Afterward, Israel auctioned the portrait off. Trump's wife Melania won the auction, with a bid of $10,000. Then the auctioneer convinced her to double it. Half of the proceeds went to Israel, the painter, and half went to the charity that hosted the event, then called the Children's Place at Home Safe. The charity is now called HomeSafe. It helps children and families harmed by domestic violence.
When a check came, however, it wasn't Trump or his wife who actually paid for the painting. Instead, it was Trump's charity -- which, even by that time, was largely filled with money from other donors, and not from Trump himself.
Tax experts say that if Trump hung the painting at one of his homes or businesses, he may have violated laws against "self-dealing." Those laws prohibit charity leaders from using money from their nonprofits to buy things for themselves, or for their businesses.
In recent weeks, The Washington Post has reported other instances in which Trump may have violated those rules. He used $258,000 from the foundation to pay off legal settlements that involved his for-profit businesses. He spent $12,000 from the charity's coffers to buy a football helmet signed by then-Denver Broncos quarterback Tim Tebow.
And he spent $10,000 to buy another portrait of himself in 2014. In that case, Trump paid $10,000 for the portrait. It was later found hanging on the wall of a sports bar at Trump's Doral golf resort. A spokesman for Trump, Boris Epshteyn, said later that Trump's business was actually just "storing" the portrait, on the charity's behalf. Tax experts said that does not cut it.
Even sight unseen, the $20,000 portrait has been seized on by Democrats as evidence that Trump was misusing his charity's money.
In September, shortly after The Post first described the $20,000 portrait, President Obama mocked the purchase during a campaign stop.
“You want to debate foundations and charities?” Obama said, comparing the Trump Foundation to the Clinton Foundation, associated with Democrat Hillary Clinton and her family. “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.”
Clinton herself used a similar line of attack in the third and final presidential debate.
"I'd be happy to compare what we do with the Trump Foundation, which took money from other people and bought a six-foot portrait of Donald," Clinton said. "I mean, who does that? It just was astonishing."
The photos that Israel provided Tuesday were taken at the 2007 event itself. They do not reveal where the portrait is now. Trump's campaign spokesmen have declined to answer questions about its current whereabouts, or whether Trump found a charitable use for it.
But in September, a former assistant to Israel provided a clue. Jody Young, the painter’s former manager, said that after the auction, he was told by Melania Trump to ship the painting to Trump's golf club in Westchester County, N.Y.
Her plan was “to hang it in either the boardroom or the conference room of the club,” Young said.