One of Winston Churchill’s least-remembered meetings, more fleeting than historic, took place when Senator John F. Kennedy and his wife, Jacqueline, boarded the giant pleasure yacht of Greek tycoon Aristotle Onassis in 1958.

As a young man, JFK had greatly admired the former British prime minister. Churchill’s views of the world and use of power and words had so inspired his own. Jack looked forward to a face-to-face meeting with the great man himself.

“He admired Churchill and wanted to meet him,” recalled Jacqueline of her husband’s anticipation.

By 1958, Senator Kennedy’s much-publicized chance to become the next president had stirred Churchill’s interest. Not only had he followed American politics for a long time, but there seemed a natural curiosity about the son of his onetime critic, Joseph Kennedy, now rising to the top. When he heard that the young senator and his wife were visiting Joe and Rose on vacation along the Mediterranean, Churchill decided to extend an invitation.

“They tell me he is presidential timber,” Churchill explained to his host, Onassis. “I’d like to meet this presidential timber.”

Jackie shared her husband’s enthusiasm as they anxiously entered Onassis’s yacht to join an awaiting Churchill. Ten years earlier, while on a European trip as a Vassar student, she was invited to a garden party at Buckingham Palace, and shook Churchill’s hand, twice. Like a schoolgirl, she ran back to the end of the reception line after her first handshake so she could shake his hand again.

Once aboard, Jack was ushered on a path to Churchill, while the magnanimous host, Onassis, showed Jackie around his massive yacht.

Using guile and skill, Onassis had built an armada of tankers and freighters to service his oil-rich Saudi Arabian clients and a world hungry for petroleum. The rootless shipping magnate likened himself to Odysseus, the mariner of Greek mythology. With silver hair and a jackal’s smile, Onassis charmed men and seduced women, most famously the opera singer Maria Callas.

On his yacht, the bar stools were covered with whale foreskin, allowing him crudely to tell female guests such as Greta Garbo that they were “sitting on the biggest penis in the world.” From his base in Monte Carlo, selected for its tax-free status rather than any national fidelity, he spent lavishly on anything he desired. “They say I have no class,” he explained. “Fortunately people with class are usually willing to overlook this flaw because I am very rich.”

On her tour, Jackie seemed delighted when she inspected one of the rooms with a huge kidney-shaped bathtub. “Why, it’s large enough for a carrier of the Forrestal class!” she exclaimed, displaying her own nautical knowledge. On this evening, Jackie wore a white Yves St. Laurent outfit, very simple but very expensive, with the balmy sea breezes flowing through her dark hair. The young senator’s wife clearly made an impression on Onassis. “She had a withdrawn quality,” recalled Onassis, who later claimed he detected her “carnal soul” during this brief tour. “She wasn’t conspicuously friendly, but she had a way of making you look at her.”

Jacqueline Kennedy and Senator John F. Kennedy at a 1960 campaign stop. (Photo: © Jeff Dean)
Jacqueline Kennedy and Senator John F. Kennedy at a 1960 campaign stop. (Photo: © Jeff Dean)

Senator Kennedy didn’t give much mind to Onassis. He’d met him a few times before, at social events in New York and Washington, though they’d never exchanged more than a few pleasant words. He thanked Onassis for sending a courier bearing the invitation and focused his attention on impressing Sir Winston.

By late that day, however, Churchill seemed fatigued and unable to focus. In departing, Jack Kennedy knew he’d failed to impress Churchill, barely registering a significant comment from the renowned leader he so admired. Jackie, who’d left her own mark aboard the yacht, recognized the huge missed opportunity it meant for him.

“I felt sorry for Jack that evening because he was meeting his hero, only he met him too late,” Jackie later recalled. “Think of all he could have — he was so hungry to talk with Churchill at last, or meet him, and he just met Churchill when Churchill couldn’t really say anything.”

That night, Jackie tried to make light of the situation and ease her husband’s pain. “Maybe he thought you were the waiter, Jack,” she teased.

