"Late Night with Seth Meyers"/NBC; Hulu
Meyers' theory arrives after Trump found himself in yet another controversy over his taxes. Someone leaked The New York Times Trump tax records from 1995, and the newspaper asked tax experts to evaluate them. What it found was that he reported business losses of about $916 million, which would've provided him a way to skip paying taxes for 18 years.
The report brings into doubt Trump's record of giving back to society, his business acumen, and how much he's worth.
"Here's why this latest revelation is so damning," Meyers said on Monday's "Late Show." "First of all, there's the fact that Trump has consistently sold himself as a brilliant businessman, who could use those skills to fix the economy."
The story showed that investors in Trump's company saw their shares go from $35.50 to just 17 cents, while Trump made $45 million in income.
"Normally to get that screwed, you have to actually go into the casino," Meyers joked. "And at least then, they have the dignity to give you free drinks. So Trump's investors lost more than 90% of their money in a year when the stock market went up. It would have gone better if they just picked stocks at random."
Yet Trump continues to refuse to release his most recent tax returns. Meyers wonders why. What could they contain that's worse than a $916 million loss? That led to him explaining his theory.
"I think you're poor," the host said, addressing Trump directly. "I think you pretend to be rich, but you've been going town-to-town for months selling cheap hats."
Watch Meyers explain his theory below: