Donald Trump spent more than a quarter-million dollars from his charitable foundation to settle lawsuits that involved the billionaire’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 town 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.

The check to charity from the Trump Foundation.

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. And in 2014, Trump spent $10,000 of the foundation’s money for a portrait of himself bought at a charity fundraiser.

Or, rather, another portrait of himself.

Several years earlier, Trump had used $20,000 from the Trump Foundation to buy a different, six foot-tall portrait.

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.

More broadly, these cases also provide new evidence that Trump ran his charity in a way that may have violated U.S. tax law and gone against the moral conventions of philanthropy.

“I represent 700 nonprofits a year, and I’ve never encountered anything so brazen,” said Jeffrey Tenenbaum, who advises charities at the Venable law firm in Washington. After The Post described the details of these Trump Foundation gifts, Tenenbaum described them as “really shocking.”

“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 a while,” Tenenbaum said.

The Post sent the Trump campaign a detailed list of questions about the four cases, but received no response.