"Late Show" host Stephen Colbert on Monday examined a recent New York Times report revealing that Donald Trump declared nearly a billion dollars in losses on his federal income tax returns in 1995.
According to the Times report, the Republican presidential nominee declared a $916 million loss — "through mismanagement of three Atlantic City casinos, his ill-fated foray into the airline business and his ill-timed purchase of the Plaza Hotel in Manhattan" — which would legally allow him to avoid paying any federal income tax for up to 18 years.
"That is right," Colbert said. "Donald Trump lost money on casinos. You know what they say — the house always loses."
"Now, the idea that Trump hasn't paid taxes [in] nearly 20 years is bound to be unpopular with — what's the word? Uh, people," he continued. "But according to the former mayor Rudy Giuliani ... Trump not paying taxes just proves how smart he is."
In an interview with CNN on Sunday, Giuliani called Trump a "genius" for hiring a team of accountants and, in absentia, taking advantage of the tax loophole.
"Yes, only a genius could lose a billion dollars running a casino," Colbert responded. "How loose were his slots?"
Then, on "Meet the Press," Giuliani said, "A lot of the people who are poor take advantage of loopholes and pay no taxes. Those are loopholes also. And they pay no taxes."
"Yes, those crafty poor people," Colbert responded again. "And don't get me started on the cunning homeless who have found a way around property tax."