The cases involved a combined $258,000 paid out by the Donald J. Trump Foundation – a charity almost entirely funded with other people’s money, the newspaper said – and follow a review of legal documents and the foundation’s tax records.
The newspaper carried out a long investigation into the charity’s finances, finding that Trump himself has not contributed a dollar since 2009. The group is funded by donations from third parties instead.
One of the group’s suspect payments was a $100,000 donation to a veterans’ charity in 2007 as part of a legal settlement with the city of Palm Beach, Florida.
Trump had sued the city after it fined him $120,000, or $1,250 per day, for erecting an 80-foot (24-meter) flagpole at his Mar-a-Lago Club that exceeded the maximum 42 feet permitted by local regulations.
The Trump Foundation also made transactions that appeared to be exclusively for the benefit of the real estate mogul or his businesses, apparently in violation of regulations governing charities, the Washington Post said.
In one case, the charity paid $20,000 in 2007 for a six-foot portrait of Trump, the newspaper reported.
“Clearly the Trump Foundation is as much a charitable organisation as Trump University is an institute of higher education,” said Christina Reynolds, a spokeswoman for the campaign of Trump’s White House rival, Democrat Hillary Clinton.
“Once again, Trump has proven himself a fraud who believes the rules don’t apply to him,” she said in a statement.
“It’s past time for him to release his tax returns to show whether his tax issues extend to his own personal finances.”
Some Democrats have complained that the media has not sufficiently reported about the Trump Foundation’s suspected wrongdoing, accusing journalists of being lenient in their treatment of the outspoken billionaire.
Trump’s campaign denied the Post report.
“In typical Washington Post fashion, they’ve gotten their facts wrong. It is the Clinton Foundation that is set up to make sure the Clintons personally enrich themselves by selling access and trading political favours. The Trump Foundation has no paid board, no management fees, no rent or overhead, and no family members on its payroll,” said spokesman Jason Miller.
News outlets have also been criticised for being more keen to cover a tweet by Trump’s son comparing Syrian refugees to a bowl of colourful Skittles candy.
“If I had a bowl of skittles and I told you just three would kill you. Would you take a handful?” he wrote. “That’s our Syria refugee problem.”
“If you are covering Skittles-gate instead Trump’s illegal use of his foundation, you are probably in journalism for the wrong reasons,” tweeted Dan Pfeiffer, a former top advisor to President Barack Obama.