Stephen Colbert questions Donald Trump's business 'genius' after taxes leak

Stephen Colbert questions Donald Trump business "genius"
(Image credit: Late Show)

Stephen Colbert began Monday night's Late Show by wishing a happy 5777 to his Jewish viewers, blowing a shofar and remarking about how terrible dead ram's horns smell before doing an awkward bit about a sexy rabbi calendar. Then he got to the part his audience was waiting for: the New York Times report on Donald Trump's leaked 1995 tax returns, where he wrote down a $916 million loss over the collapse of three mismanaged Atlantic City casinos. "Donald Trump lost money on casinos," Colbert gawked. "You know what they say: The house always loses."

That massive loss allowed Trump to legally avoid paying federal income tax for 18 years, Colbert noted. "Well, when life gives you lemons, don't pay taxes," he said. "Now, the idea that Trump hasn't paid taxes in nearly 20 years is bound to be unpopular with — what's the word? — people." On the other hand, Trump supporters like "the former Rudy Giuliani" argue that Trump is a "genius" for using the tax code to his benefit — an idea Colbert found amusing: "Yes, only a 'genius' could lose a billion dollars running a casino. How loose were his slots?"

And the idea that Trump can use his experience to fix the tax system was puzzling, too. "When you think about it, it's not like Donald Trump does his own taxes," Colbert said. "Shouldn't we really be voting for his accountant, Jack Mitnick? Because let's face it, Mitnick — there's just something about 'Mitt' that screams 'presidential.'" He took umbrage at Giuliani's comparison of Trump not paying taxes with Americans too poor to meet the income-tax threshold — "Yeah, those crafty poor people — you know those poor people with their loopholes. And don't get me started on the cunning homeless, who have found a way around property tax" — and arched an eyebrow at Trump's "free-form poetry slam" rally on Saturday night, marveling at Trump's noun-less word salad: "But then, being a demagogue is like jazz — it's the racism you don't say." Watch below. Peter Weber

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Peter Weber

Peter Weber is a senior editor at, and has handled the editorial night shift since the website launched in 2008. A graduate of Northwestern University, Peter has worked at Facts on File and The New York Times Magazine. He speaks Spanish and Italian and plays bass and rhythm cello in an Austin rock band. Follow him on Twitter.