Lifting the Lid on Jackie Kennedy’s Secret Romance With a Former Friend of the President


| LAST UPDATE 07/16/2023

By Lily Tipton

Former First Lady Jackie Kennedy was almost as much in the spotlight as her husband, President John F. Kennedy. But following her husband's assassination, she embarked on a hidden romance that was kept under wraps for decades...

A Classified Relationship

Everyone is familiar with the love shared between Jacqueline Kennedy Onassis and President John F. Kennedy. What's less known is the relationship entanglements that went on behind the scenes.

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It was not until 2017 that this secret romance was exposed to the public when a collection of love letters were uncovered in a Welsh mansion. In these documents, words of love and friendship were exchanged between Jackie and her late husband's right-hand man...

Another Man's Arms

The assassination of John F. Kennedy in 1963 hit the nation hard. His wife, Jackie Kennedy, understandably was the most heartbroken after having been married to the man for ten happy years. When he passed prematurely, the former First Lady was devastated, seeking solace in the arms of another man.

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At this time, the man in question's identity was kept a secret from the rest of the world, only for it to sizzle out before there was something more to tell. Considering the high-profile woman involved in this love affair, it's remarkable how it was able to stay under the radar - until 2017, that is.

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Revealing Letters

Just a few years back, the world was informed of the secret affair between Mrs. Kennedy and her ex-lover, one which had been a well-kept secret for many years. The truth began to unravel when Jackie's ex-partner's grandson discovered some old family documents in the attic.

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While all the heirlooms found were of significant historical value, it was one pile of documents that exposed Jackie Kennedy's greatest secret. It was a collection of letters exchanged between the former First Lady and her husband's most trusted advisor. She had remarried after JFK's death, but this was someone else...

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Crossing Paths

Although her name is now synonymous with presidential royalty, Jackie Kennedy was once a thriving photographer. She was Vogue magazine's in-house photographer when she first crossed paths with then Congressman John F. Kennedy in May 1952. Like a true love story, the pair fell fast in love.

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JFK was taken aback by Jackie's overwhelming beauty, charm, and intelligence. Just a year and a half after their first meeting, the congressman bent down on one knee and asked her to be his wife. Everyone who mattered was in attendance at their Rhode Island wedding.

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The First Couple

A few years after becoming a married man, JFK announced his presidential campaign to the nation. In 1961, he was declared the 35th President of the United States. Jackie immediately rose to the challenge of being his First Lady, taking on the role with grace and dignity.

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There was nothing not to adore about Jackie Kennedy. She stole the hearts of the nation with each public event she attended and with each fashionable outfit she wore. She was a woman of the people and a true natural leader. For many years after her reign, movies and documentaries were made in her honor.

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A Fateful Drive

Then, on November 22, 1963, tragedy struck. The Kennedy dream was shattered after the President was shot while driving in an open-air motorcade through the streets of Texas. Upon impact, he fell onto his wife, Jackie, who sat beside him. Just thirty minutes later, news arrived that the President had been killed.

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Although the man responsible for the crime, Lee Harvey Oswald, was immediately arrested, he was soon shot by local nightclub owner Jack Ruby. The country was in great pain following the death of their leader, most of all the woman he left behind. It's believed Jackie struggled with PTSD in the aftermath of the loss.

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Paying Respects

With the whole country struggling to make sense of the recent events, they looked to the First Lady for guidance and strength. Jackie Kennedy was a born leader, managing to put her heartbreak aside and focus her efforts on her late husband's funeral arrangements.

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Despite the funeral ceremony being heart-wrenching and painful, Jackie and the Kennedy children put on a strong front, walking in front of the cameras with composed expressions. Behind the scenes, Jackie was spiraling from the pain, and she found support from an unexpected source - her late husband's #1 man, David Ormsby-Gore.

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Right-Hand Man

David Ormsby was everything to John F. Kennedy. His closest friend, his British ambassador, and a supportive politician and diplomat, he was considered by JFK to be one of his best friends. It was a decades-long relationship that dated back to the '30s when JFK's father worked in London as an ambassador for the U.S.

