7 Times Jon Stewart Blasted Donald Trump

Donald Trump was slapped with a new issue after he and his company were ordered to pay $464 million to a New York court. He was given a choice to post a bond to appeal.

In an episode of The Daily Show, Jon Stewart commented on the ordeal and declared the Trump Organization "died as it lived — fraudulently."

"What did Trump actually do to earn this penalty? Well it turns out that for a decade, whenever Trump wanted to get a loan or get a deal, he would illegally inflate the value of his real estate, for instance suggesting that his 11,000 square foot penthouse was a 30,000 square foot penthouse — I guess somehow including the sky in the calculation," he said.

Stewart added, "And the attorney general of New York knew that Trump's property values were inflated, because when it came time to pay taxes, Trump undervalued the very same properties. It was all part of a very sophisticated real estate practice known as lying."

The bond is due by the end of March, and Trump's lawyers said the former president approached 30 underwriters to back the amount.

In 2018, Stewart delivered an eight-minute message to Trump when he appeared as a guest on The Late Show with Stephen Colbert. The comedian called out the former POTUS for his "gleeful cruelty" before highlighting the issues of immigration and Trump's policy of separating children from their parents at the U.S.-Mexico border.

"Donald, you could have absolutely made a more stringent border policy, that would have made your point about enforcement, but I guess it wouldn't have felt right without a Dickensian level of villainy," he stated.

Stewart ended his speech by saying, "And by not yielding we will prevail. Unless, of course, the Democratic leadership continues to be a bunch of feckless…"

Stewart appeared at New York's Radio City Music Hall in 2017 to join Dave Chappelle's residency. He took his time to discuss the white supremacist tropes' riots in Charlottesville, Va., and accused Trump of being a terrible person.

"I don't think everybody who likes him is a Nazi but everybody who is a Nazi sure does seem to like him," he continued, adding he was not surprised by Trump's behavior.

Ahead of the 2024 presidential election, Trump created a new term using "migrant crime" and began using the word "Bigrant crime" — linking Joe Biden's name.

"It's a portmanteau," Stewart mocked Trump, adding he was not completely sold on the word. "It really just sounds like a migrant who's open to crossing either border."

Speaking on Fareed Zakaria GPS, CNN's Fareed Zakaria asked Stewart whether Trump should be indicted over the scandal.

"The law should always take into account someone's popularity," he answered. "What's happened to our country? It's as though you can't even commit financial fraud anymore. You can't inflate the value of your properties when you need a loan and then deflate it with taxes."

Stewart added, "I mean, the next thing you know, they're going to send you to jail instead of your lawyer, and your accountant, and your campaign manager, and everyone else around you The idea that someone may face accountability who's that rich and powerful is outrageous, and this country shouldn't stand for it."

If an indictment only makes people support Trump more, Stewart said it only means "we either have the rule of law, or we have no rule of law."

Despite Trump's legal issues, Stewart admitted he does not see the businessman going to jail.