding date. 

While it's normal for married couples to occasionally spend time apart or even live together but sleep separately, Jackie Kennedy and Aristotle Onassis had an entire ocean between them most of the time. According to Gill Paul's book, "Jackie and Maria," Jackie spent most of the year in New York City with her children, only visiting Onassis on his private island, Skorpios, in the summer. Even when Onassis went to New York on business, he stayed in a suite at the Pierre Hotel, not with his wife.

As Paul wrote, the two didn't have much in common aside from loving the lavish lifestyle that Onassis' success afforded them. It had also become clear that, despite the suitors that followed after the assassination of John F. Kennedy, Jackie chose the richest, which led to Onassis' daughter, Christina, and son, Alexander, referring to Jackie as a gold digger. But while the money definitely helped keep Jackie and her kids comfortable, she also gained protection in being married to Onassis.

After the murder of Robert F. Kennedy and FBI tips regarding her family's safety, Jackie reportedly said, "They're killing Kennedys; my children are Kennedys." As one of the richest men in the world, Onassis had the type of protection that Jackie would've been looking for at that point in her life. It wasn't just a private island she could frequent when she wanted to, but Onassis had an airline and his own army. 

Not only did Jackie Kennedy marry into Aristotle Onassis' massive wealth, but she ensured she and her children would be comfortably provided for. "She married Aristotle Onassis in part because he was so wealthy that she felt she wouldn't have to worry about money and the physical security of her children," professor of U.S. gender and women's history, Katherine Jellison, told Time in May 2024, adding there was mutual respect and fondness, but 'not a great love story.'

Onassis reportedly gave Jackie a monthly allowance of $30,000, but because she overspent every month, he tried to rein in her spending by dropping it to $20,000. It's worth noting that at this time, in 1969, the median yearly salary per family was $9,400, so Jackie was more than sitting pretty with that $20,000 a month. However, she was a renowned fashion icon and trendsetter, and found a way to make a profit off this arrangement by buying high-end pieces she wore only once or twice, then selling them so she could pocket the money. 

To make things even stranger, when Kennedy married Onassis, their marriage contract included 170 clauses. Not only did it stipulate how much time they'd spend together, but also how much Kennedy would get if Onassis left her, or she him, among other financial details. If Onassis were to leave Kennedy, she'd be entitled to $9.6 million for every year the couple was married.

As if being married to John F. Kennedy and his seemingly endless rotation of mistresses wasn't enough, when Jackie Kennedy met Aristotle Onassis, he had already found the love of his life — and it wasn't Jackie. It was opera singer Maria Callas, whom Onassis met in 1957 and continued to see until his death. "He couldn't live without Maria," personal secretary Kiki Feroudi Moutsatsos told People in November 2024. "Maria was a piece of his soul, of his body, of his brain. That's why they never believed that they could be separate."

But while Jackie knew about JFK's affairs and even supposedly told her sister that she wanted a divorce, this wasn't the case with Onassis. For Jackie, the financial security that came with Onassis far outweighed the fact that her husband was in love with someone else, whom he saw regularly. "Although she knew many things from [Onassis'] behavior, she was pretending that nothing happened," Moutsatsos told the publication.

Although there are many tragedies in this love triangle, Callas' social status was definitely one of the biggest ones. "[Onassis] just wanted to have Jackie Onassis because she was the ultimate trophy wife," a Greek society source told The Standard in April 2012. "He was really in love with Callas, but Callas didn't fulfill the right dynastic requirement. Despite being the world's most famous opera singer, the old Greek families viewed her as a peasant."

Like Jackie, Aristotle Onassis entered into the marriage with two children from a previous relationship: Alexander and Christina Onassis. Unfortunately, neither child would live a full life, with Christina dying in 1988 at 37 from pulmonary edema, and Alexander dying in a plane crash in 1973 when he was 25. But it was the death of Alexander that caused issues within the marriage. Not only did Jackie partially blame herself and the Kennedy curse, but so did Onassis.

By the time Alexander had died in 1973, Onassis was done with Jackie and decided it was time to divorce her for his true love, Maria Callas. But, in deciding that Jackie was the reason behind his problems, including Alexander's death and the mass amount of money that had been flippantly spent, Onassis wanted to make the divorce a public spectacle. "Onassis decided to divorce [Jackie], but only after he had made it as humiliating as possible for her," Arianna Stassinopoulos wrote in "Maria Callas — The Woman Behind the Legend," via UPI. In Onassis' mind, humiliation would not only be payback for the pain that he blamed Jackie for, but would somehow undo the betrayal he felt he had committed against Callas.

Onassis never got the chance to divorce Jackie and ended up dying in 1975. Callas died two years later from a heart attack. After a legal battle with Christina, Jackie walked away with $20 million in 1977.