For the next decade, Mr. Trump and the town argued over such issues as the best way to fireproof Mar-a-Lago’s 16th-century Portuguese tapestries, unauthorized photo shoots and Mr. Trump’s plans to build a marina. (That would have required dredging nearby Lake Worth, which is tightly regulated by local, state and federal officials.)
In 2000, town leaders threatened penalties against Mr. Trump’s club over a brunch invitation — they said it suggested the club was being used for an event by an outside business. Then, in 2006, officials cited Mr. Trump for a string of other violations at Mar-a-Lago, including the height of his ficus hedges (too low) and attendance at an Elton John concert (too high).
Aggrieved, Mr. Trump protested the concert complaint. “I am deeply disappointed that the town would want to penalize my efforts to host one of the world’s foremost entertainers for a very worthwhile charity and an evening which brought great acclaim to Palm Beach,” he wrote in a letter. “It is unfortunate that the town continues to take such a harsh tone when it comes to the Mar-a-Lago Club and Donald Trump.”
Four months after he sent the letter, he went on the offensive using an unconventional weapon: an 80-foot flagpole in front of the club. His lawyers argued that only a pole of that size could adequately convey Mr. Trump’s patriotism. Officials fined him, and he sued, accusing them of violating his right to free speech, before reaching a settlement.
In another lawsuit, filed against the City of Doral, Fla., shortly before Mr. Trump announced his candidacy, his lawyers argued that a ban on using lawn mowers before 7:30 a.m. infringed on his right to due process. Mr. Trump dropped the suit days later and opted to negotiate with the city.
Melissa Nathan, a spokeswoman for the Trump Organization, declined to answer questions or…