The legendary Palm Beach history of the Kennedy dynasty was anything but politics as usual.

By Bob Davidoff/Davidoff Studios

The lavish beachfront home at 1095 N. Ocean Blvd., built by Addison Mizner in 1923 for department-store tycoon Rod-man Wanamaker, originally bore the name “La Guerida,” Spanish for “bounty of war.” For a good portion of the 20th century, the occupants of this 100-foot-long estate brought their own brand of war to Palm Beach.

The Kennedy family called 1095 N. Ocean Blvd. (currently owned by financier John Castle and wife Marianne) their high-season home for six decades; during the years when Secret Service guarded the fortified enclave, it would be known as the “Winter White House.” It marked an era when the world’s first family regularly visited Palm Beach, attending church, enjoying the beach, shopping and dining.

But there was a darker side to the Kennedy history, one that would shadow the family for decades, especially here in South Florida. The Kennedys would battle their share of personal demons and indulge in their share of vices at the North Ocean Boulevard property and other spots in Palm Beach—secrets and lies, tragedies and controversies, and historic dramas that riveted a nation.

A little more than 50 years after Jack Kennedy’s death, Boca Raton revisits what was once America’s most famous dynasty—the Kennedys—and their storied connection to Palm Beach.

Bound for Gloria

In the early 1930s, much of America was in a state of abject depression: millions lost their jobs after the stock market crash, and they couldn’t even drink their problems away, at least not legally. The same could not be said about Joseph P. Kennedy—father of John, Robert and Ted, among other privileged off-spring—who had plenty of cash and booze.

As a distributor of forbidden libations, Kennedy had earned the nickname “Bootlegger Joe”; thanks to Prohibition, he became a millionaire in his early 30s. In 1933, at age 45, he purchased La Guerida from Rodman Wanamaker for $115,000, about a third of its pre-crash market value.

According to Murray Weiss and Bill Hoffman’s Palm Beach Babylon, a compendium of area scandals, the town of Palm Beach had been in Joe Kennedy’s heart long before one of its most luxurious properties came into his possession. “Some of Joe’s most pleasant memories were of playing with his two infant sons on the beach outside the Breakers Hotel,” write the authors. 

To continue reading, please pick up a copy of
the February Boca Raton magazine.