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In the years following, the Kennedy and Ormsby-Gore families grew closer. So, when JFK became President, it was a no-brainer that he would appoint Ormsby-Gore as his own British ambassador. The two became close friends and relied on each other for advice, as demonstrated during the Cuban Missile Crisis.

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Strictly Business

JFK and Ormsby-Gore's close relationship meant that the President treated his ambassador like more than just a foreign diplomat, allowing him into his close government circle. He highly valued his opinions on a variety of issues, and this could be the reason Jackie was drawn to him in her time of mourning.

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Throughout his years as President of the United States, he remained close with Ormsby-Gore on personal and professional matters. Gore had been one of the main men behind the above-ground weapon testing ban in 1963. This was also the year that JFK was assassinated.

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Tragedy Hits Again

As the country reeled from the news of the President's car shooting, Jackie turned to the man who had always been closest to her husband, David Ormsby-Gore. The assassination took their previously civil relationship to a new friendship level, and they exchanged gifts on holidays and birthdays.

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Just four years after losing his best friend and confidant, David suffered another tragic loss when his wife Sylvia was killed in a car crash in 1967. Just like Jackie, he had been left all alone to care for the children she was forced to leave behind.

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Increased Suspicions

Bonding over their mutual experience and pain, Kennedy and Ormsby-Gore continued to grow closer and closer. With all that he had done for her in the aftermath of JFK's death, Jackie felt compelled to help him through the passing of his wife of 27 years.

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During these years, post-Sylvia's death, rumors began to spread in regard to the true nature of their relationship. Multiple media outlets speculated the pair were romantically involved. In the recently discovered letters, Jackie was found to have written to her widowed friend, "I would do anything to take that anguish from you."

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The Most Eligible

Despite the increased pressure from the media, Mrs. Kennedy and Ormsby-Gore kept their lips sealed, neither confirming nor denying the romance rumors. Decades later, the Daily Mail uncovered a US tabloid that stated David was the guy "most likely to win Jackie."

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Supporting this claim of David's eligibility was his new name, The Lord Harlech, which was bestowed upon him by his father. This updated aristocratic title earned him a place in the British parliament, taking his social status to new heights. With this in mind, who would be better suited for the highly esteemed Mrs. Kennedy?

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Fact or Fiction?

The question on everyone's lips was who would take JFK's place and be the next man on Jackie Kennedy's arm. The former First Lady was a force, so not just any man would fit the bill. JFK had been her great love, so the next man in line would need to live up to his name and be of equal status.

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For the first few years post President Kennedy's death, it appeared as if Ormsby-Gore was indeed the next guy for Jackie Kennedy. They were often photographed together around the country and were even spotted traveling abroad to Cambodia, where they admired Angkor Wat side by side.

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Marrying Aristotle

To everyone's surprise, Ormsby-Gore did not become Mrs. Kennedy's next husband. Instead, she married Aristotle Onassis, becoming Jacqueline Kennedy Onassis. Her new husband may have been 23 years older than her, but his successful Greek shipping empire meant he was well within her ranks.

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Although no one had seen it coming, Jackie Kennedy accepted the billionaire's marriage proposal, and the two wed shortly after. From the outsider's perspective, it seemed to be a mismatched partnership, particularly due to the age difference. It's believed that Lord Harlech was left reeling from the news.

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Becoming Jackie O

After making things official with Aristotle, Jackie Kennedy went by her new name, "Jackie O." While before she had been the widowed, rumored love interest of Ormsby-Gore, she had now risen to be one-half of a billionaire empire. Was she as happy as she seemed?

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As The New York Times reported, there was some unfinished business regarding her relationship with David. It's believed the ex-ambassador proposed to Jackie prior to her marrying Onassis, perhaps during their Cambodia adventure. It goes without saying that she did not accept...

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Digging Deeper

Looking back on this period of time, many questions arise. What had been behind Jackie's decision to reject her best friend and supporter, Ormby-Gore? More importantly, why had she decided to marry Onassis so shortly after she turned him down? The complicated tale of Jackie and David stayed secret for decades - until now.

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After David Ormsby-Gore passed in 1985, his Glyyn Cywarch estate in Wales was inherited by his son Francis. After he died in 2016, the estate was passed down again and put in the name of David's grandson Jasset Ormsby-Gore, A.K.A Baron Harlech.

