Trump, the man Maher once said lies as he breathes, signs a list of 60 insults he’s hurled at the comedian over the years, chuckling as he hands it back. Maher, the self-proclaimed “old-school liberal,” walks away with a stack of MAGA hats and a confession: Trump, in private, is “gracious and measured.” The guy he met isn’t the unhinged caricature he’s been skewering on HBO’s Real Time for years. What the hell just happened? 

For anyone who has followed Maher’s career, this moment feels like a plot twist in a Franz Kafka novel. Maher, the 69-year-old provocateur, has been Trump’s most relentless critic among major comedians. Since Trump descended the golden escalator in 2015, Maher has wielded his platform to paint the former reality show star as a danger to the republic. He has called Trump a “whiny little bitch,” compared his supporters to North Korean loyalists, and warned that Trump would never leave office voluntarily. On Real Time, Maher has made Trump the butt of countless monologues, accusing him of everything from election theft to siding with Russian President Vladimir Putin. Just last month, Maher said he’d vote for “Biden’s head in a jar of blue liquid” over Trump. So when Maher announced on his April 11 show that he had dined with Trump at the White House and found him surprisingly human, jaws dropped. Liberals cried betrayal. Conservatives smirked. And the political world buzzed with questions: Is Maher going soft? Or is he on to something bigger?

A decade of daggers

To understand the seismic shock of Maher’s White House visit, you have to rewind through a decade of vitriol. Maher’s disdain for Trump predates the presidency. In 2011, he was already mocking Trump’s birtherism, calling it a racist dog whistle. In 2013, the feud got personal when Maher joked that Trump’s father was an orangutan, prompting a $5 million lawsuit from Trump (later dropped). When Trump ran in 2016, Maher didn’t hold back. “He’s a con man,” Maher said on Real Time, warning that Trump’s appeal was rooted in primal charisma, not policy. “He’s a reality star, not a leader.” As Trump won the GOP nomination, Maher’s critiques grew darker. He likened Trump’s rallies to Nuremberg, predicted he’d rig elections, and accused him of inciting violence. After Jan. 6, Maher doubled down, calling Trump a traitor who tried to “overthrow an American election.” No comedian — not Jon Stewart, not Stephen Colbert — has been as consistently, brutally critical of Trump as Maher. His HBO stage was a weekly anti-Trump sermon, blending humor with apocalyptic warnings.

Yet, even as Maher hammered Trump, he was carving out a parallel identity: the liberal who critiques his own side. Over the past five years, Maher has turned his fire on the “woke Left,” a term he uses to describe what he sees as progressive overreach. He has railed against cancel culture, calling it a “purity test” that stifles free speech. He has mocked diversity, equity, and inclusion initiatives as dogmatic overcorrections, arguing they prioritize ideology over merit. “DEI has gone too far,” he said on Real Time in 2024, citing examples such as corporate quotas and university speech codes. He has also taken aim at transgender issues, opposing biological men in women’s sports and questioning the Left’s embrace of gender ideology. “I’m not transphobic,” he has insisted, “but I’m not going to pretend biology isn’t real.” These stances have cost him fans — Maher admits the “woke people have left the building” — but they’ve earned him grudging respect from conservatives, who see him as a rare liberal willing to challenge progressive orthodoxy.   

This shift has made Maher a political oddity: a liberal who votes for Democrats but sounds increasingly like a Fox News guest. He has praised Trump’s decision to dismantle the Department of Education, called for tougher border security, supported Israel’s military actions in Gaza, and condemned calls to defund the police. He has also opened his show to right-wing figures, a move that has raised eyebrows. On April 11, he hosted Steve Bannon, Trump’s former strategist, who was fresh out of prison. The two sparred over Trump’s third-term ambitions — Bannon claimed Trump would run in 2028; Maher cited the 22nd Amendment — but the tone was civil, even chummy. Days later, Maher welcomed Charlie Kirk, the Turning Point USA founder, on his Club Random podcast. Kirk, a MAGA firebrand, praised Maher’s “moral courage” for resisting the “woke crazy train.” Maher, in turn, lamented the Democrats’ inability to connect with voters, saying their obsession with messaging misses the primal appeal of figures like Trump. “Democrats need an alpha,” he told Kirk. “Trump does it better than anybody.”

White House wager

So why did Maher, the Trump-slaying comedian, accept Kid Rock’s invitation to dine with the president? On Real Time, he framed it as a quest for civility. “There’s gotta be something better than hurling insults from 3,000 miles away,” he said, recounting how Kid Rock pitched the meeting as a chance to “bring people together.” Maher, who has long touted dialogue across political divides, saw it as a test of his principles. “I’m doing it because it was presented as a beginning to heal America,” he told NewsNation’s Chris Cuomo before the dinner. “I don’t think I can heal America, but I have credibility with Trump’s base because I’m honest about the woke train to crazy town.” 

