Veteran late-night host Jon Stewart weighed in on the drama surrounding former President Donald Trump’s civil fraud case during a Monday night broadcast, calling Trump a “liar” for allegedly overinflating the value of his New York real estate holdings. However, according to an exclusive report from the New York Post, Stewart once did the exact same thing, netting a staggering 829 percent return on the sale of his Tribeca penthouse apartment.
As Valuetainment previously reported, Judge Arthur Engoron ruled that former President Trump deliberately overstated his net worth to mislead creditors and secure more favorable loans for his New York businesses. During the initial trial, Trump argued that there were no actual victims of the alleged deception given that every lender had been paid back in full. His attorneys have maintained this defense in the ongoing process of appealing the $464 million penalty.
However, during Monday’s episode of “The Daily Show,” Stewart claimed that, contrary to expert opinions, these were far from “victimless crimes.”
“Money isn’t infinite. A loan that goes to the liar doesn’t go to someone who’s giving a more honest evaluation,” Stewart declared. “So the system becomes incentivized for corruption.”
“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,” he added. “It was all part of a very specific real estate practice known as lying.”
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But within hours of Stewart’s monologue, internet sleuths uncovered a remarkably similar situation in the comedian’s own business history.
As reported by The New York Post, in 2014, Stewart sold a 6,280-square-foot duplex for $17.5 million to financier Parag Pande. But according to assessor records from the previous year, the property’s estimated market value was only $1.882 million. The actual assessor valuation placed it even lower at $847,174.
Additional records show that Stewart used this drastically reduced assessor valuation to lower his property taxes—exactly the same method used by former President Trump.
Pande eventually resold the property in 2021 for $13 million, a loss of 26 percent.
Meanwhile, reduced assessor valuations served as the exact same metric used by New York Attorney General Letitia James in her civil suit against Trump. Citing the low assessments, James claimed that Trump had lied about the value of his properties, which include Trump Tower in New York and Mar-a-Lago in Palm Beach, Florida.
However, when the media discussed the possibility of Trump being forced into a “fire sale” to cover the $464 million bond payment, these same properties were suddenly valued in the hundreds of millions once again.
Connor Walcott is a staff writer for Valuetainment.com. Follow Connor on X and look for him on VT’s “The Unusual Suspects.”
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