Meet One of JFK's Closest Confidants — Who Proposed to Jackie 4 Years After the Assassination

"They were both second sons of powerful men and they both liked to talk fast and play hard and they both loved politics," author Gary Ginsberg says of David Ormsby-Gore and President Kennedy

John F. Kennedy and David Ormsby-Gore
John F. Kennedy (left) and David Ormsby-Gore. Photo: AP/Shutterstock

David Ormsby-Gore was one of John F. Kennedy's closest confidants, yet not much has been written about the relationship between the 35th president and the British ambassador — who proposed marriage to Jacqueline Kennedy four years after she was widowed.

The bonds between Ormsby-Gore and the Kennedys are explored in a new book, Gary Ginsberg's First Friends: The Powerful Unsung (And Unelected) People Who Shaped Our Presidents.

"There is so much presidential literature, from first wives, from chiefs of staff, even first chefs. But no one has ever looked at the presidency through the lens of the 'first friend': the person who grows closest to the president in a way that a staffer cannot," says Ginsberg, a corporate executive and former Clinton administration official who was also the legal counsel at George, the political magazine launched by Ginsberg's own close friend John F. Kennedy Jr.

"When you see how decisions are made and who has the ear of the president, it's not necessarily the person who has an official post or has been confirmed by the Senate," Ginsberg tells PEOPLE.

In the case of President Kennedy and Ormsby-Gore, the two "bonded instantly" when they first met after Joe Kennedy, the family patriarch, became the U.S. ambassador to the U.K. in the late 1930s. "They were both second sons of powerful men and they both liked to talk fast and play hard and they both loved politics," says Ginsberg.

In the decades following that first meeting, both men also flourished professionally. Ormsby-Gore became the British ambassador to America in the early 1960s at the same time Kennedy was elected to the White House. The former "plays a huge role" for the latter, "intellectually and personally," says Ginsberg. "He is the only one who could move between the political friends, the social friends, the intellectual friends."

John F. Kennedy, Jacqueline Kennedy, Caroline Kennedy, John F. Kennedy Jr., John John, David Ormsby Gore
The Kennedys with David Ormsby-Gore (background). AP/Shutterstock
First Friends The Powerful, Unsung (And Unelected) People Who Shaped Our Presidents by Gary Ginsberg
Twelve Books

Ormsby-Gore also "plays a pivotal role during the Cuban Missile Crisis as British ambassador, although nobody knows it," Ginsberg adds. "And then, at his urging and insistence, he leads Kennedy to pursue the limited Nuclear Test Ban Treaty in 1963, which is the last great bill he passes and which really sets in motion detente — which leads to the end of the Cold War 25 years later."

They men shared a closeness beyond work. "[Ormsby-Gore] and his wife, Sissie, spent more time with JFK and Jackie than any other couple," says Ginsberg, "and Sissie is told by Jackie, the day after the assassination, that, had [their son] Patrick Kennedy lived, she would have been his godmother. But nobody knew this." (Patrick, the Kennedys' youngest son, was born prematurely on Aug. 7, 1963, and lived just three days.)

Ormsby-Gore remained deeply attached to Jackie after the president was assassinated in 1963: In 1967, after his wife died in a car wreck, they traveled together to the temple of Angkor Wat in Cambodia.

The trip was well publicized (and will be the subject of a recently announced Hollywood film, 37 Heavens). But his subsequent proposal of marriage — and her refusal — did not become more widely known to the public until some of their personal correspondence came up for auction in 2017 from a treasure trove of letters found in the home of Ormsby-Gore, who died in 1985.

"He clearly felt very deeply about her," Ginsberg says. "I think she felt deeply about him. They have both suffered grievous losses and he feels like the salve to that is to get married to her. She takes a different view, which is we can't be married because there's just too much pain between us and if we're going to find happiness we have to do it outside of these worlds that we inhabit."

Of her decision to instead marry the shipping tycoon Aristotle Onassis in 1968, Jackie 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. I can find that now — if the world will let us."

In another letter, dated Nov. 13, 1968, she wrote to Ormsby-Gore: "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."

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Jacqueline Kennedy with David Ormsby-Gore
From left: Jacqueline Kennedy with David Ormsby-Gore in 1966. Everett/Shutterstock

Their story is just one of the book's nine portraits of U.S. presidents and the friendships supporting them.

"A 'first friend' has the ability to talk to the president in a way that no one else can," says Ginberg. "It's not necessarily the person with the title or the official post."

"If you look at each president, most of them have somebody in their life who played this kind of unsung role or in some cases was hiding in plain sight," the author tells PEOPLE. "Some were quite public, such as Bebe Rebozo and Richard Nixon; Vernon Jordan and Bill Clinton."

"And with others — such as FDR and Daisy Suckley and Franklin Pierce and Nathaniel Hawthorne — you had to dig for it," Ginsberg says, "and that was the fun of it."

First Friends is on sale now.

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