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Promising Findings

When Baron received the estate, he was disappointed to see it had not been well-kept and the interior design was in need of some modernization. Deciding to renovate the mansion, he drew up a financial plan to raise the necessary funds for completion.

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Understanding his grandfather's role in President Kennedy's presidential ruling, he reckoned there would be some valuable family treasures within the estate. While searching for items he could auction off, he came across a small collection of leather cases in his grandfather's name. Baron's curiosity was piqued...

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Heartfelt Correspondance

Breaking the locks to open the cases, Baron began to rummage through their contents. To his surprise, he found a series of handwritten letters exchanged between Mrs. Kennedy and his grandfather David. After reading through a few, he found one written shortly after Jackie rejected Ormsy-Gore's hand in marriage.

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In the letter, David wrote about his heartbreak. He penned, "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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Heartbreaking Details

As far as Baron was concerned, he had more than enough inventory to finance his mansion renovation. These letters alone would be of incredible value and highly sought after because they contained information that was kept from the public for many years.

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Not only did this correspondence prove that Jackie and David shared a forbidden love, but it also revealed his great desire to marry her. "As for your photograph, I weep when I look at it," his letter read. "Why do such agonizing things have to happen? Where was the need for it?"

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Tragedy, Again

In an effort to live out her life as more than just a "widow," Jackie made the decision to marry the ever-successful Mr. Onassis. However, when tragedy struck the Kennedy family yet again, it wasn't with her husband who Jackie found comfort. Like last time, it was Ormsby-Gore.

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In June 1968, the late President's brother, Robert F. Kennedy, was also killed. Jackie, alongside the rest of the family, was left in shock. As noted by biographer Barbara Leaming, "It was the second great trauma for her." Instead of turning to her husband in this time of need, she sat down and wrote to David.

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Dear, Old Friend

On November 13, 1968, mere weeks after exchanging vows with Aristotle, she wrote a letter to her friend David. When she should have been in a period of newlywed bliss, her mind was focused on David Ormsby-Gore, who she longed to be with at this time.

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The newly named "Jackie O" opened up to David in this letter, revealing her true feelings about their friendship. "We have known so much & shared & lost so much together," she wrote. "Even if it isn't the way you wish now - I hope that bond of love and pain will never be cut."

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"My Beloved Brother"

After spilling her feelings for a number of pages, she delivered the line that no man wants to hear in an effort to explain why she believed they could never have married. "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 heartbreaking for her to pen this letter, but she understood it was a necessity. "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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A Tactical Arrangement

Mrs. Kennedy's biographer Barbara Learning noted that the former First Lady's relationship with Onassis was evidently "not a marriage of love." Although this was a fact known by most at the time, Jackie still defended her Aristotle when Ormsby-Gore questioned his worthiness in marrying her.

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"[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," she explained in her letter to Ormsby-Gore. She had done her calculations and understood that marrying him and his fortunes would be a smart business move for her and her family.

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A New Chapter

In response to the public backlash against her marriage to Onassis and her rejection of the suitable Ormsby-Gore, Jackie explained her reasoning in writing. "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," she wrote.

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One look through these letters, and it's abundantly clear that Jackie loved and cared for her good friend David. Whether she was in love with him was another question, as it seems she had strong reasoning for rejecting his marriage proposal and taking her life in a new direction with Onassis.

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Moving Forward

"I can find that now," the new Jackie O continued in reference to her new relationship, "if the world will let us." Continuing her thoughts, she wrote, "I know it comes as a surprise to so many people. But they see things for me that I never wanted for myself." Jackie O had her mind made up.

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Despite all the criticisms, Mr. and Mrs. Onassis remained unified until Aristotle's death from bronchial pneumonia in 1975. During this time, David finally managed to move on from his love for Jackie, marrying Pamela Colin in 1969. According to The New York Times, she bore a striking resemblance to the former First Lady.

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Feelings of Regret?

Although they both moved on from each other and formed new lives with new partners, Jackie and Ormsby-Gore remained close friends through it all. Ignoring all the claims that they were meant to be, Jackie chose a path of financial security, and Ormsby sought companionship elsewhere.