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Winston Churchill’s eighth and final voyage aboard Onassis’s giant yacht began in June 1963, with guests that included Prince Stanislas Radziwill and his wife, Lee, Jackie Kennedy’s sister. The Radziwills presented themselves as a happily married royal couple, but in reality, Lee already had confided to friends that she wanted a divorce and was looking for a richer and better-known man. “My God, how jealous she is of Jackie. I never knew,” Lee’s confidant Truman Capote told Cecil Beaton, the famed British photographer. “Understand her marriage is all but finito.”

Later that year, there would be another journey on the Onassis yacht with Lee and her sister Jackie, by then the wife of the U.S. President. The death of their baby Patrick in August placed unbearable stress on the Kennedy marriage, compelling Jackie to stay away from Washington for the rest of summer of 1963. In September, she accepted an invitation to relax with her sister, Lee, aboard Onassis’s yacht, cruising along the Mediterranean — just as Sir Winston Churchill had enjoyed. “The ship will go wherever Mrs. Kennedy wants it to go,” Onassis insisted. “She is the captain.”

Onassis’s generosity with Jacqueline Kennedy, as with the Churchills, was more manipulative than it appeared on the surface. His invitation came with the price of access to both the First Lady and, by extension, the President of the United States. Though at times rivalrous, the two sisters depended on each other emotionally when in need. At Ari’s urging, Lee relayed his offer to make the giant yacht available to Jackie for a relaxing escape. “You can’t imagine how terrific Ari’s yacht is, and he says we can go anywhere we want,” Lee explained. “It will do you so much good to get away for a while.”

Realizing the political sensitivities involved, Onassis volunteered to stay away from the yacht while the First Lady was aboard. Jackie wouldn’t have it. In agreeing to the voyage, she insisted Onassis join them. Jackie told her sister that she “could not accept his generous hospitality and then not let him come along.” Uncharacteristically, Onassis remained below decks, to avoid the chance of being photographed with the First Lady.

Greek tycoon Aristotle Onassis in 1967. (Photo: Nationaal Archief)
Greek tycoon Aristotle Onassis in 1967. (Photo: Nationaal Archief)

In recounting her Greek getaway, Jackie Kennedy later claimed the president encouraged her to take a trip, to lift her depressed mood after their baby died. “Why don’t you go to New York, or go see your sister in Italy?” Jack told her, as she later recounted to Arthur Schlesinger. But other accounts say the president reacted strongly against the idea — “looking like thunder,” as his personal secretary, Evelyn Lincoln, recalled.

“For Christ’s sake, Jackie!” the president protested to his wife. “Onassis is an international pirate!” Of course, Onassis’s checkered past didn’t stop JFK himself from previously boarding the yacht to see Winston Churchill. However, the president wasn’t in a bargaining position to veto his wife’s invitation. “Jackie had made up her mind,” Lincoln recalled about the Onassis trip, “and that was that.”

Nevertheless, the president took steps to ensure that his wife’s recovery didn’t become a political weapon. He arranged for Franklin D. Roosevelt Jr., then undersecretary of commerce, and Roosevelt’s wife to accompany the First Lady, lending the trip an air of official business. “Your presence will add a little respectability to the whole thing,” Jack assured FDR’s son.

For the Kennedys, Lee Radziwill also posed a problem. Her second marriage, to Prince Radziwill, was falling apart by the time Jackie left for Greece. Newspaper columnists speculated about her alleged affair with Onassis. “Does the ambitious Greek tycoon hope to become the brother-in-law of the American President?” asked syndicated columnist Drew Pearson. The Kennedys feared a wider scandal with their Catholic supporters if the First Lady’s sister became embroiled in a public spectacle with Onassis. “Just tell her to cool it, will you?” Jack’s brother, Attorney General Robert Kennedy, pleaded with Jackie.

