Jon Stewart Roasts Kevin O'Leary of 'Shark Tank

Stewart tackles investor reactions to Trump's fraud case verdict.

by Zain ul Abedin
Jon Stewart Roasts Kevin O'Leary of 'Shark Tank
© Kent Nishimura/Getty Images

In a recent episode of "The Daily Show," Jon Stewart delivered a pointed critique of Kevin O'Leary's comments regarding Donald Trump's civil fraud case in New York. Trump, the former president, was mandated by Justice Arthur Engoron to pay $464 million for inflating the value of his assets to secure bank loans and business deals.

Stewart, with his characteristic wit, outlined the case's proceedings and the repercussions of Trump's actions. Stewart humorously lambasted the naivety of those who might oversimplify the situation, stating, "You might be saying to yourself, well, that sounds pretty straightforward.

Whatever gains you got from lying, you have to pay back." He then jestingly called such individuals "idiots" before diving into the media's portrayal of the trial.

O'Leary's Investor Fears

Highlighting a segment from a CNN interview, Stewart showcased "Shark Tank" star Kevin O'Leary expressing concern over the verdict's reception within the investment community.

O'Leary's apprehension, "We're all asking each other, who's next?" prompted Stewart to mockingly sympathize with the "persecuted minority" of investors, while also branding O'Leary as notably disagreeable, even among his co-stars on "Shark Tank." O'Leary, who joined the reality show in 2009, is notorious for his harsh criticism of contestants' business valuations.

Stewart expressed astonishment at O'Leary's defense of asset inflation, contrasting it with his televised reprimands of entrepreneurs for overestimating their company's worth. The comedian used clips from "Shark Tank" to highlight O'Leary's contradictions, showcasing his disbelief at overly optimistic business valuations.

Stewart further criticized the broader implications of asset inflation, stressing the ethical breaches and systemic corruption it fosters. By showcasing another snippet from O'Leary's interview, where he defends the practice as commonplace among real estate developers, Stewart drew boos from his audience.

He likened O'Leary's justification to the premise of the 2013 horror film "The Purge," mocking the absurdity of legalizing a crime due to its widespread commission. Ending on a serious note, Stewart emphasized the consequences of such fraudulent behavior, underscoring the real victims of these actions and the systemic corruption it perpetuates.

Through his analysis, Stewart not only highlighted the discord between O'Leary's public persona and his stance on ethical business practices but also critiqued a broader culture of entitlement and legal impunity in the face of clear wrongdoing.