In the summer of 1995, John F. Kennedy Jr., the charismatic scion of America’s most storied political dynasty, found himself in an unexpected role: pitchman. The 37-year-old editor-in-chief of George, his new political lifestyle magazine, had a bold idea. He wanted to feature the world’s most famous woman—Princess Diana—as the publication’s cover star. But the meeting at the Carlyle Hotel in New York City, as detailed in Caroline Hallemann’s book The Kennedys and the Windsors, was far from a romantic encounter. Instead, it became a test of Kennedy’s charm and Diana’s sharp wit.
A Magazine Makeover for a Royal
Kennedy’s vision for George was ambitious: a blend of politics, culture, and celebrity. To launch the magazine, he needed a high-profile figure to anchor its credibility. Diana, with her global appeal and humanitarian work, seemed an ideal choice. According to Hallemann, Kennedy proposed the idea during a private meeting, armed with creative concepts for the cover shoot. “John had brought along with him several ideas for the cover shoot,” Hallemann writes, per the Daily Mail. “One featured her wearing a three-corner hat like one from the Revolutionary War, another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers.”
The imagery Kennedy suggested was as eclectic as it was symbolic. The Revolutionary War hat, a nod to American history, and the limousine scene, echoing the chaos of pap
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