Supermodel Cindy Crawford and publisher-lawyer John F. Kennedy Jr. were two of the most recognizable faces of the 1990s, one dominating global fashion runways, the other redefining political media. When their worlds collided in 1995 for the launch of his ambitious magazine venture, it created a pop-culture moment that still resonates today.

More than three decades later, that collaboration is once again drawing attention. A nostalgic revival of interest in John F. Kennedy Jr.’s life with Love Story has prompted Cindy Crawford to revisit a meaningful artifact from their professional partnership, offering fans a rare, intimate glimpse behind one of the decade’s most iconic magazine covers.

Cindy Crawford recently shared a handwritten note from Kennedy dating back to their work on the debut issue of George in 1995. The note, addressed to legendary photographer Herb Ritts, reveals Kennedy’s thoughtful approach to balancing cover lines with imagery. In it, he wrote:

“Here’s the cover. It reflects hours of debating over what words and how many words to obscure your beautiful image. We hope you liked it. Talk soon, John K.”

The Instagram carousel posted on February 26, 2026, included the handwritten message alongside throwback launch photos and clips of Kennedy discussing the cover concept. The post was sparked by renewed public fascination surrounding his life, partly fueled by Love Story, especially after episode 5, titled Battery Park, aired, which dealt with the launch of the magazine. 

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As JFK Jr.'s life finds a center stage again after all these years, why is this 1995 magazine still iconic, even today?

The debut cover of George was intentionally bold. Crawford appeared dressed as George Washington, powdered wig and colonial styling, symbolizing the magazine’s mission to merge politics with mainstream celebrity culture. Kennedy described the publication as focusing on the “intersection of politics and popular culture,” an idea that felt revolutionary at the time.

During an appearance on Larry King Live, Kennedy explained why Crawford was the perfect choice. He referred to her as “sort of the symbol of American commercialism,” while also recognizing her sharp business instincts. The cover sparked headlines, especially amid rumors of a brief 1995 romance between the two following Crawford’s split from Richard Gere. She would later marry entrepreneur Rande Gerber in 1998.

Beyond speculation, however, the cover represented a turning point in media culture, one that previewed how politics and celebrity branding would increasingly intertwine in the decades ahead.

Cindy Crawford’s decision to share Kennedy’s handwritten note adds a personal layer to a collaboration that once made headlines worldwide. What began as a bold editorial experiment has now become a nostalgic reminder of a moment when fashion, fame, and political ambition intersected on a single glossy page.

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What do you think about the JFK's note that Cindy Crawford shared on her Instagram? Let us know in the comments!