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In 1985, the British ambassador was killed in a car accident, and his former best friend, Jackie O, attended his funeral. As she stood there, paying her respects, many began to speculate whether she was experiencing feelings of regret over not marrying him. Regardless, the letters proved they shared a deep love on some level.

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Connected Families

Gathering up all the documents and belongings together, Baron calculated a total of 18 letters exchanged between his grandfather and the former First Lady. While perhaps less lucrative, he was also excited to discover papers that demonstrated how close the Kennedy and Ormsby-Gore families were.

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"I appreciate, as you know, in all these critical matters, your judgment – which I have found to be uniformly good and true," one letter read. These letters and documents dating back to the '30s track the progression of their developing family bond as well as the more difficult times along the way.

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Additional Findings

In addition to all of the above, a special White House pass was discovered, which had been given to Ormsby-Gore after the death of John F. Kennedy. This, perhaps more than the rest, demonstrated how deep their relationship was, more than just diplomatic partners.

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Another interesting finding, reported by The New York Times, was a document given to David Ormsby-Gore just before the funeral of the former President's brother. There was additionally a letter written by an intoxicated Mrs. Kennedy who wrote extensively about her upcoming travels.

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The Highest Bidder

In 2017, this prestigious and historical collection was finally put up for auction at Bonhams in London. Considering its salacious contents, demand was high, and the prices were set to reflect that. "You just don't get this quantity of insight into Jackie's personal life and that level of intimacy," explained expert Matthew Haley.

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Just one day into the sale, the belongings went for a staggering $123,000. A Bonham's representative said to 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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An Iconic Legacy

The man behind the purchase had been a private collector who kept the collection of letters safe as a historical momentum. The final price of over $120,000 is hardly surprising considering the iconic status of the woman behind them. It was a truly rare and revealing discovery.

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Although the letters give us great insight into the nature of Jackie and David's relationship, there is likely more to their love story than we will ever know. As Learning noted to 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 Discoveries

The letters were intimate missives from loved ones - her children John and Caroline, her father Jack Bouvier, her second husband Aristotle Onassis, and even a few from Warnecke himself. The collection also included letters from her first husband, JFK, whose infidelities cast a long shadow over Jackie's life.

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These weren't just any letters - they were heartfelt messages from the people she loved most - her kids John and Caroline, her dad Jack Bouvier, her second husband Aristotle Onassis, and even a few from Warnecke himself. THere were also letters from JFK, whose cheating ways always seemed to hang over Jackie's life like a dark cloud.

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The People Close to Jackie

This fascinating peek into Jackie's life is thanks to J. Randy Taraborrelli, who spent more than ten years chatting with the people who knew Jackie best. His heart-to-heart talks with family, ex-lovers, staff, and buddies revealed a side of Jackie that, despite her public image, was incredibly sensitive.

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Haunted by JFK's countless affairs, there was one episode involving Marilyn Monroe that really messed with Jackie. Her friends say that Jackie was really shaken up by a phone call Marilyn made to the White House, which ended up ringing on Jackie's private line...

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His Affair With Marilyn Monroe

A few weeks before, Jackie had passed on going to a birthday concert where Monroe, wearing a see-through dress, had famously sung, "Happy Birthday, Mr. President." When quizzed about why she decided to skip her hubby's bash, Jackie didn't mince words, saying, "I'm not going to be humiliated."

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When Monroe had previously called the White House asking for JFK, Jackie responded with a cool and somewhat curt tone, "What is this about?" Monroe, acting all innocent, apparently responded with, "Oh, nothing in particular, I just wanted to say 'hello'."

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A Longstanding Mystery

This episode stuck with Jackie for a long, long time. It was only years later, during a therapy appointment, that she found out the call wasn't some cruel joke. Her shrink let slip that she'd been treating Marilyn, who admitted to making the call. Feeling betrayed, Jackie immediately gave the therapist the boot.

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Jackie has always been a mystery in the eyes of the world. But behind all the public glitz, she was just a woman dealing with her own private sorrows. Just like the Eternal Flame that burnsg at JFK's grave, the truth has a knack for coming out. And now, this secret part of her life is finally getting its moment in the spotlight.

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