In the high-stakes world of New York City real estate, the line between assessed and market value can get blurred. In a civil fraud case involving former President Donald Trump, centers around allegations he overvalued NYC property.

"Daily Show" host, John Stewart challenged O'Leary's assertion that overvaluation was a victimless crime, arguing that it can have real consequences for investors, interest rates and the broader economy.

He further remarked, “Donald Trump’s shenanigans cost the City of New York.”

Stewart has been vocal in his criticism of Trump's alleged overvaluation of assets. He recently blasted “Shark Tank” star Kevin O’Leary over the Trump case. But then questions about Stewart's own property dealings surfaced.

In a post on X, podcaster Tim Pool shared a New York Times headline dating back to 2014, which announced, “Jon Stewart Sells TriBeCa Penthouse for $17.5 Million.”

Pool raised a question, “Did @jonstewart commit fraud when he sold his penthouse for $17.5M? NY listed its market value at $1.8M an AV at around 800k. Who did he defraud?? I am SHOCKED.”

Pool’s post had garnered 2.1 million views, along with over 40,000 likes and close to 10,000 reposts.

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Overvalued NYC Property

The focus was on a Tribeca penthouse once owned by Stewart, which he sold for a staggering $17.5 million in 2014.

Assessors had pegged the property's market value at a mere $1.882 million. Websleuths did the math, claiming Stewart may have overvalued the property by 829%.

The discrepancy between the assessed value and the sale price has raised eyebrows and prompted questions about the ethics of property valuation in the city's competitive real estate market.

Critics argue that such disparities can distort market perceptions and contribute to inflated property prices.

Stewart Real Estate Deal

Stewart's sale of the Tribeca penthouse, while lucrative, underscores the unpredictable nature of real estate transactions.

The substantial difference between the assessed value and the sale price highlights the role of buyer perception and market dynamics in determining property values.

The property was later resold in 2021 for just over $13 million, representing a 25% decrease from the purchase price. This decline underscores the volatility of the real estate market and subjectivity of what a property may be worth.

Stewart Responds

His response to Pool on X got 8 million views.

“OMG!! I've been caught doing something not remotely similar to Trump! I guess all I need to do now is start a fraud college, steal classified docs, bankrupt casinos, pay hush money, grab pussies, discriminate in housing, cheat at golf and foment insurrection and you'll revere me!”

The fact remains that the NYC case where Trump has been asked to pay 1/2 billion dollars in fines is about overvaluing his properties to a bank in order to get a loan.

And a disclaimer was included with the application encouraging the bank to do their due diligence of the values.

The bank’s officers testified that it was a standard loan and was repaid in full.

And surprisingly, Stewart's 2014 sale price of the Tribeca penthouse is actually more than a judge decided in the Trump case, Mar-a-Lago in Florida is worth today.

Some have accused Stewart of hypocrisy, pointing to his own property dealings as evidence of a double standard. And New York Mayor has attempted to reassure the city that no one else will be prosecuted under the rather obscure law.