Some of the settlements center around issues with Trump’s New York golf course and his Mar-a-Lago Club in Florida, tax records and legal documents reveal. The Republican presidential candidate’s Florida resort accrued some $120,000 in unpaid fines from the city of Palm Beach in 2007 concerning an issue over the size of a pole used to hoist the American flag.
The legal maximum is 42 feet, and a pole on Trump’s property was 80 feet tall. Trump said, at the time, "You don’t need a permit to put up the American flag." A representative at the club claimed in federal court that a shorter flagpole "would fail to appropriately express the magnitude of Donald J. Trump’s patriotism."
The city agreed to waive the fines on the condition that the real estate magnate donate $100,000 to a charity for veterans. A check was received, written on an account belonging to the Donald J. Trump Foundation, an organization funded almost exclusively through donations. The settlement terms for the golf course included Trump donating $158,000 to a charity of the plaintiff’s choice. Those funds also came from the Trump Foundation charity.
Smaller amounts include $10,000 from the Trump Foundation charity spent on a portrait of the candidate in 2014, and $5,000 spent in 2013 on advertising for the reality television star’s hotel chain, again paid for by the charity.
Trump would likely not face jail time if found guilty of self-dealing, but the Internal Revenue Service (IRS) could compel him to reimburse the foundation and pay penalty taxes. Lawyer Jeffrey S. Tennenbaum called the handling of Trump charity money "really shocking" and told the Washington Post, "I represent 700 nonprofits a year, and I’ve never encountered anything so brazen," adding, "If he’s using other people’s money, run through his foundation, to satisfy his personal obligations, then that’s about as blatant an example of self-dealing [as] I’ve seen in awhile."
Trump has described himself as an "ardent philanthropist" and has claimed to have donated $100 million dollars to charity, with little documentation. In an August email to the Associated Press he claimed, "I give to hundreds of charities and people in need of help. It is one of the things I most like doing and one of the great reasons to have made a lot of money."
Trump has shrugged off calls to release his tax returns, which would answer many questions about his financial dealings. In late August, a poll by Quinnipiac University indicated that 74 percent of participating voters want Trump to release his tax returns, including 64 percent of Republicans.