Joe Raedle/Pool via AP
During the political showdown at Hofstra University, Democratic nominee Hillary Clinton said "there is something" Trump "is hiding" in his tax returns, which is why he refuses to release them publicly, a tradition that every major party presidential candidate has followed for 40 years.
"Or maybe he doesn't want the American people, all of you watching tonight, to know that he's paid nothing in federal taxes, because the only years that anybody's ever seen were a couple of years when he had to turn them over to state authorities when he was trying to get a casino license, and they showed he didn't pay any federal income tax," she said.
"That makes me smart," Trump fired back.
The answer raised plenty of eyebrows, with many questioning whether the Republican nominee was admitting to not paying federal income taxes.
Clinton pressed on, adding that "maybe ... you haven't paid any federal income tax for a lot of years."
"It would be squandered ... believe me," the Republican nominee said.
After the debate, Trump told CNN "of course I've paid federal taxes."
But that didn't stop his surrogates from being hit with a bevy of questions about his tax history, which has stayed in the news cycle as Trump's insisted that he cannot release his taxes publicly while he said they're under a routine audit by the Internal Revenue Service. He's previously said that audit may or may not be completed ahead of the election.
"Listen, he was making a side comment," GOP chair Reince Priebus said following the debate. "He did that throughout the night. What he was talking about was making sure that, you know, he's not paying too much in taxes. But I thought he handled that right."
Sara Huckabee Sanders, a prominent Trump supporter and daughter of former Arkansas Gov. Mike Huckabee, went along a similar path as Priebus, calling it an "off-handed comment," adding she "didn't catch the exact context."
The comment was roundly ripped by Clinton's surrogates.
Billionaire businessman Mark Cuban, a Clinton-backer who had a front-row seat to the event, has ripped Trump repeatedly on social media and in interviews about his refusal to release the returns.
"Look, at some point you have to respect the fact that you're American and you have an obligation to contribute to our society," he told Business Insider after being asked about Trump's comment from the debate.
Brian Fallon, the spokesman for Clinton's campaign, said the remark proved Trump is out of touch with everyday Americans - the same portrayal many Democrats used in 2012 to describe then-GOP nominee Mitt Romney, who faced immense pressure to release his taxes as well.
However, Romney did release his taxes.
"I think he came off as a Romney-style plutocrat," Fallon told Business Insider. "He defended the idea of not paying taxes was a smart move."
But Rep. Chris Collins of New York, one of Trump's biggest backers in Congress, called the demands to see Trump's taxes a "witch hunt" and added he definitely shouldn't released them with just six weeks before election day. He thought Trump's answer about being "smart" was completely appropriate.
"What I would say is every American, Hillary Clinton, you, me, Donald Trump, pays the minimum amount of taxes we're required to pay under an 8,000 page tax code," he said following the event. "Mitt Romney or Barack Obama or Donald Trump."
"I don't know what taxes he pays, because in real estate you have depreciation, so again I don't know what he pays and I'm not sure it matters because I'm sure he pays the least amount that he has to like every American, which is why this whole tax return thing is a lot of nonsense," he continued.
He said, should Trump release his taxes now, it "would create more problems" because "everybody would be pouring through them and nitpicking."
"And, God knows how many pages they are," he added. "And [people would] say 'why didn't he give more money here? what happened with this partnership?' with six weeks to go."
"I don't think anyone should release their tax returns," he continued, later adding "I'm just glad when Donald Trump doesn't release them we'll be done with this once and for all."