The Kennedys and Palm Beach: A Story Woven Into the Canvas

A reflection after reading “On his 108th birthday, remembering John F. Kennedy's time in Palm Beach”, by Kristina Webb in May 29, 2025’s Palm Beach Daily News

As a portrait artist, I have always been drawn to cultural figures who not only shaped history, but inhabited it. People whose presence is still felt decades later, in the cities and spaces they once called home; where they vacationed, dined, or perhaps socialized.

Few names carry as much weight in American history and Palm Beach lore as The Kennedys.

Reading the Shiny Sheet this week (or The Palm Beach Daily News if you’re formal) there was a fantastic story by Kristina Webb on JFK’s deep roots in Palm Beach, which anchored for me why I’ve painted the Kennedys as many times as I have, especially Jackie. She wasn’t just a First Lady, he was a symbol of grace, power, and restraint. In my series of Jackie portraits, I have placed her in iconic Palm Beach settings - The Colony, The Breakers, and even standing at the Worth Avenue clock tower, looking into the future. Through her sunglasses, we see the world as she might have seen it: elegant, thoughtful, and steeped in story.

It is no coincidence that Jackie and John F. Kennedy both spent so much time here. Palm Beach wasn’t just a retreat, it was their Winter White House, a canvas for presidential moments, and a refuge for a family that redefined American politics and culture.

JFK wrote his famous book, Profiles in Courage, here at age 38. He walked Worth Avenue in khakis and loafers. He sat in church pews at St. Edward’s and sipped milkshakes at Green’s Pharmacy. His transition into the White House happened on these streets, and his final weekend alive was spent here in Palm Beach with his father, just before Dallas. That kind of full-circle connection is rare.

My painting titled “Nov. 22, 1963” JFK honors that gravity. It’s part of a broader series I created on American presidents who were assassinated and it was an effort to hold space for the emotional undercurrents of history that often get flattened by headlines.

But, it is Jackie who continues to inspire me most. In Jackie at the Colony, I explored how three versions of her in Palm Beach - past and present - could live in her mirrored lenses. In Jackie at JFK’s Inauguration, her sunglasses are the shape of a 1960s CRT television screen, referencing how the public viewed that historic day. Her poise, her private strength, and her enduring style give artists like me something to respond to again and again.

Palm Beach may be filled with new construction and new faces, but the Kennedy legacy remains one of its most powerful brushstrokes. Their story lives not just in the architecture or headlines, but in how we remember them, and how we keep them alive through image, color, and reflection.

This is why I paint icons – not just to capture what they looked like, but to capture what they meant, especially to places like Palm Beach.

— Kyle