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Jon Stewart Mocks Donald Trump Reportedly Profiting $2B During His Presidency On Michelle Obama's Podcast After 'Grifter' Claims: 'You Guys Left Money On The Table'

August 30, 2026 by Julia DeKorte
shefinds | Celebrity

Jon Stewart appeared on Michelle Obama’s podcast earlier this week, and the conversation naturally turned to comparing the Obama’s time in office to the Trump family’s time in office, namely their financials. Since Donald Trump assumed the presidency about a year and a half ago, he has increased his net worth by billions. In 2025 alone he added about $2.2B to his net worth—far more than the previous year, when he reported earning about $600M. Jon joked with Michelle that she and Barack missed out on a real opportunity for profit. Keep reading for more information.

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Jon Stewart Calls Out Trump On Michelle Obama's Podcast

On August 26th, Jon Stewart appeared on Michelle Obama and Craig Robinson's IMO podcast, and he asked the former first last lady what it's been like having the Trump family as their successors. "“I imagine for you and your family…that it’s a surreal experience for you guys because of the effort that you put into building something up and to watch it be corrupted," Jon said. "Although I have to say, you guys left money on the table," he joked, referencing the wealth the Trumps have gained through the presidency.

Michelle replied, "I didn’t even know it was possible; there were so many things" that they could've done to make money off their status as the first family.

"You guys didn't do a pump and dump," Jon said. "You left some money on the table."

"It’s the level of corruption that is, in some ways, maybe it’s doing a favor by making the current power structure and dynamic of this country untenable because of how explicitly corrupt," he added.

donald trump

Donald Trumps Increases His Wealth By Over $2B In One Year

According to Trumps' annual financial disclosure released earlier this year, he reported earning more than $2.2B in 2025, which is quite the dramatic jump in numbers from the $600M he reported earning in 2024. Much of this amassed wealth comes from cryptocurrency—about $1.4B of it—including revenue tied to the TRUMP memecoin and the crypto platform World Liberty Financial.

The filing also showed income from Trump's real estate holdings, golf clubs like Mar-a-Lago, licensing agreements, and other business ventures. However, it was the size of the cryptocurrency earnings that drew the attention of critics, who are namely arguing that a sitting president should not be profiting so heavily from businesses that could be influenced by his public office.

Across social media platforms, users expressed their outrage with the president's excessive wealth. "You can call this transparency all you want to and I am sure Trump supporters will say so, but transparency as they put it does not make it legal," one person wrote on X. "This is corruption on a level this country has never seen."

"This president has proven himself to be corrupted," another user agreed. "Total disregard for our democracy and the constitution along with the people who were dumb enough to vote for him. He’s vulgar and a grifter."

"How is anyone comfortable with this??" asked another person.

Author:

Freelance Writer

Julia DeKorte is a New York-based writer. A graduate of the Columbia Publishing Course, Julia covers celebrity and brand news for SheFinds, reviews toys and games for People of Play, and loves cooking for her family, walking her dogs, and running outside, preferably in view of the ocean. Contact Julia at julia@shefinds.com.

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