Instead, Jackie turned on her own charm during her Greek odyssey. With each passing moment on the yacht, her spirits improved and she revived, looking ever more radiant. The Christina’s luxury proved everything she’d heard, all that Lee had promised — a Shangri-La on the sea. By day, they sunned themselves and relaxed on the ship, with a staff that included two hairdressers and a Swedish masseur. At night, Ari’s waiters served vintage wines, caviar and exotic foods, while a small orchestra provided dancing music.

Well past midnight, Jackie chatted with her engaging host in French as well as English. Onassis was much different from her husband: a self-made creation, more of a rogue in the vein of Joe Kennedy. Most significant, Ari, a master of seduction, seemed totally focused on Jackie’s needs and not his own. The Greek tycoon, already linked to Maria Callas and the president’s sister-in-law, now found himself deeply attracted to the most elusive prize of all. “What was really happening on the cruise was that Aristotle Onassis was falling in love with the First Lady of the United States,” explained his biographer, Frank Brady. Though Ari stayed out of sight at first, he joined his guests when the yacht docked in Turkey, and the paparazzi took photos of the happy revellers. Eventually, a long-lens photo of Jackie in a bikini, sunning herself aboard the Christina, appeared in newspapers around the world.

Back in the United States, a Republican congressman complained about the public expense surrounding the First Lady’s luxury trip aboard a yacht owned by a foreigner who’d defrauded the government. Under a headline “First Lady’s Cruise Causes Stir,” Drew Pearson sniffed around Onassis’s shipping deals. Jack and his attorney general brother were furious. Bobby ordered Secret Service agents to place a security blackout around Jackie to avoid further publicity. J. Edgar Hoover’s FBI reviewed its files on Onassis. In a perturbed call to the yacht, the president asked his wife to return home.

Jackie decided to stay a bit longer. It was the kind of ploy (the distant trip) that other wives of famous men, including Clementine Churchill and Jackie’s mother-in-law, Rose, employed to make an implicit point with their husbands and establish some equilibrium for themselves. When she finally returned to America, the First Lady received expensive jewelry from Onassis, a diamond-and-ruby necklace — far better than Lee’s parting gift. Afterward, as if to underline the sisters’ rivalry, Lee jokingly complained to Jack that “while Jackie has been laden with presents, I only received three dinky little bracelets that Caroline wouldn’t wear to her own birthday party.”

Jackie raved about her trip, telling the president how refreshed she felt. She sent Ari a cigarette box as a gift of thanks. Gradually, the First Lady realized the political damage she’d caused. “I was melancholy after the death of our baby and I stayed away…longer than I needed to,” Jackie later confided to a family priest, Rev. Richard McSorley, a Georgetown Jesuit. “I could have made life so much happier, especially for the last few weeks. I could have tried harder to get over my melancholy.” She particularly felt bad about the barbs Franklin D. Roosevelt Jr. received from the press, who implied Onassis was trying to unduly influence his Commerce Department’s maritime interests. “Poor Franklin didn’t want to go along at all,” Jackie explained to Ben Bradlee of the Washington Post.

Bradlee and his wife had accompanied the Kennedys to view a new James Bond movie when the subject of their discussion drifted to who might succeed Jack as president someday. Assuming his brothers weren’t ready yet, Jack reeled off names of people he couldn’t support, including Vice President Lyndon Johnson.

“Well, then who?” Jackie finally asked.

“It was going to be Franklin, until you and Onassis fixed that,” Jack teased.

Bradlee recalled how the president later used “Jackie’s guilty feelings” about Onassis to convince her to accompany him on his next political trip, this time to Dallas, something she was loath to do.

“Maybe now you’ll come with us to Texas next month,” Jack said, beaming his all-American smile. His wife wouldn’t resist.

“Sure I will, Jack,” she agreed.

The 1964 presidential campaign was expected to be Jack Kennedy’s last. Unlike in England, he couldn’t become his nation’s leader again, as Winston Churchill did in 1951, six years after last leaving the prime ministership.

