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.

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

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