The Secret History of a Kennedy Encounter

How a secret Mediterranean meeting between JFK, Winston Churchill and a billionaire shipping magnate led to a wrinkle in the future president’s marriage—and laid the seeds of what would blossom into Jackie’s second.

Illustration by Andrew Standeven

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 decid…