The dinner itself, as Maher described it, was a revelation. Trump greeted him warmly, took the group on a tour of the White House, and showed off the Gettysburg Address in the Lincoln Bedroom. They discussed policy — Iran, Israel, and the border — and Maher was struck by Trump’s willingness to listen. “I never felt I had to walk on eggshells around him,” he said. Trump even laughed, a rarity in public. “As a comedian of 40 years, I know a fake laugh when I hear it,” Maher quipped. Most surprising was Trump’s self-awareness. When Maher brought up the 2020 election, Trump used the word “lost.” “I never thought I’d hear you say that,” Maher remarked. Trump didn’t flinch. For Maher, the contrast was stark: The private Trump was “not the guy who s***-tweeted nasty crap about me the night before.” 

Maher’s monologue sparked a firestorm. Liberals accused him of “normalizing” Trump. Washington Post columnist León Krauze compared Maher’s praise to journalists charmed by Fidel Castro or Josef Stalin, warning that private charisma doesn’t erase public harm. Democratic strategist James Carville called Maher “supremely naïve” for falling for Trump’s hospitality. On X, commentator Wajahat Ali fumed: “Congrats, @billmaher. You got played by Trump. Easy mark.” Conservatives, meanwhile, gloated. “Bill Maher says he was completely wrong about Trump,” Collin Rugg posted, citing Maher’s comments about how the Cornell-educated comedian felt more comfortable with Trump than with former Presidents Bill Clinton or Barack Obama. Kid Rock, on Fox & Friends, said Maher’s “mind was blown” by Trump’s charm. “Everyone walked away saying, ‘Wow, what a great guy,’” he boasted.

The saga took a darkly comic turn on April 21, when Larry David, Maher’s longtime friend and fellow comedian, published a scathing op-ed in the New York Times titled “My Dinner With Adolf.” In a questionable piece of Swiftian satire, David imagined dining with Hitler in 1939, marveling at his “pleasant” demeanor and “beautiful art” stolen from Jewish homes. The piece never named Maher, but it was a clear jab at him, mocking Maher’s openness to dialogue and his apparent softening toward the sitting president. David’s Hitler even laughs at a joke about his tan suit, a nod to Maher’s praise of Trump’s humor. “I’m so thankful I came,” David’s narrator tells Hitler, giving a Nazi salute before leaving. The subtext was brutal: Maher’s cozying up to Trump is as delusional as dining with a dictator.

Maher hasn’t yet responded directly, but his likely retort is predictable. “This is exactly why I went to see Trump,” he’ll probably say. “Because he’s not Hitler. The Left’s obsession with equating him to history’s worst monsters is why they’re losing touch with voters and why they continue to lose elections.” On his podcast with Kirk, Maher hinted at this, arguing that the Left’s refusal to engage with Trump as a human being fuels its political irrelevance. “They just don’t feel like he’s a real person,” he said. “That’s why Democrats are so unpopular.”

Maher’s White House gambit is arguably the most audacious move of his career, a Nixon-to-China moment for America’s most influential comedian-pundit. Like President Richard Nixon’s 1972 trip to Beijing, which shocked the world by bridging a Cold War divide, Maher’s dinner with Trump challenges the tribalism that defines modern politics. By sitting down with his longtime foe, Maher is betting that dialogue can pierce the echo chambers that dominate public discourse. He’s not endorsing Trump — Maher still calls his policies “terrible” and vows to keep criticizing him when criticism is warranted — but he’s rejecting the Left’s dogma that Trump is untouchable. “I didn’t give one inch on what I believe,” he insisted on Real Time. “But I told the truth about how he’s different in private.”

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The political implications of Maher’s move are profound. The Maher-Trump truce could signal a broader shift among centrists and independents, who are increasingly alienated by the Left’s moralizing and wokeism’s religion-like cultishness. Maher’s critiques of DEI and wokeness resonate with voters who feel suffocated by progressive orthodoxy but who aren’t quite ready to don MAGA hats. By engaging with figures like Bannon and Kirk, Maher is modeling a third way: a principled, old-fashioned liberalism that’s unafraid to question its own side or talk to the other. If Democrats heed his warning about their disconnect with voters, they might rethink their strategy. If not, Maher’s prediction — “They’re never going to win another election” — could prove prophetic.

Culturally, Maher’s move challenges the entertainment industry’s anti-Trump monoculture. Comedians like Stephen Colbert and Jimmy Kimmel have built empires on Trump-bashing, but Maher’s willingness to humanize him could inspire others to prioritize nuance over outrage. It’s a risky bet — Maher’s ratings may suffer if liberal fans abandon him — but it’s a bold stand for a comedian who has always prized truth over applause. His dinner with Trump isn’t about capitulation; it’s about confronting the caricature and finding the man beneath. Whether that man is a “gracious” everyman or a calculating showman, Maher’s journey to the White House proves one thing: In a polarized age, the real rebellion is conversation.  

Daniel Ross Goodman is a Washington Examiner contributing writer and the author, most recently, of Soloveitchik’s Children: Irving Greenberg, David Hartman, Jonathan Sacks, and the Future of Jewish Theology in America.