The question was once again brought into sharp focus Wednesday by the release of Trump's annual financial filing with the Office of Government Ethics, which requires top officials to disclose their assets, income and liabilities.
At issue is whether the payment to Daniels was a personal legal expense or a loan from Cohen that would benefit the Trump campaign in the final weeks of the race against Democrat Hillary Clinton.
Following initial denials from Trump that he knew of the payment, the president's recently hired attorney, former New York City Mayor Rudy Giuliani, told Fox News host Sean Hannity earlier this month that Trump had reimbursed Cohen and that the payment was "perfectly legal" and did not violate campaign finance law.
"It's not campaign money. No campaign finance violation. They funneled through a law firm and the president repaid it," Giuliani said.
In a separate interview the next day on the Fox News program "Fox & Friends," Giuliani insisted the hush money was paid "for personal reasons."
"The president had been hurt personally, not politically, personally so much — and the first lady — by some of the false allegations," he said. "That one more false allegation 6 years old, I think [Cohen] was trying to help the family."
But later in the same interview, Giuliani conceded that the payment clearly had a political component.
"Imagine if that came out of Oct. 15, 2016, in the middle of the last debate with Hillary Clinton?" he said. "Cohen made it go away. He did his job."
Trump's annual financial filing, released Wednesday, includes conflicting characterizations of the Cohen payments.