5 Times Trump Bragged About His Shady Business History In The Debate

September 27, 2016 11:47 a.m.

When it came to Donald Trump’s self-proclaimed business acumen, Hillary Clinton at the Monday’s presidential debate had a plan: Take what he believes is his greatest asset and turn it into a liability, in the form of a reminder of the shady, scummy and maybe illegal things he did on the way to building his empire. And Trump couldn’t help but play into her hands. Any time she brought a business practice or comment that would prompt others to show remorse, Trump responded glibly–or even bragged about it.

Here are some examples:

You Didn’t Pay Your Taxes: ‘That Makes Me Smart’

Clinton floated a number of theories that could explain why Trump wouldn’t release his tax returns, not the least of which being the possibility that he did not pay federal income taxes. She pointed to a few years of returns that have been seen by others — when he was applying for a casino licenses — that showed no federal income taxes were paid.

“That makes me smart,” Trump interjected.

Later on in the debate, Clinton brought up the allegation again, as Trump blamed the country’s poor state on money being “squandered” on Clinton’s “ideas.”

“And maybe because you haven’t paid any federal income tax for a lot of years,” Clinton shot back.

“It would be squandered, too, believe me,” Trump said, without denying that her claim could be true.

You Cheered On The Housing Crisis: ‘That’s Called Business’

Clinton brought up remarks she said Trump made in the mid-2000s rooting for a housing crisis.

“In fact, Donald was one of the people who rooted for the housing crisis. He said, back in 2006, ‘Gee, I hope it does collapse, because then I can go in and buy some and make some money.’ Well, it did collapse,” she said

Rather than deny the characterization. Trump bragged, “That’s called business, by the way.”

You Were Sued For Discrimination: ‘Many Other Companies … Were Sued’

After Trump showed little regret over his birther campaign, Clinton referenced lawsuits his family’s businesses faced for allegedly discriminating against African Americans. Trump did little to push back on the claim that they engaged in discriminatory behavior and rather brushed off the lawsuit as something other companies faced.

“Now, as far as the lawsuit, yes, when I was very young, I went into my father’s company, had a real estate company in Brooklyn and Queens, and we, along with many, many other companies throughout the country — it was a federal lawsuit — were sued,” Trump said. “We settled the suit with zero — with no admission of guilt. It was very easy to do.”

You Didn’t Pay Your Contractors: ‘Maybe He Didn’t Do A Good Job’

Clinton pointed out an architect in the debate audience who she said Trump resisted paying after he designed Trump a golf club house.

“Maybe he didn’t do a good job and I was unsatisfied with his work,” Trump said, shrugging off the allegation.

You Got A $14 Million Loan From Your Dad: It Was ‘A Very Small Loan’

From the get-go, Clinton went after Trump’s claimed image as a self-made man and casually mentioned the $14 million loan he took from his dad at the beginning of his career. Trump couldn’t let the reference go and tried to explain it away as a “small loan.”

“Well, for one thing — and before we start on that — my father gave me a very small loan in 1975,” Trump said, “and I built it into a company that’s worth many, many billions of dollars.”

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