Donald Trump's charitable foundation has received approximately $2.3 million from companies that owed money to Trump or one of his businesses but were instructed to pay Trump's tax-exempt foundation instead, according to people familiar with the transactions.
In cases where he diverted his own income to his foundation, tax experts said, Trump would still likely be required to pay taxes on the income. Trump has refused to release his personal tax returns. His campaign said he paid income tax on one of the donations, but did not respond to questions about the others.
That gift was a $400,000 payment from Comedy Central, which owed Trump an appearance fee for his 2011 "roast."
Then there were payments totaling nearly $1.9 million from a man in New York City who sells sought-after tickets and one-of-a-kind experiences to wealthy clients.
That man, Richard Ebers, bought goods and services - including tickets - from Trump or his businesses, according to two people familiar with the transactions, who requested anonymity because they were not authorized to speak about the payments. They said that Ebers was instructed to pay the Donald J. Trump Foundation instead. Ebers did not respond to requests for comment.
The gifts begin to answer one of the mysteries surrounding the foundation: Why would other people continue giving to Trump's charity when Trump himself gave his last recorded donation in 2008?
The donations from Ebers and Comedy Central, which account for half the money given to the Trump Foundation since 2008, also provide new evidence of the Trump Foundation's ties to Trump's business empire.
Did Trump, in fact, pay income tax in the cases where he directed his own fees to the Trump Foundation?
The first time The Washington Post asked, Trump's campaign denied that any of the transactions had taken place.
"He's never directed fees to the foundation," said Boris Epshteyn, a senior adviser to Trump, who responded on the campaign's behalf in a phone interview on Saturday. Epshteyn said that what Trump did was provide a service, renounce any fees, and then merely suggest that the other party make a donation to a charity of their choosing.
"He's waived fees from time to time," Epshteyn said. "He's never directed it to a specific charity."
The Post later presented Epshteyn with the Comedy Central and Ebers examples during the same interview. Epshteyn acknowledged the Comedy Central case had occurred but refused to comment on the others.
"To my knowledge, Mr. Trump has followed all applicable rules and regulations," Epshteyn wrote in an email Sunday after being presented with The Post's reporting on the donations from Ebers. "The rest is pure speculation and worthless conjecture on your part."
Previously, The Post reported that the Trump Foundation appears to have violated laws against "self-dealing," which prohibit nonprofit leaders from using charity money to help themselves. In particular, Trump appeared to use $258,000 from the charity to help settle lawsuits involving a golf course and an oceanside club. Trump also spent charity money to buy two portraits of himself, including one that he hung in the bar of one of his golf resorts in Florida.
"This is so bizarre, this laundry list of issues," said Marc Owens, the longtime head of the Internal Revenue Service office that oversees nonprofit organizations who is now in private practice. "It's the first time I've ever seen this, and I've been doing this for 25 years in the IRS, and 40 years total."
The laws governing the diversion of income into a foundation were written, in part, to stop charity leaders from funneling income that should be taxed into a charity and then using that money to benefit themselves. Such violations can bring monetary penalties, the loss of tax-exempt status, and even criminal charges in extreme cases.
Epshteyn, in the Saturday interview with The Post, said Trump did not knowingly violate any tax laws. "There's been no intent, in any way, to go against any applicable rules, laws, and regulations," Ephsteyn said. "If you suggest it any way otherwise, publicly, it's dangerous and irresponsible."
In an interview over the weekend, Trump offered a defense of his charity.
"Are you confident that the Trump Foundation has followed all charitable rules and laws?" journalist Sharyl Attkisson asked on a Sunday TV program called Full Measure.
"Well, I hope so," Trump said. "I mean, my lawyers do it."
The Trump Foundation has no paid staff. The last time it reported spending any money on legal fees was in 2010, when it spent $53 total for the year.
So far, questions about the Trump Foundation have focused on how the charity spent its money. How the charity raised money - especially after Trump stopped giving - was less understood.
Last week, an employee of the Trump Organization, the candidate's private company, offered an explanation.
"A lot of times Mr. Trump will give a speech somewhere or he'll raise money in some way and he asks that entity, instead of cutting a personal check to him, cut it to his charity," said Lynne Patton, an assistant to Trump's son Eric, who is also an officer of the Eric Trump Foundation. "That's money that otherwise would've been in his personal account, right?"
Patton was appearing at a Trump campaign event in Iowa, and was quoted in the Des Moines Register.
