Inside Jackie Kennedy’s Secret Romance With JFK’s Closest Friend


| LAST UPDATE 07/18/2023

By Christiana Holland

Jackie Kennedy was an icon and influenced America immensely as the former First Lady. Yet, it wasn't until years later that we discovered she was involved in a passionate relationship with one of JFK's closest friends.

A Forgotten Love

Jacqueline Kennedy became a household name after marrying JFK, the President of the United States, in 1961, making her the First Lady. While their relationship was in the spotlight, it was also shrouded in secrecy.

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While the press focused on chasing them for inside scoops and stories, it seems they didn't uncover everything. In 2017, the news broke out that an old pile of love letters was found in a Welsh manor and belonged to Jackie. It wasn't long before these letters revealed the secret love affair she had with JFK's trusted advisor.

The Mystery Man

In 1963, just two years into JFK's presidency, he was sadly assassinated while driving through a motorcade in Dallas, Texas. The world was completely shaken up by the breaking news and couldn't help but sympathize with Jackie, who had been his loyal wife for 10 years. However, things took a turn when she found comfort in another man.

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Despite having all eyes on Jackie following her husband's unexpected death, there was no information leaked regarding the relationship. No tabloids, press, or secret paparazzi pictures. So, it would seem the two lived happily ever after in their own world. But this was not the case. Everything was kept a secret... until now.

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A Family Legacy

When the secret love affair became exposed, no one exactly knew how the information got out. Despite the truth always coming out, it is the source behind it that remains a mystery. However, it turned out that the mystery man's grandson spilled the beans after auctioning private and intimate family heirlooms.

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It was a briefcase full of old secrecies. It was astounding to see how old everything was and, particularly, understand why it had been kept all these years. In the pile of possessions, the most prominent giveaway was the puzzling letters. While Jackie married a different man after JFK, it was a mystery how and when the affair began.

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Jackie & Mr. President

The beloved couple was introduced to each other in May 1952. It was instant sparks. At the time, the former first lady was an aspiring photographer for Vogue, capturing every moment she could while John was a congressman. Despite their career differences, their connection was strong, and ultimately, their paths quickly became one.

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Things moved pretty fast, and love was entirely on the cards for both parties. Some say it was love at first sight for John, as he immediately gravitated toward her beauty, intelligence, and passion for life. After a year and a half, the couple exchanged 'I Do's' during a Kennedy Rhode Island reception.

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Introducing The Kennedys

The Kennedys lived a beautiful life together. The tale of a congressman and a photographer went down in the history books. To add even more novelty, JFK decided to run for President. By 1961, John had taken his seat in the Oval Office as the 35th President of the United States, and Jackie adorned her title as the First Lady.

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Jackie had a certain element about her that was hard to pinpoint but more difficult to ignore. She lit up every room while her glamorous and classy fashion reigned throughout First Lady history. She was an elite candidate for the First Lady and inspired multiple television shows, movies, and following her death. The nation adored her.

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November 22nd, 1963

But tragedy struck on November 22nd, 1963. The President, the First Lady, the Texas Governor John Connally, and Connally's wife, Nellie, were riding all together in a vehicle, through Dallas. JFK was locked in as a target and was instantly killed in his vehicle. After 30 minutes of panic, he was pronounced dead and fell onto his wife.

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Despite having police and security surrounding the vehicle, the ambush happened too quickly to take action. However, authorities rushed to his side and arrested the killer, Lee Harvey Oswald, but he was killed shortly after by a local club owner, Jack Ruby. The entire nation mourned his death as Jackie became a widow.

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Nationwide Mourning

Despite Jackie having suffered an incredible amount of PTSD after sitting next to her fallen husband, the attention quickly turned to organizing the funeral. Unfortunately, while the world was shaken up by the situation, they turned to the First Lady as a source of comfort - but she had other plans, focusing on her own well-being.

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The widow had herself and her children to look after. Despite having to put on a brave face for America, this was silently the least of their worries. Ultimately, they had duties to do. Of course, Jackie was offered support, specifically from her late-husband's close friend, the former British ambassador, David Ormsby-Gore.

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Mr. Ormsby-Gore

David Ormsby was a British diplomat and politician formerly known as the 5th Baron Harlech KCMG PC DL. Not to mention, he was highly associated with John F. Kennedy's elite circle of friends. It was a friendship that was built over decades. JFK's father even worked as an ambassador for the U.S. in London during the 30s.

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While JFK's father was closely associated with the British embassy, this allowed their families to grow close over the years. That being said, once Kennedy was elected President, he personally assigned Ormsby-Gore a designated diplomatic role. They worked together through a lot - even during the Cuban Missile Crisis.

