President Donald Trump brought together an unlikely trio at the White House Thursday: longtime supporter Kid Rock, liberal comedian Bill Maher and outspoken sports commentator Stephen A. Smith.
More than four hours later, Smith walked away surprised by how much time the president devoted to answering their questions.
“It was shocking. I certainly didn’t expect that amount of time,” Smith told CNN’s Laura Coates Friday night, according to The Hill.
“I give him all the credit in the world because he didn’t run from any questions. Anything we asked him, he kept coming back at us with the things that he had to say.”
The gathering brought sharply different political perspectives to the same table less than three weeks before the November midterm elections. Trump offered his own favorable review Friday, calling the dinner informative and praising his guests.
Tough Questions Over Dinner
Smith said he accepted the invitation to raise concerns about funding for historically Black colleges and universities. The discussion expanded to include the economy, the midterms and the Texas Senate race, The Hill reported.
He said he challenged Trump on public dissatisfaction with the economy and the president’s standing in the polls. Trump remained confident that conditions would improve and maintained that Republicans continued to support him.
Smith also criticized Republican Senate nominee Ken Paxton’s refusal to debate Democratic opponent James Talarico. According to Smith’s account, Trump acknowledged that he had a good point.
The exchange came despite recent public friction between Trump and the ESPN personality.
The New York Post reported that Trump attacked Smith’s intelligence in June after Smith criticized his attendance at a New York Knicks game. By Friday, the president was praising him to reporters.
Smith told Coates that he and Trump had known each other for years, but that Thursday marked their first face-to-face meeting in more than 15 years.
“This is the first time I’ve seen him face to face in over a decade and a half, and I saw it as an opportunity to make my case,” Smith said, according to The Hill.
Maher Returns After an Uneven Truce
For Maher, the dinner marked another chapter in a relationship that has swung between cordial private conversations and pointed public criticism.
Kid Rock helped arrange Maher’s first White House dinner with Trump in March 2025. Afterward, the HBO host described Trump as personable and receptive during their conversation, drawing criticism from some viewers who opposed the meeting.
That encounter did not end their disagreements. Maher continued criticizing the president on “Real Time,” and Trump complained in February that hosting him had been a waste of time, Variety reported.
Nevertheless, the two were willing to meet again.
Speaking Friday, Trump suggested their personal rapport was warmer than their public exchanges might indicate.
“Bill Maher — I will tell you what. He likes me a lot more than people understand, and I actually like him,” Trump said.
Kid Rock Finds Common Ground
Kid Rock has the longest-established political alliance with Trump among the three guests. The musician visited the White House during Trump’s first term and performed at the 2024 Republican National Convention.
His friendship with Maher also helped create a connection between the president and one of his persistent critics.
Discussing Thursday’s gathering on “Fox & Friends,” Kid Rock said the group disagreed on some issues but found common ground in opposing socialism and communism in government. He also described discussions about Black women’s unemployment and HBCU funding.
The evening extended beyond the dinner table. According to Smith, Trump also took the guests through parts of the White House, including the West Wing and Rose Garden.
Trump’s assessment afterward was straightforward: “It was a good dinner.”
