In 2007, Donald Trump spent $20,000 that belonged to his charity — the Donald J. Trump Foundation — to buy a six-foot-tall portrait of himself during a fundraiser auction at his Mar-a-Lago Club in Florida.
That purchase was reported Sunday by The Washington Post. Since then, the portrait has been the center of a mystery: What did Trump do with the painting after he bought it?
If Trump did not give the painting to a charity — or find a way to use it for charitable purposes — he may have violated IRS rules against “self-dealing,” which prohibit nonprofit leaders from spending charity money on themselves.
On Wednesday, a new clue emerged. A former production manager for the portrait’s painter told The Post that he had shipped the painting — at the request of Trump’s wife, Melania — to Trump National Golf Club Westchester in Briarcliff Manor, N.Y.
Jody Young, the painter’s former manager, said that at the time he had spoken directly to Melania Trump about how the painting would be framed and displayed.
Her plan was “to hang it in either the boardroom or the conference room of the club,” Young said.
It is still unclear where the painting is now, or how long — if any time at all — it was on display at the private golf club. But tax experts say that an arrangement like the one described by Young could violate Internal Revenue Service rules.
If the painting is still hanging in the club, “it’s on display, in his business enterprise. It’s not on display in a charitable enterprise. It is arguably enhancing the experience of playing golf there,” said Marc Owens, the former director of the IRS division overseeing tax-exempt enterprises. “It’s not a charitable use. It is a noncharitable use.”
The Post sent questions about the portrait to the Trump campaign Wednesday afternoon via email, text and voice-mail message. The Trump campaign did not respond. The Post also tried to view the portrait at Trump National but was turned away at the club’s entrance.
On Tuesday, President Obama cited the painting as he campaigned for Democratic nominee Hillary Clinton — using it to contrast Trump’s foundation with the much larger Clinton Foundation.
“You want to debate foundations and charities?” Obama said. “One candidate’s family foundation has saved countless lives around the world. The other candidate’s foundation took money other people gave to his charity and then bought a six-foot-tall painting of himself.”
The Post was also shown a picture of the painting for the first time on Wednesday. The photo was taken during the auction and does not show where the portrait might be now.
Michael Israel, the artist who made the painting, declined to comment Wednesday. In an earlier interview, he said of the painting: “I understand it went to one of his golf courses.” At that time, Israel was not sure which course the painting had gone to.
The portrait was made at a benefit for a Florida charity, the Children’s Place at Home Safe at Mar-a-Lago in November 2007.
Both Donald and Melania Trump attended, sitting near the stage, according to photos viewed by The Post. The entertainment was Israel, who bills himself as “the original speed painter.”
Young said that Israel had been notified ahead of time that Trump would be there — and had planned to paint a portrait of him during his frenetic show.
During a typical Israel performance, he paints five or six paintings in just 30 minutes. Music plays. Paint splatters Young, who handled the logistics. He had formerly worked for the fruit-smashing comedian Gallagher.
“I had experience with plastic,” he said. “Splattering watermelon and splattering paint — it’s kind of the same effect.”
That night, according to the picture The Post viewed, Israel painted Trump in a white dress shirt and blue tie, with broad strokes to show his trademark mane of hair. Israel also painted portraits of golfer Paula Creamer, John Lennon and a firefighter carrying a young girl.
Afterward, the paintings were auctioned by David Schall, an auctioneer who traveled with Israel. He stood on the stage in wet paint. He sold the Trump painting last.
At first, Schall said, there were two bidders: Melania Trump and Creamer. Then Creamer bowed out, saying the price had gone too high.
Then it was only Melania Trump, bidding $10,000.
Schall pushed her to go higher.
“I don’t think anyone’s going to bid against you, and perhaps you should consider doubling your bid,” Schall, during a telephone interview Wednesday, recalled saying. “And I think she might have turned to Donald Trump, and I guess she got the go-ahead.”
“And there we were at 20,000,” Schall recalled. “Big round of applause, and everybody was excited.”
The painting sold.
“It really wasn’t a lot,” Schall said. Schall said he had sold paintings for much more: Paintings of the Beatles had gone for more than $30,000. Young recalled another painting, of billionaire Warren Buffett, which sold for more than $100,000.
During the auction that night, Schall had worked the room, and he remembers good-naturedly ribbing Melania Trump from the stage. “‘I think everybody wants to know, Mrs. Trump, if this is going to end up in the boardroom or the bedroom.’ Lots of laughter. She didn’t say anything.”
The answer, apparently, was the boardroom.
Young said that after the show, he took the painting back to a warehouse, let the acrylic paint dry, then rolled it up for shipping.
He said Melania Trump directed him on where to send it.
“She asked that it be shipped to the Westchester golf club, I recall, and we had several phone conversations involved in re-framing the canvas,” Young said.
Later, a check was sent to The Children’s Place at Home Safe. The check came from the Donald J. Trump Foundation. Melania Trump is not an officer of that charity, but her husband is its president.
An executive from the children’s charity, now called HomeSafe, said the charity had split the money with the artist.
Later, when the Trump Foundation completed its tax filings for 2007, there was a line on the IRS form that asked if it had violated rules by using charity money to “furnish goods, services, or facilities” to one of its officers.
The Trump Foundation checked “no.”
Donald Trump signed the form.
If the IRS determined that the purchase of the painting was a prohibited act of “self-dealing” by Trump, it could impose penalties on both the foundation and on him.
Owens, the former IRS official, said the agency could also impose tax penalties for filing an incorrect return.
“The question is: Did the person who signed the return — was that a knowingly false answer to that question?” said Owens, now a partner with the firm Loeb & Loeb. He said that Trump might be able to defend himself by saying that he was not aware the answer to the self-dealing question was wrong.
On the night of the auction, it appeared that Melania Trump had some reservations about the painting she’d just purchased.
She approached the artist and pointed out a few details she believed he had not captured accurately.
“[It’s] very rare that anybody has any commentary. They’re usually so blown away they don’t have anything to say about the artwork,” Israel told The Post. “It wasn’t like a critique. It was just, ‘I think this would be like this, and I realize that you did this very fast.’ ”
Alice Crites and Philip Bump contributed to this report.