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Business & Pleasure

Mr. Kennedy and Ormsby-Gore had a special friendship. He was more like a family member and was even included in government-related issues rather than just international diplomacy. Ormsby-Gore and Kennedy had earned each other's trust. But that being said, Ormsby-Gore had formed a relationship as well with Jackie.

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The relationship remained close throughout Kennedy's presidency. Although, they knew how to carefully handle the friendship to ensure things were kept professionally separate from their personal relations. In 1963, Ormsby-Gore became responsible for banning above-ground weapon tests. And then everything changed.

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Losing More Loved Ones

Jackie was grieving and had very few people she could turn to that she trusted. However, one of those trustees was Ormsby-Gore, who she leaned on for strength. Despite JFK not being around anymore, she owed it to him to maintain a close friendship. Out of mutual respect, they even exchanged gifts over Christmas and birthdays.

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However, things weren't getting any better. Just a few short years after JFK's death, the British diplomat faced a death of his own. In 1967, his wife, Sylvia, was killed in a sudden car crash, leaving behind David and their five kids. Now, David and Jackie had each other to lean on - but it was more than a support system.

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Rising Suspicions

David and Sylvia experienced 27 blissful years of marriage, and unfortunately, both David and Jackie had now experienced the same heartfelt loss. They couldn't believe it had happened to both of them, but in the midst of taking a positive out of a negative, the two had each other and their families.

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It seems there were no relationship boundaries, but in light of both deaths, the press was eager to find out what was happening between the two widows. There were no significant headlines regarding an affair, but years later, a letter leaked where Mrs. Kennedy wrote to Ormsby-Gore, "I would do anything to take that anguish from you."

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A Perfect Match

Nothing regarding a full-blown romance was confirmed, even after the letters. Still, the tabloids released whatever gossip they had. Around ten years ago, The Daily Mail sought insight out of a U.S. tabloid, which claimed that David Ormsby-Gore was "most likely to win Jackie." But that decision was down to Jackie.

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Amid the two losses from both families, David earned a newly inherited title, The Lord Harlech. Considering his father's position, David was awarded a new title and a seat in the British parliament. This instantly made him an elite figure. In hindsight, the former First Lady and an aristocrat sounded like a match made in heaven.

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Fueling the Flames

As soon as the headlines were released, spectators made it their mission to find out what was really going on. How could this be? A romance between the former First Lady and her late husband's close friend was only the most unexpected yet inevitable instance. Still, it would be hard for David to fill the same shoes as JFK.

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People immediately assumed the rumors were true and that the member of the British parliament was going to marry the widowed Kennedy. They were spotted out and about on numerous occasions as well as taking overseas travels together, such as Cambodia. So, it wasn't completely random that the gossip escalated.

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When Kennedy Became Onassis

Despite the rumors, they had vanished fast. To everyone's surprise, Jackie Kennedy had a new man in her arms before we knew it, and it was just a matter of time until she became Jacqueline Kennedy Onassis. She will always be a Kennedy, but she welcomed a new marriage with Aristotle Onassis, a Greek shipping magnate.

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Jackie was seeking love despite Onassis being 23 years older. He was one of the world's wealthiest men at the time, and, for Jackie, he seemed to win her over. Perhaps David was missing something? Or, he was there to fill the void. Regardless, he was reportedly left devastated Jacqueline didn't choose him.

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A Secret Proposal?

The infamous Kennedy-Onassis wedding took place in 1968, and Jackie was no longer Mrs. Kennedy. From that moment, she went by the name Jackie O. While there was no detail surrounding her fling with the aristocrat, it clearly wasn't enough for the former First Lady. Then again, was her significantly older partner making her happy?

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According to The New York Times, Ormsby-Gore did propose to his beloved Jackie. There are even rumors that it happened around the time of their trip to Cambodia or even a few months after. Still, it clearly didn't work out, or she undeniably turned down the aristocrat on one knee. Jaqueline was a powerful woman that knew what she wanted.

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Seeking Answers

While she allegedly turned down Ormsby-Gore, people still wonder what she saw in Onassis just months later, which encouraged her to say yes. For years, people wanted answers, even after both Jackie and David's death. Now, we will never know the full story. Still, the truth always comes out - and it did.

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David Ormsby-Gore passed away in 1985, and his son, Francis, inherited the family estate called Glyn Cywarch. It was a lavish home in Wales that was passed down through the aristocratic generations, including David's grandson Jasset Ormsby-Gore, who is now known as Baron Harlech.

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Family Treasures

The family estate of Glyn Cywarch was not going anywhere any time soon. Even after Baron's grandfather, David, passed, they were certain to keep the home as a historical treasure. Still, substantial renovations had to be made if anyone wanted to live there in one piece. The new owner decided to raise money for the project.

