Michelle Obama and Jon Stewart Slam Trump's White House 'Perversion of Leadership' as Comic Calls Presidency 'Surreal'
Michelle Obama and Jon Stewart dissed the Trump family's financial ties.
Aug. 28 2026, Published 3:01 p.m. ET
Michelle Obama and Jon Stewart reflected on the Trump presidency and snarked over President Donald Trump's controversial leadership style.
The late-night TV personality spoke with the former first lady on her podcast, IMO, which she hosts alongside Craig Robinson. During their conversation, Stewart slammed the takeover of the Trump administration, RadarOnline.com has learned.
Michelle Obama and Jon Stewart Diss Trump's Leadership
Michelle Obama, Craig Robinson, and Jon Stewart sat down for a podcast episode.
Stewart called it a "surreal experience" for the Obama family, who worked to build a legacy in the longstanding institution. Now, he claimed, it was "corrupted" by the Trumps during two nonconsecutive terms.
"To have this perversion of leadership, I imagine, is especially difficult to digest," he said. "There’s a surreal quality to it."
Obama Family 'Left Money on the Table'
The Obama family, unlike the Trumps, didn't cash in on crypto while in office.
Obama and Stewart continued to reflect on some of the unusual, flashy moves from Trump, including those of his first lady, Melania. They famously launched a controversial cryptocurrency under her name as a meme.
"Although I have to say, you guys left money on the table," he said.
Stewart suggested the Obamas had an opportunity to do a "pump and dump" on the crypto market, which may have resulted in massive financial gains.
Obama also went on to throw shade at Donald and Melania dabbling in reality content. The couple released a documentary, Melania, which showed the current first lady's perspective behind-the-scenes leading up to his inauguration.
"We could have had a Netflix deal a decade ago," Obama scoffed.
Trump Family Accused of 'Corruption'
Donald Trump Jr. and Eric Trump invest heavily in weaponry and drones.
Stewart added, "You could have had a weapons company. You could've sold missiles to yourself. Don and Eric have a drone company. I don't even know what to say."
While Donald Trump Jr. and Eric Trump, who lost millions of his dad's money, do not own a weapons company, the pair are major investors in the industry. They financially back technology firms such as Powerus and Unusual Machines.
Stewart also took a deeper dig at the Trump family.
"You know, it's the level of corruption that is, in some ways, maybe it's doing a favor by making this, the current power structure and dynamic of this country untenable because of how explicitly corrupt," Stewart said.
Donald Trump's Net Worth Blooms
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Trump was accused of misrepresenting his wealth.
Forbes estimated Donald Trump's net worth increased by $4.1billion since taking office for his second term in January 2025. He's considered the most "lucrative" president, meaning he increased his net worth more than any of his predecessors during his time in office.
While most of his wealth is wrapped up in real estate, the additional assets are largely due to taking advantage of the cryptocurrency market.
Trump was previously accused of misrepresenting his own net worth substantially in an effort to bolster his credibility among the public. A New York judge ordered Trump to pay $454 million in response, but the fine was overturned by an appeals court in 2025.
