2006, Trump and Palm Beach officials battled over the installation of a giant American flag on the property. As Politico reported in detail, the town fined Trump $250 a day for as long as the flag stood, saying it violated ordinances. Trump took the battle to Nancy Grace’s TV show before using his favorite weapon ― the lawsuit. He sued the city for $25 million.

Trump eventually dropped the case after the city agreed to drop its fines. He was allowed to have a slightly downsized flag and said he would donate $100,000 to veterans charities.

These kinds of squabbles weren’t an aberration. In Doral, a city of 50,000, trouble started when Trump bought a golf course in 2012. He whined about the condition of utility poles around the propertyand complained on Twitter: “In my opinion, one of the worst utility companies in the country is Florida Power and Light.”

In my opinion, one of the worst utility companies in the country is Florida Power and Light. — Donald J. Trump (@realDonaldTrump) October 8, 2013

Trump also went to war with homeowners who lived around the course. He thought their $500,000 homes were enough of a blight that in the process of renovations, he planted a dense wall of palm trees around the course. “What happens is when you are on, as an example, the first green on the golf course, you are staring at houses with laundry hanging out their window in some cases, he said at the time. “It’s not appropriate for the finest resort in the