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Jasset gradually began to become more involved in the renovations. He felt the most comfortable looking through old items, gathering them for auctioning, and rearranging everything in time for the renovations. During the process, he came across several leather cases that belonged to David. He had no choice but to look inside.

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Lost Love Letters

Baron, formerly known as Jasset, opened up the cases. He was stunned by the mass of old letters that were exchanged between Jackie and David. He couldn't believe his grandfather kept these letters after all these years - but it was soon clear why. After taking a sneak peek, he found Jackie's response declining his wedding proposal.

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Ormsby-Gore wrote to Jackie expressing his grief over her decline, "All the pathetic plans I had brought with me for visits to Cyrenaica, holidays near one another," and a whole "variety of solutions to our marriage problem… all had become irrelevant trash to be thrown away within a few hours of my landing in New York."

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Revisiting the Past

Baron had opened up a whole case of secrets that were kept for decades upon decades. He had hit the jackpot and hoped these letters would be able to gather proceeds and pay for the renovations. The letters held internal secrets only the two would know about. It was a love affair that was kept quiet for far too long.

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In the same letter where David expressed his anguish, he further admitted to traveling in Cambodia with the in-laws, hinting there would be a secret wedding. He wrote, "As for your photograph, I weep when I look at it… Why do such agonizing things have to happen? Where was the need for it?"

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Another Kennedy Gone

Jackie was certain about not continuing through life as a widow. She wanted to find love again, but unfortunately for David, she was the one that got away. After losing her dearest husband, she lost the second-closest reminder of John - his brother Robert. F Kennedy. Robert died in 1968, also by assassination, heightening the pain.

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In 2017, biographer Barbara Leaming expressed to The New York Times, "It was the second great trauma for her." History then repeated itself. After losing her brother-in-law, instead of turning to her husband, David was on her mind. A month into her new marriage, she imminently sat down on her husband's yacht and wrote to David.

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Unbreakable Bond

The letter was written on November 13th, 1968, just a few weeks after the Onassis-Kennedy wedding. Ultimately, Jacqueline was fighting some sort of feelings for David. She couldn't get him out of her mind, and after losing a close family member, she yearned for the comfort David gave her after losing John.

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However, it turns out Jackie felt stronger feelings than just lonesome comfort. In the letter, she wrote, "We have known so much & shared & lost so much together - Even if it isn't the way you wish now - I hope that bond of love and pain will never be cut." There was a clear connection created that was unlike any other.

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"Not a Man That I Could Marry"

The letter went on, and Jackie had a lot to say. It seemed to be a cry for help as she gushed over David, knowing there was nothing she could truly do about it. She even referred to him as a brother. She wrote, "You are like my beloved brother – and mentor – and the only original spirit I know - as you were to Jack."

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It was a bittersweet moment, as Jackie had to deal with intense feelings toward her late husband's closest friend. She continued, "Please know – you of all people must know it – that we can never really see into the heart of another. You know me. And you must know that the man you write of in your letter is not a man that I could marry."

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Convenient Marriage

According to Barbara Learning, who became Jackie O's biographer, her marriage with Aristotle was "not a marriage out of love." But, everyone apparently was aware of this. On the other hand, Jacqueline became defensive of her husband when Ormsby-Gore suggested Onassis wasn't good enough for her to be her true committed love.

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Jackie wrote to David, "[He] is lonely and wants to protect me from being lonely. And he is wise and kind. Only I can decide if he can, and I decided." While Onassis' wealth was convenient for Jacqueline and her children after losing their father, she believed marrying into the family was a wise move to make.

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Something New

As always, the public became divided on Jackie's dating choices, leaning toward Ormsby-Gore as the better fit. But this was out of the question, as mentioned clearly in her letters. She wrote, "If ever I can find some healing and some comfort – it has to be with somebody who is not part of all my world of past and pain."

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While Jackie highly expressed her clear love for David, she was not in love with him. As the letters went on, it became more apparent why she turned down the proposal. Due to her painful past, she didn't want any ties to her previous relationship. It was time for a fresh start.

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Fresh Start for the Aristocrat

Regarding her marriage, Jackie wrote, "I can find that now… if the world will let us. I know it comes as a surprise to so many people. But they see things for me that I never wanted for myself." Jackie had to put herself and her loved ones first, no matter who she might sadly hurt along the way.

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Jackie and Aristotle remained married until 1975, when Onassis died due to bronchial pneumonia. As anyone would wonder, did Jackie ever go back to David? Though she thought he would always be there, the British ambassador married Pamela Colin in 1969, who had striking similarities to Jacqueline, according to The New York Times.

