Republican presidential candidate Donald Trump has dealt with some legal blows in recent years, from fraud allegations related to Trump University to fines against one of his resorts. The Washington Post reports that Trump used $258,000 of funds from his charity, the Donald J. Trump Foundation, to settle costs for his for-profit businesses. 

The use of more than a quarter of a million dollars in charitable funds may violate "self-dealing" laws, according to the Washington Post, which dictates that not-for-profit leaders are not allowed to use charity funds for their personal or for-profit venture benefit.

$100,000 of these funds were spent when the Trump-owned Mar-a-Lago Club in Palm Beach, Fla. in 2007. The Club faced a $120,000 fine because of the size of one of their flagpoles, but the fine was settled when Trump agreed to donate $100,000 to a charity for veterans. The Washington Post reports that the check Trump used for the donation was cut by the Donald J. Trump Foundation. 

The Washington Post further reported that another $158,000 of Trump Foundation funds were were spent similarly when Trump agreed to settle a suit against one of his New York golf courses by making a donation to a charity of the plaintiff's choosing. 

Most egregiously and in true Trump fashion, the GOP contender for president spent $20,000 to buy a 6-foot-tall portrait of himself. But that wasn't the only time Trump used charitable dollars to buy his own portrait. The Post found that Trump also bought a portrait of himself for $10,000 at a 2014 charity fundraiser, for a total of $30,000 in charitable funds spent on portraits of himself. Another $5,000 were used to buy ads for Trump's hotels in 2013. 

The Post reports that if the IRS finds Trump to be in violation of self-dealing laws, he would be required to either refund all of the foundation's money that he spent, or pay penalty taxes. 

Jeffrey Tenenbaum, a lawyer who advises nonprofits at the Venable law firm told the Washington Post, "If he’s using other people’s money—run through his foundation—to satisfy his personal obligations, then that’s about as blatant an example of self-dealing [as] I’ve seen in a while." Tenenbaum added that in all his dealings with nonprofit groups (which he cited at 700 per year), he'd "never encountered anything so brazen."