“It has recently been suggested that whether I serve one or two terms in the Presidency, I will find myself at the end of that period at what might be called an awkward age — too old to begin a new career, and too young to write my memoirs,” Kennedy said, alluding once more to his hero. The events in Dallas on November 22, 1963 would forever change that.

As the world mourned JFK’s assassination, Onassis called Lee Radziwill in London. Lee asked him to accompany her and her husband to the president’s funeral. A formal invitation allowed Onassis to stay at the White House, one of a small group of non-family members.

Jackie Kennedy, her children,and Robert F. Kennedy  leave the U.S. Capitol after John F. Kennedy's funeral on November 25, 1963. (Photo: Abbie Rowe White House Photographs)
Jackie Kennedy, her children,and Robert F. Kennedy  leave the U.S. Capitol after John F. Kennedy’s funeral on November 25, 1963. (Photo: Abbie Rowe White House Photographs)

A month earlier, Jack and Bobby had talked of banning the Greek shipping magnate from the United States, at least until the 1964 election. Now neither Lee nor her bereaved sister thought of keeping him away. Ari was among the few who paid his respects to the widowed First Lady in her private suite.

On Sunday, November 24, the Greek tycoon attended an informal White House dinner that resembled an Irish wake. Kennedy’s brothers, Bobby and Teddy, and many of their closest friends shared drinks and humorous stories about Jack. The party felt as if Jack had never died, that his body wasn’t lying in state in the Capitol.

Surprised by this strange Irish custom, Onassis played along as best he could. “Ari quickly discovered his role as a kind of court jester,” his biographer Peter Evans explained. “It was a part he had played often for Churchill, and he was prepared to play it again for the Kennedys.” Perhaps desperate for diversion from his grief, Bobby asked Ari about his colorful past, about his famous yacht, and wondered aloud if the stools on board were really covered with the genitalia of whales.

Later, Bobby waved around a fake document and asked Onassis to sign it. The paper bequeathed half his money to the poor in Latin America. “I have never made the mistake of thinking it is a sin to make money,” Ari said, somewhat in jest, the kind of comment Jack Kennedy’s father might have employed.

Bobby Kennedy’s excess on this night could surely be forgiven. Since learning of his brother’s death, he had found his life a whirl of agony, pain and recriminations while trying to comfort Jackie and his family. Another guest in the White House heard him crying alone in the Lincoln Bedroom, “Why God, why?” While the nation’s top investigator searched in his mind for answers to a senseless crime, Bobby attended to funeral arrangements and the personal care of Jack’s widow and family.

In 1968, Jackie decided to marry Aristotle Onassis, whom she’d met a decade earlier when her husband visited Churchill aboard the Greek magnate’s boat. Few knew of her intentions, including her mother-in-law Rose. Onassis had been the self-described “invisible man” in Jackie’s life. He visited her regularly after she moved from Washington to her Fifth Avenue apartment in Manhattan with her two children.

When Bobby learned of Jackie’s impending marriage to Onassis, he tried to dissuade her. Failing that, he urged her not to mention her plans publicly while he was running for president in 1968. Just as Bobby had managed to keep his controversial father, former Ambassador Joe Kennedy, away from the press in the 1960 race, Jacqueline Kennedy agreed to keep her relationship with Onassis out of the public’s glare.

“I know this is what the Ambassador would want me to do,” she told friends about the Onassis subterfuge. Yet she couldn’t hide her dread. “Do you know what I think will happen to Bobby?” she told historian friend Arthur M. Schlesinger Jr. “The same thing that happened to Jack. I’ve told Bobby this, but he isn’t fatalistic, like me.”

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Excerpted from the book When Lions Roar: The Churchills and the Kennedys by Thomas Maier. Copyright © 2014 by Thomas Maier. Excerpted by permission of Crown Publishing, a division of Penguin Random House. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

Andrew Standeven is a freelance illustrator and fine artist – as well as an equestrian, historical reenactor, university librarian and FedEx courier – residing in Boston, Massachusetts.