Under tax law, these kind of arrangements are called "assignment of income." A person is owed money, but instead of accepting the money, directs that it be given to another person or a charity.
But, tax experts say, the IRS generally requires that the person who was owed the money pay income tax on it. One key factor: Did the person exercise control over where their money went? If the money was directed to a specific recipient, it generally counts as income.
"You cannot take money that you earned, that's your income, and direct it elsewhere" without paying taxes, said Ellen Aprill, a professor at Loyola Law School in Los Angeles. "If you do it, you have to treat it as your income, and you have to pay tax on it first."
The Post asked the Trump campaign for examples of donations that matched Patton's account.
The Trump campaign initially responded that Patton's account was wrong.
"Lynne is wonderful," said Trump spokeswoman Hope Hicks during the Saturday telephone interview in which Epshteyn also participated. "But she is not a spokesperson for Mr. Trump or the campaign or the foundation."
After it was pointed out that Patton made the statement while appearing on behalf of the campaign, Hicks responded: "Yeah. ... She wouldn't know or understand."
Instead, Epshteyn put forward a different explanation. Trump, he said, had never done what Patton described.
That case involved a San Francisco bank president who had decided he had been paid enough and renounced the rest of his salary for the year. The bank gave his money to the University of California instead. The court held that the bank president didn't have to pay taxes on that money, because he hadn't controlled where it went.
Trump, Epshteyn said, was just like that. He had not exercised control over where his money went. Indeed, Epshteyn said, when Trump helped someone, he never asked specifically for a gift to the Donald J. Trump Foundation - but rather suggested a gift to some charity, somewhere.
But sometimes, Epshteyn said, a gift arrived at the Trump Foundation.
"He's Donald J. Trump," Epshteyn said, explaining why donors had chosen this particular charity.
Under the set-up that Epshteyn described, tax experts said, Trump might have escaped paying income taxes on donations to the Trump Foundation - as long as he truly had no influence over where the money went.
So which of the Trump Foundation's donations came in this way?
Epshteyn could not cite a specific example.
He then challenged The Post to find an example that proved him wrong.
The Post asked about the 2011 gift from Comedy Central. Back then, Trump had bragged on video that he was getting a big appearance fee. "They paid me a lot of money, and they were very generous. And all of that money goes to charity," Trump said.
After The Post brought up the Comedy Central case during the Saturday interview, Epshteyn conceded that Trump had, indeed, controlled where this money went.
It was his income. And, Epshteyn said, he paid taxes on it.
Could he provide proof of that tax payment?
"Absolutely not," Epshteyn said.
Epshteyn then challenged The Post to provide another example.
The Post offered the donations recorded from Ebers, who was the Trump Foundation's biggest donor in 2011, 2012, 2013 and 2014. Together, his gifts totaled $1.887 million.
The two people familiar with that arrangement said Ebers bought tickets and other goods and services from Trump. They said it was unclear if Trump himself or one of his employees instructed Ebers to pay the foundation instead of Trump.
The Post asked Ephsteyn and Hicks if Trump had paid taxes on the money received from Ebers. They did not answer the question, beyond saying that Trump had followed "all applicable rules and regulations."
New York Attorney General Eric Schneiderman, D, is investigating the Trump Foundation. If Schneiderman or the IRS were to find that Trump violated tax law, he could face civil penalties, such as fines, from either the state of New York or the IRS.
Tax-law experts say that more serious charges, such as income-tax evasion, are difficult to prove. One reason: in the world of tax law, ignorance is a defense.
"You have to prove that [a defendant] knew what the law was and willfully violated it anyway," said Jay Nanavati, a former tax prosecutor at the Justice Department, now in private practice. He said that merely proving wrongdoing was not enough: A defendant "can say, 'I did all this stuff. I meant to do all this stuff. And either I didn't know it was illegal, or a [lawyer] told me it was OK.' "
The only formal admission of wrongdoing by the Trump Foundation so far this year came when Trump paid a $2,500 penalty for an illegal $25,000 donation in 2013 to a political group controlled by Florida Attorney General Pam Bondi. The foundation has said the gift was an error, and Bondi has said it had no bearing on her office's decision not to pursue a fraud investigation of Trump University.
During the interview with Epshteyn on Saturday, The Post asked if the Trump Foundation had self-reported any other violations to the IRS or paid any other penalties.
"That's not something we're prepared to comment on," he said.