Donald Trump the Philanthropist Is Known for His Reluctance

More Trump illusions.

When Donald J. Trump made an appearance this spring at the New York Military Academy, his high school alma mater in Cornwall-on-Hudson, he spoke of it with gratitude and in glowing terms, describing it as “one of the really great military academies.”

“I had such incredible experiences here,” Mr. Trump told a crowd during a campaign stop in April.

But six years ago, when it was on the verge of closing under the weight of debt, and a small group from the school came to Trump Tower seeking financial assistance, Mr. Trump gave a swift and firm response: No.

“We were disappointed,” said Rich Pezzullo, an alumnus who attended the meeting, which took place as Mr. Trump was participating in an online real estate auction and ended when the winner of his Miss USA pageant showed up. “We thought he’d open up his checkbook,” Mr. Pezzullo said.

Over the years, Mr. Trump has billed himself as an “ardent philanthropist,” and his official biography says that he is “involved with numerous civic and charitable organizations.”

But the depiction of Mr. Trump as a generous benefactor has recently come into question amid a series of reports raising doubts about whether he has followed through on his lavish pledges, whether he misused the foundation that bears his name and whether he financially supports it at all.

Interviews with people who have worked with or solicited money from him, as well as years of publicly available charity records, paint a picture of Mr. Trump as a reluctant giver despite his wealth. Donations from his foundation, which in recent years has been exclusively financed by others, sometimes served his own needs while helping the recipients.

Jack O’Donnell, who was president and chief operating officer of Trump Plaza Hotel & Casino in the late 1980s, said Mr. Trump would question the need for donations, even those as small as a couple thousand dollars.

“He’d say ‘Why are we doing this?’ or ‘Do we have to give this much?’ ” said Mr. O’Donnell, who parted ways with Mr. Trump on bad terms and was described by the Trump campaign as a disgruntled former employee. “I don’t know how else to put it: He’s cheap.”

Mr. Trump’s philanthropic endeavors over the past four decades have been dotted with pledges to donate the proceeds from books or speeches. Sometimes, Mr. Trump has stepped in to help a person in need, with the cameras rolling. And Mr. Trump, usually accompanied by his wife, Melania, has been a familiar face at well-publicized benefit galas in New York and Florida, where the rich and famous mingle and are seen.

He has also more quietly supported other causes over the years. He has donated to and sits on the board of the Police Athletic League, a youth sports organization in New York. And Mr. Trump has won a lifetime achievement award from the American Cancer Society for his giving.

“At the end of the day, in my narrow world, he’s a board member who has consistently contributed to us,” said Frederick Watts, the executive director of the Police Athletic League.

Mr. Trump’s campaign, in response to questions about his giving practices, called him “extremely generous with both his time and his money.”

“Mr. Trump regularly makes personal contributions to worthy charitable causes and organizations, but does not seek recognition,” his spokeswoman, Hope Hicks, said in an email. “Mr. Trump has made several significant contributions to the Trump Foundation, including an initial multimillion-dollar lump sum at its inception. Since then he has made personal contributions, and regularly waives fees for appearances, speeches and publicity rights instead encouraging the donations be made to charity.”

In 1987 Mr. Trump started the Donald J. Trump Foundation, a nonprofit through which his own donations and those of others are channeled to causes and institutions. Through 2014, according to the foundation’s tax filings, he had donated $5.4 million to the foundation, a small fraction of his self-described net worth of billions of dollars.

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