Donald Trump has spent years portraying himself as the hero who always comes out on top. But when one man cast doubt on the president’s political comeback, he may have forgotten one thing: Trump never sees himself as the loser. One minute, he’s defending Trump. The next, he’s saying som ething that could put him on the president’s bad side. Bill Maher reveals how his superhero comparison failed to sway Trump, exposing the president’s refusal to accept defeat before their latest White House dinner reignited their bitter feud. (Photo by Nicholas Hunt/Getty Images) Trump’s on-again, off-again friendship with one comedian has included public praise, and some nasty exchanges that suggest neither man is particularly good at letting things go. Everything was good until their most recent private White House dinner. ‘Don’t Call Anymore!’: Bill Maher Strikes Trump’s Most Painful Sore Spot, Triggering an Unprecedented, Record-Breaking 1,323-Word Meltdown Trump’s White House Dinner Spirals Into a Four-Hour Showdown as Guest Reveals the President Refused to Back Down and ‘Wouldn’t Let Us Leave’ Bill Maher is pulling back the curtain on his conversations with Trump, including a Hollywood comparison that failed to land well at their latest dinner. And judging by Trump’s explosive reaction, whatever goodwill the two had built didn’t last very long. During a recent episode of his “Club Random” podcast with “Breaking Bad” actor Dean Norris, Maher recalled trying to convince Trump that losing the 2020 presidential election actually worked in his favor. “I tried to convince him the first time I had dinner with him that actually losing the in-between election was the best thing that ever happened,” Maher explained. “Because it’s like in a superhero movie, or really any movie, you know, there’s three reels,” he continued. “The hero has to fall in the second reel so that he can rise again.” For someone who once made a cameo in “Home Alone 2: Lost in New York,” Trump apparently wasn’t buying Maher’s Hollywood lesson. “Everybody else in the world seems to understand the concept that it’s OK to lose,” Maher said. “It’s how you come back from losing.” “That’s not Trump,” he added. Maher broke down part of the conversation from the White House dinner on Oct. 15. “He said this a few nights ago: ‘I won the popular vote three times.’ I said, ‘You won it once,'” he recalled about the dinner, which was also attended by ESPN personality Stephen A. Smith and Trump supporter Kid Rock. Maher claimed Trump didn’t get angry when corrected. However, the president’s patience apparently expired once the comedian talked about the dinner on air. A week later, on Oct. 25, Trump unleashed a staggering 1,323-word Truth Social rant like he lost his best friend. He called Maher a “COMPLETE AND TOTAL LOSER” and a “major POTHEAD.” “Bill: Don’t call anymore,” Trump demanded, threatening to discourage Republicans from associating with the comedian. The explosion came after what Smith described as a four-hour White House marathon. “[Trump] wouldn’t let us leave,” Smith revealed, explaining that the president held them hostage as he insisted on addressing all of the disagreements he had with his friends and his occasional supporters. It’s the guests’ occasional shifts that have so many people up in arms. In particular, Maher’s political flip-flopping has become nearly as entertaining as his feud with Trump. The self-described liberal, who said in 2025 that he wasn’t a Democrat, regularly blasts the party over what he calls woke extremism while praising some of Trump’s policies. During his conversation with Norris, he even described the president as a “corrupt sheriff with Tourette syndrome.” “I’m very anti-woke extremism,” Maher admitted, suggesting Trump wasn’t entirely wrong about problems facing the country. That balancing act hasn’t impressed everyone. An MSN reader complained, “In some ways Maher comes across as Trump himself does. I know Maher is trying to be honest in his appraisal of Trump but it comes across as two-faced for some reason. Kinda like how Trump sounds when describing Maher.” “Bill, like Trump, loves getting attention. Both guys are past their prime. Getting older does not mean getting better for either of them,” another declared. Other readers questioned Maher’s sudden insider status: “You take a dinner with orange trumb, and want credit for letting us know what REALLY happened??? Get lost.” Someone else compared the entire spectacle to “Alice in Woderland’s Mad Hatter’s Tea Party.” The latest fallout adds another chapter to their feud, which dates back to 2013, when Trump sued Maher over a joke about his ancestry. Trump later withdrew the lawsuit. Despite their rocky history, Maher has defended both White House visits and praised Trump’s hospitality. But after spending seven hours together, the comedian offered a troubling assessment. “I think he’s honestly losing it,” Maher told Norris. “Or then gaining it. I don’t know.” For all their friendly dinners, Trump and Maher appear right back where they started. And this time, the president has made it clear that the comedian shouldn’t expect another invitation. Bill Maher Drops Bombshell About Private Trump Conversation That Exposed the President’s Biggest Sore Spot — Then Trump Exploded ...read more read less