The Trait That Won Scaramucci Over
Before their very public falling out, Anthony Scaramucci genuinely liked Donald Trump. And when asked what he appreciated most about the president during their friendship, his answer might surprise you: Trump's sense of humor.
In a December 2025 Q&A that Scaramucci shared earlier this month, the former White House communications director described Trump as "very charming" and entertaining in personal settings. Those qualities, he said, made spending time with Trump enjoyable, especially while traveling together.
"Trump has a sense of humor," Scaramucci explained, though he was quick to add that the president is also "very sensitive" to jokes aimed at himself. Scaramucci recalled how they would often tease Trump about this sensitivity, even while acknowledging his natural wit and charisma.
Of course, Scaramucci made it clear he was talking about Trump the person, not Trump the politician. His concerns about the president's policy decisions and what he characterized as expansive use of executive power remain front and center.
Musk Agrees: Trump Is Naturally Funny
Scaramucci's assessment lines up perfectly with comments from Tesla Inc. (TSLA) CEO Elon Musk, who runs SpaceX and xAI in addition to his electric vehicle empire. Musk has described Trump as "the funniest person he knows."
Speaking on Katie Miller's podcast, Musk said Trump's humor is instinctive and effortless. He pointed to a specific moment during a White House meeting involving New York City Mayor-elect Zohran Mamdani as proof of Trump's comedic timing.
A reporter asked Mamdani whether he still believed Trump was a fascist. Before Mamdani could answer, Trump jumped in with a quip, saying it was "easier" to just say yes. Classic Trump, according to Musk.
From 11 Days in the White House to Crypto Billionaire
Scaramucci's relationship with Trump is, to put it mildly, complicated. Nicknamed "The Mooch," he served just 11 days as White House communications director in 2017 before being fired. The tenure was so spectacularly brief that it inspired the slang term "a Scaramucci" to describe a short period of time.
But Scaramucci has moved on quite successfully. He founded SkyBridge Capital, which managed $2.6 billion in assets by the end of 2024 and has made significant bets on cryptocurrency. A Fortune report from July 2025 estimated his net worth between $150 million and $200 million, with more than half of that invested in Bitcoin (BTC) and a substantial position in Solana (SOL).
Despite everything that went down between them, Scaramucci has given Trump credit where he thinks it's due. He called Trump's return to the White House earlier this year "the greatest comeback in political history." High praise from someone who knows firsthand how quickly things can change in Trump's orbit.
So there you have it: two very different people, from very different worlds, both pointing to the same quality in Trump. Maybe there's something to this humor thing after all.