Donald Trump spent more than $250,000 from his charitable foundation to settle lawsuits that involved the businessman's for-profit businesses, according to interviews and a review of legal documents.

Those cases, which together used $258,000 from Trump's charity, were among four newly documented expenditures in which Trump may have violated laws against "self-dealing" -- which prohibit nonprofit leaders from using charity money to benefit themselves or their businesses.

In one case, from 2007, Trump's Mar-a-Lago Club faced $120,000 in unpaid fines from the city of Palm Beach, Fla., resulting from a dispute over the size of a flagpole.

In a settlement, Palm Beach agreed to waive those fines if Trump's club made a $100,000 donation to a specific charity for veterans. Instead, Trump sent a check from the Donald J. Trump Foundation, a charity funded almost entirely by other people's money, according to tax records.

In another case, court papers say one of Trump's golf courses in New York agreed to settle a lawsuit by making a donation to the plaintiff's chosen charity. A $158,000 donation was made by the Trump Foundation, according to tax records.

The other expenditures involved smaller amounts. In 2013, Trump used $5,000 from the foundation to buy advertisements touting his chain of hotels in programs for three events organized by a D.C. preservation group.

If the Internal Revenue Service were to find that Trump violated self-dealing rules, the agency could require him to pay penalty taxes or to reimburse the foundation for all the money it spent on his behalf. Trump is also facing scrutiny from the office of the New York attorney general, which is examining whether the foundation broke state charity laws.

The Trump campaign did not respond with answers to a detailed list of questions about the cases.

The New York attorney general's office declined to comment when asked whether its inquiry would cover these new cases of possible self-dealing.

Trump founded his charity in 1987 and for years was its only donor. But in 2006, Trump gave away almost all of the money he had donated to the foundation, leaving it with just $4,238 at year's end, according to tax records.

Trump gave relatively small donations in 2007 and 2008, and afterward nothing. The foundation's tax records show no donations from Trump since 2009.

Its money has come from other donors, most notably pro-wrestling executives Vince and Linda McMahon, who gave a total of $5 million from 2007-09, tax records show. Trump remains the foundation's president, and he told the IRS in his latest public filings that he works half an hour per week on the charity.

The new cases of possible self-dealing were discovered in the Trump Foundation's tax filings. While Trump has refused to release his personal tax returns, the foundation's filings are required to be public.

The case involving the flagpole at Trump's oceanfront Mar-a-Lago Club began in 2006, when the club put up a giant American flag on the 80-foot pole. Town rules said flagpoles should be 42 feet high at most. Trump's contention, according to news reports, was: "You don't need a permit to put up the American flag."

The town began to fine Trump $1,250 per day. Trump's club sued in federal court, saying that a smaller flagpole "would fail to appropriately express the magnitude of Donald J. Trump's ... patriotism."

They settled. The town waived the $120,000 in fines. In September 2007, Trump wrote the town a letter, saying he had done his part as well.

"I have sent a check for $100,000 to Fisher House," he wrote.

The town had chosen Fisher House, which runs a network of comfort homes for the families of veterans and military personnel receiving medical treatment, as the recipient of the money. Trump added that, for good measure, "I have sent a check for $25,000" to another charity, the American Veterans Disabled for Life Memorial.

Trump provided the town with copies of the checks, which show that they were from the Trump Foundation.

A Section on 09/21/2016