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Where JFK once thrilled Palm Beach would President Trump do the same?

By Brian E. Crowley

On the 1960 British Pathé newsreel, the headline says "Kennedy talks strategy with Congress leaders." Palm Beach was used to its Kennedys but not like this. For the first time, this quiet island whose residents valued privacy as much as wealth, was becoming the center of world attention.

In one of his first post-election meetings, John F. Kennedy summoned his newly elected vice president, Lyndon Johnson, and congressional leaders to discuss his plans after his inauguration. It would be the first of many visits to the Kennedy home on the island of 6,000 residents by national and world leaders. The north end island Kennedy home was now the Winter White House. 

Now, more than a half century later, Palm Beach is again a political spectacle. Only this time, the Winter White House could be Donald Trump’s Mar-a-Lago. If JFK was of the Mad Men generation, Trump is a Twitter-boomer. If JFK brought youthful vigor to the island and willingness to blend, Trump stormed the island, determined to bend it to his will.

JFK brought glamour. Trump brought New York attitude and new money glitz. And while old Palm Beach may cringe, Trump is there to stay whether he wins or not.

The Kennedys arrived in Palm Beach when family patriarch Joseph Kennedy bought a home there in 1933. There were 1,700 residents. The island, like much of Florida, was segregated. But it was much more than a division of whites and blacks. It was a division of Jews and Gentiles, the extraordinarily wealthy and the lower classes.

Joe was a member of the then notoriously segregated Everglades Club which excluded minorities, Jews, and anyone who simply didn’t measure up to their elite standard.

By the time his second son was elected president, Palm Beach’s population had climbed to more than 6,000. The island remained deeply segregated and attitudes had changed little from when Joe Kennedy first bought a home there 27 years earlier.

JFK made frequent trips to Palm Beach during his presidency. One Kennedy home video, shows Kennedy playing in the family pool with his very young children Caroline and John Jr. JFK is seen tossing a ball to a pair of dogs running beside the pool.



Palm Beachers still like to see old black-and-white pictures of the First Couple going to St. Edwards Catholic Church, JFK holding press conferences, and the children at play.

Five years before Donald Trump arrived in Palm Beach, attorney Allen DeWeese had been arrested by Palm Beach Police for jogging shirtless. The town council had passed an ordinance declaring jogging shirtless to be indecent exposure. Violators faced up to 60 days in jail or a $500 fine.

In court, the town argued that it had a right “to protect the beholder of unsightly displays.”  A judge tossed out the arrest calling the ordinance not only unconstitutional but “silly.”

Palm Beach may have lost the case but not its belief that every aspect of living on the island must be regulated. From the height of a resident’s hedges to the types of companies allowed to do business there, the town is ever alert for the smallest infraction.

New businesses are suspect. They must prove that most of their customers will be people who live there. Some fought the opening of a Starbucks fearing that it would attract outsiders.

When Trump arrived in 1985, islanders soon found out he would have little regard for the town’s many rules and regulations.

That year, Trump purchased the aging and neglected Mar-a-Lago. It had been the home of cereal heiress Marjorie Merriweather Post, a spectacular 1927 mansion with 58 bedrooms and 33 bathrooms. When she died in 1973, Post willed Mar-a-Lago to the U.S. government dreaming that it would become a presidential retreat. But the government said it couldn’t afford the upkeep and declined the gift.

Mar-a-Lago sat empty, haunting the sensibilities of the town until Trump swooped in and bought it for $10 million. It would be the start of a series of lawsuits and threatened lawsuits as Trump demanded zoning and other concessions from the town.

Trump won repeatedly until he was eventually able to turn Mar-a-Lago into an exclusive club with membership costing $100,000. One of his most outrageous moments in the view of the town was when Trump decided to fly a used-car-lot size American Flag on a 90 foot pole on Mar-a-Lago’s lawn.

The town said take it down. Trump sued. The Town backed down in exchange for a slightly smaller flag and pole.

Now, the town, which is about 2-1 Republican and home to conservative stars Rush Limbaugh and Ann Coulter, faces the possibility that the flag will be flying over another Winter White House – Mar-a-Lago.


(This story first appeared in Florida Weekly)



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