The Trump Files: How Donald Drove Palm Beach Nuts With an American Flag

“I guess I consider it a badge of courage.”

Ivylise Simones


Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of GOP nominee Donald Trump.

We all know Donald Trump firmly believes that size matters. It turns out it matters just as much to him when it comes to the American flag.

Trump waged a yearslong battle with the blue bloods of Palm Beach, Florida, the city where his Mar-a-Lago club is located, over everything from his parties to his plans to convert the former mansion to a club and noise from the local airport. Trump launched yet another fight in 2006 when he put up an American flag that smashed the city’s flag-flying rules. Palm Beach ordinances allowed for flags up to 4 feet by 6 feet on poles as high as 42 feet; Trump’s flag, according to the Sun-Sentinel, was a gargantuan 25 feet by 50 feet on a flagpole 80 feet high.

The city started fining Trump $1,250 a day for flying the flag, but the tycoon was gleeful. “This is a dream to have someone sue me to take down the American flag,” he told CNN’s Nancy Grace in January 2007. The city did not in fact sue, but Trump—predictably—did. He filed a $25 million federal suit against Palm Beach, alleging that the city had violated his free speech and equal protection rights in going after his flag. Flying a smaller flag, the suit claimed, “would fail to appropriately express the magnitude of Donald J. Trump’s…patriotism.” Trump also pledged to donate any damages to veterans returning from the war in Iraq.

After what the Sun-Sentinel said were “secret, court-ordered negotiations,” Trump and the city struck a deal in April 2007. The city would drop the $120,000 in fines against Trump and allow him to keep the flag on a slightly shorter but still technically illegal 70-foot flagpole. Trump, for his part, would drop the suit and donate $100,000 to a veterans’ charity.

According to the Washington Post, Trump wrote to the city a few months later to brag that he’d sent $100,000 to Fisher House, a charity that helps house families visiting hospitalized veterans, and thrown in $25,000 for the American Veterans Disabled for Life Memorial out of the goodness of his heart. But there was still one Trumpian twist to the story. He made the contributions through his foundation—a move that was possibly illegal—which was primarily funded by other people’s money.

Read the rest of “The Trump Files”:

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