“You have to pay back”: Jon Stewart slams Shark Tank's Kevin O'Leary over Donald Trump comment

Jon Stewart, the political commentator and television host, recently called out the Canadian business mogul and Shark Tank judge Kevin O'Leary for his comments about Donald Trump's New York State fraud case.

The former president was asked to pay a $454 million bond by Judge Arthur Engoron in a case led by Attorney General Leticia James. However, on Monday, March 25, the payment was reduced to $175 million, which must be paid within 10 days of ruling. Kevin O'Leary spoke about the topic in a CNN interview, asking the "investment community" about "Who is next?"

The Daily Show host went on to reply to conservatives' defense of Trump's "victimless crime" by posting a montage of interviews. He began by explaining to the audience what Trump's case is about and then spoke about O'Leary, saying,

"You might be saying to yourself, well, that sounds pretty straightforward. Whatever gains you got from lying, you have to pay back. I am surprised to hear this from Kevin O’Leary. He’s a guy who’s such an a*sh*le, even the other people on Shark Tank think he’s an a*sh*le. 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 montage changed to Kevin angrily berating entrepreneurs who made evaluations of their businesses that were not agreeable to the mogul.

---

Jon Stewart mocks Kevin O'Leary for claims about Donald Trump's New York City fraud case

During the Monday episode of The Daily Show, Jon Stewart went on to speak about Donald Trump's $175 million bond case. Leticia James, the New York Attorney General, has been investigating the Trump Organization for over a decade. The attorney found that Trump and his team would illegally inflate the value of his real estate holdings and then seek loans for them.

After the state’s appellate court reduced the amount of the bond from $454 million to $175 million, the former president said that he could pay the amount because he had $500 million. He also added that the reduction "shows how ridiculous and outrageous" the initial judgment was.

Several cable news guests sided with Trump, and Jon Stewart made a compilation of them all while mocking them. He then singled out Kevin O'Leary, adding his clips about Shark Tank evaluations where the judge called out the entrepreneurs, saying,

“Your valuation is insane. Your valuation is crazy. I think that’s a crazy valuation. I think your valuation is stinky poo-poo.”

As the audience laughed, Jon Stewart also pointed out why Kevin was not enraged by Trump's overvaluations. He also said that the fraud case was not victimless. The comedian explained,

“First, the banks got paid back at lower interest rates — although to be honest, who gives a sh*t? 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.”

The mashup added another clip of O'Leary talking about Trump's widespread fraud. CNN host Laura Coates said breaking laws like making false business records, insurance fraud, and other conspiracies are actual crimes. O'Leary responded that several other businesses commit the same crimes. He said,

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

Kevin O'Leary is the head of O'Leary Ventures, and he spoke at length about how Attorney James' office should not have prosecuted or investigated Donald Trump. To which Jon Stewart responded,

“There is a theory in law that if enough people commit a crime, it automatically becomes legal. The f*cking entitled arrogance. I don’t know if you know this, but most people just kind of commit fraud and expect to face no repercussions.”

The host then talked about various methods to get loans through fraud, such as saying one has 10 times more money than one actually does. However, he warned the audience that there are indeed consequences for the same, unlike what Kevin said, and they are not just financial but criminal. He added,

“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 cannot be undercut, as long as you and your f*cking friends make money. And the only immoral practice, apparently, in the capitalist system is to use that money for people who may need it.”

Jon Stewart concluded his monologue by sarcastically quipping that "stealing is only justified when you already have too much."

The comedian's next The Daily Show episode will come out on Wednesday, March 27, 2024.