Hillary Clinton Pounds Away at Donald Trump's Mysterious Tax Record

Hillary Clinton is hammering Donald Trump over his tax record, sensing a chance to turn a successful debate encounter into a decisive campaign issue.

With her Republican rival refusing to release his tax returns, she is filling in the blanks herself by offering up the least charitable interpretation: that the Republican has exploited the system to avoid paying taxes.

"He actually bragged about gaming the system to get out of paying his fair share of taxes," the Democrat told supporters Tuesday in Raleigh, N.C. "In fact, I think there's a strong probability he hasn't paid federal taxes a lot of years."

She expanded upon the attack by making a moral case for paying taxes to support veterans and other important institutions.

"He probably hasn't paid a penny to support our troops our our vets or our schools or our health care systems. And when I confronted him with the reasons why he won't release his tax returns — and I got to that point where I said maybe he's paid zero — he said maybe that makes him smart," she said. "Now, if not paying taxes makes him smart, what does that make the rest of us?"

At the debate, Clinton said Trump may be hiding his returns because "he's not as rich as he is" or because "he's paid nothing in federal taxes." Trump interjected: "That makes me smart." She repeated the charge moments later that he hasn't "paid any federal income tax for a lot of years." Trump interrupted again: "It would be squandered, too, believe me."

The pro-Clinton super PAC Priorities USA piled on with a new digital ad on Wednesday called "$0 In Taxes," highlighting that moment from the debate.

A Trump campaign spokesperson didn't immediately return a request for comment.

At the debate, he changed the topic to a policy distinction between the candidates: "I'm going to cut taxes big league, and you're going to raise taxes big league," Trump said. "End of story." Trump's plan would lower taxes by trillions of dollars, with the largest gains going to upper incomes, while Clinton has proposed a variety of tax increases for the highest earners.

Every major party nominee since the late 1970s has released his or her tax returns before the election. Trump has refused, saying his lawyers have advised him not to do so because he's under audit, although that does not legally bar him from making his returns public. Hillary Clinton has released 39 years of tax returns, disclosing her 2015 return in August. In 2012, Republican Mitt Romney initially declined to disclose his latest tax returns, then caved under pressure in September. Trump himself urged Romney to do so and Romney, this year, has asked Trump to do the same.

During the Republican primary, Trump openly boasted that he exploited a broken system to benefit himself and his businesses, but promised that, as president, he'd use his inside knowledge of the system to fix it for ordinary Americans. The pitch helped win him the nomination, but Clinton is betting his claim will fail with the broader electorate. 

Trump, meanwhile, is continuing to paint himself as a savvy businessman ready to use his chops in service of the country.

"I have a great company. I have a tremendous income. And the reason I say that is not in a braggadocious way. It's because it's about time that this country had somebody running it that has an idea about money, when we have $20 trillion in debt, and our country's a mess," Trump said at the Hofstra University debate. "It's politicians like Secretary Clinton that have caused this problem."