Jon Stewart Lays Into ‘Shark Tank’ Judge Kevin O’Leary for Comments on Trump Fraud Case

Jon Stewart’s weekly slot behind the Daily Show desk on Monday saw the host eviscerate Canadian mogul and Shark Tank judge Kevin O’Leary for comments he made indicating that Donald Trump and his company were unfairly targeted by New York state, which issued a punishing penalty against the former president in a civil fraud case.

Following the harsh judgment leveled by Judge Arthur Engoron in the case led by New York Attorney General Leticia James, Trump had been staring down a Monday deadline to raise enough cash to pay a $454 million bond. But on Monday, that figure was reduced at the eleventh hour by the state’s appellate court, and now Trump and his associates must fork over $175 million within 10 days of the ruling. Trump has said he will pay this amount, indicating in a Truth Social post that he has $500 million; if he does not pay the penalty, James has said she could execute the state’s right to seize some of the former president’s assets.

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James’ investigation found that, for a decade, the Trump Organization would illegally inflate the value of its real estate holdings while seeking loans. After the appellate court’s decision, Trump said in a statement that the reduction “shows how ridiculous and outrageous” the $454 million judgment is. O’Leary, in a recent appearance on CNN to discuss that penalty, agreed with the former president.

“That didn’t go over very well with the investment community because we’re all asking each other, ‘Who is next?’” O’Leary said in a clip.

That quote from O’Leary’s interview concluded a montage compiled by The Daily Show of cable news guests commenting on the case, with the businessmen calling the decade of fraud committed by the Trump Organization a “victimless crime” that is “blatantly unfair.” Stewart laid into this set of investors and singled out O’Leary, mocking the notion of a put-upon “investment community” while commenting on the reputation cultivated by the CEO.

“I am surprised to hear this from Kevin O’Leary,” Stewart told the audience. “He’s a guy who’s such an asshole … even the other people on Shark Tank think he’s an asshole. I’m surprised to hear that he’s so chill about overvaluing something that he thinks is victimless, because when someone tries to do that to him …”

The show then cut to a montage of O’Leary angrily mocking the valuations that Shark Tank entrepreneurs have indicated for their startups: “Your valuation is insane. Your valuation is crazy. I think that’s a crazy valuation. I think your valuation is stinky poo-poo,” O’Leary was heard saying in the mashup of clips.

Stewart questioned why O’Leary would not get as hopping mad as he was in these moments on Shark Tank when it comes to overvaluations such as the ones committed by Trump — which was never victimless, as the comic pointed out.

“First, the banks got paid back at lower interest rates — although to be honest, who gives a shit?” Stewart said. “But second, money isn’t infinite — a loan that goes to the liar doesn’t go to someone who’s giving a more honest evaluation. So, the system becomes incentivized for corruption … avoiding taxes hurts all of us. Donald Trump’s shenanigans cost the city of New York, to be honest.”

O’Leary was quoted from the same CNN interview, with host Laura Coates challenging his notion that James’ office had no business going after Trump and the widespread fraud his organization committed, indicating that breaking laws like falsifying business records, insurance fraud and conspiracy are actual crimes. The head of O’Leary Ventures, a venture capital investment company, replied that, as far as he’s concerned, Trump isn’t alone in such business practices.

“Everything you just listed off is done by every real estate developer everywhere on earth, in every city,” he snapped back. “This has never, ever been prosecuted.”

O’Leary’s candor on this didn’t escape Stewart’s acid tongue — as the host took the CEO’s gall to task.

“There is a theory in law that if enough people commit a crime, it automatically becomes legal,” Stewart sarcastically quipped, before getting serious. “The fucking entitled arrogance. I don’t know if you know this, but most people just kind of commit fraud and expect to face no repercussions. Even if everyone’s doing it; try getting a car loan by saying you have 10 times as much money as you really do. Or claim 20 dependents when you have no children. Or say you make slightly less money to qualify for food assistance — I will guarantee you, there are not just financial consequences for those lies, but criminal ones.

“But don’t tell that to the investment community, because in their minds in pursuit of profit, there is no rule that cannot be bent. There is no principle that can not be undercut, as long as you and your friends are making money.”

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