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Jackie Says Goodbye

Their connection was strong enough to remain as friends despite both having remarried. Of course, rumors still swirled about the two finally coming together. It was like an on-screen romance the public became invested in. However, it was clear Jacqueline married for her children's best interest - and Ormsby couldn't wait forever.

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Still, no one knows what they've lost until it's gone. When David died in a car crash in 1985, Jacqueline, of course, attended the funeral. Whether she regretted turning down the initial proposal or not, the letters proved an inarguable love. We can only imagine how things would have rolled out if the lovers did get hitched...

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Family Ties

After sifting through all the belongings left in the Welsh manor, Lord Harlech collected 18 letters in total. All were beautifully handwritten with so much passion, although 1 letter had been typed. To further highlight the bond between the Kennedys and Ormsby-Gore, there were a few historical belongings that explained a lot.

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One letter wrote, "I appreciate, as you know, in all these critical matters, your judgment – which I have found to be uniformly good and true." Out of the entire collection of letters, it became clear how close the two families were and for how long - especially during the tough moments they fought together.

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Unearthed Documents

The relationship was filled with trust, enough to allow Ormsby-Gore to have access to the White House with a special pass following JFK's assassination. Their relationship was beyond presidential and governmental obligations. That being said, Ormsby-Gore must have seen plenty of other hidden and private documents.

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The New York Times reported another exclusive document was found among the letters. A document was given to David just before Robert Kennedy's funeral, where he was chosen as one of the pallbearers. And another letter was found, but this time, it was written by Jacqueline and regarded a certain upcoming trip...

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Auctioning Off Intimacy

In 2017, decades after the letters were exchanged and found, they went up for sale at Bonhams, an auction house in London. The value of these letters exceeded expectations. However, expert Matthew Haley told The New York Times, "You just don't get this quantity of insight into Jackie's personal life and that level of intimacy."

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In one day, the entire collection had been sold for $123,000. A representative then told NBC News, "When we opened the case, and it's probably the first time the case had been opened in over 30 years, looking down at these handwritten letters, by JFK, by Jackie Kennedy… it was one of sheer amazement really."

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Continuing a Legacy

Considering the timeframe and the level of security, the letters are of dominant value. The letters were bought by a private collector and are kept as a safety net portraying the beautiful bond between Jackie and David. It's no surprise letters that were written by Jacqueline sold for over $120K.

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While we will never know the depth of Jackie and David's relationship, the exchanges of emotion say enough. In hindsight, a written letter says far more than any paparazzi pictures. Learning told The New York Times, "Of course, he fell in love with her – she understood him so well. But I have no idea if it was consummated or not."

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New Revelations

Jack Warnecke, who once dated Jacqueline Kennedy Onassis, talked about a special thing Jackie did every night until she died in May 1994. He said she would take off the string from a pile of envelopes each night, pick a letter from the stack, read it and then burn it.

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The letters were personal notes from people she loved - her kids John and Caroline, her dad Jack Bouvier, her second husband Aristotle Onassis, and even some from Warnecke himself. The pile also had letters from her first husband, JFK, who cheated on her and this really affected Jackie's life.

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An Inside Look

This interesting look into Jackie's life is thanks to J. Randy Taraborrelli, who spent more than ten years talking to people who were really close to her. His chats with family, ex-boyfriends, workers, and pals gave us a better understanding of a woman who, even though she was famous, was very sensitive.

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JFK's many affairs really hurt the First Lady, but there was one incident involving Marilyn Monroe that upset her the most. Friends say that Jackie was really bothered by a phone call Marilyn made to the White House, which Jackie answered on her private line…

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JFK & Marilyn Monroe's Affair

A few weeks before, Jackie had decided not to go to a birthday concert where Monroe, wearing a see-through dress, had sung "Happy Birthday, Mr. President" in a flirty way. When people asked why she didn't go to her husband's party, Jackie said very seriously, "I'm not going to be humiliated."

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When Monroe called the White House asking to speak to JFK, Jackie answered with a cold and quick tone, "What is this about?" People say that Monroe, acting like she did nothing wrong, just replied, "Oh, nothing in particular, I just wanted to say 'hello'."

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An Ongoing Mystery

This phone call bothered Jackie for many, many years. It was only much later, during a therapy meeting, that she found out the call really happened. Her therapist told her that she had also treated Marilyn, who admitted to making the call. This betrayal hurt, and Jackie quickly fired the therapist.

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Jackie has always been a mystery in American history, but behind this public image, she was a woman dealing with personal sadness and heartbreak. But just like the Eternal Flame that burns at JFK's grave, the truth always finds a way to come out. And now, this secret part of her life is finally being shared.

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