But after a lawsuit, he ended up with a shorter flag pole but still higher than the town originally allowed.
On another occasion, he wanted to build mini-mansions on his property.
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He sued them again and again," said best-selling author Laurence Leamer, who has studied Trump for some of his books chronicling life in Palm Beach.
"He fights over everything, no battle is too small for him," he said. It was almost twice as tall as the town's regulations permitted.
When the town council said no, he sued and settled by getting approval to build a private club and sell memberships.
"He was very gracious and welcoming, and what struck me was the splendor of Mar-a-Lago; everything was so pristine, everything was top of the line," is the way Robin Bernstein remembers the impression she had of Trump and the club.