Was Bill Maher Sucking Up to Trump and Bannon, or Just Breaking Bread?

Love or hate Donald Trump, he is perpetually at the center of the conversation right now, as he has been since he launched his run for president a decade ago. And in an attention-based media environment, the quickest path to achieving that goal, for better and ill, is to position oneself within a Trump-filtered lens.

Bill Maher thus joined the parade of unlikely characters to break bread with the president, having sharply criticized him and even been sued by him in 2013. The maneuver prompted the usual discussion about whether Maher — who also hosted right-wing operative Steve Bannon on last week’s installment of his HBO show — was normalizing deviancy, an understandably lament only if you haven’t been following Maher’s trajectory over the last many years.

Maher’s dinner with Trump, and discussion about it Friday, will surely alienate more of those people who had already begun drifting away from him. But he was trending throughout the weekend, his show has already been picked up through 2026, and angering people he sees as scolds is something Maher has long delighted in doing.

So for those keeping score, win-win, and maybe a small loss.

A little perspective is particularly helpful here — not just in Maher’s case, but more broadly. After all, the comedian isn’t the only high-profile figure to have made the pilgrimage to meet Trump since his reelection, following tech CEOs and MSNBC hosts Joe Scarborough and Mika Brzezinski and others, many of whom have alienated core constituencies in the process.

What makes Maher a little different is that he’s been cozying up to figures designed to elicit such outrage for a long time, even before his stint hosting his show from his mansion during Covid, a period that clearly fueled his desire to poke those on the political left in the eye.

In 2022, Maher proclaimed Covid “over,” said he didn’t want to be vaccinated but “took one for the team,” criticized public-health officials and declared he wouldn’t be getting any more booster shots. It was hardly the first time he provided billboard material for Trump supporters and conservatives who, wrongly pegging Maher as a liberal, reveled in wielding the “See, even Bill Maher agrees with us” line of attack.

Back in 2017, Maher was roundly criticized for hosting Milo Yiannopoulos, the right-wing media figure whose act turned out to be too toxic for even some of his conservative allies. In 2023, Maher was accused by some critics of “slobbering” over Elon Musk, during an interview in which the mogul railed against the “woke mind virus.”

In explaining his latest iconoclastic act, Maher employed what has become an increasingly familiar defense of his dinner with Trump, saying it’s better to be talking than not, even to those with whom one disagrees. California Gov. Gavin Newsom, who admittedly is playing a somewhat different game, sounded a similar note regarding his banter with Bannon and Trump loyalist Charlie Kirk on his podcast. Michigan’s Gretchen Whitmer, another Democratic governor with likely presidential aspirations, was also recently photographed, awkwardly, in the Oval Office.

That “better to talk” argument rings hollow for many. In Maher’s case, it’s not like comedians have ever needed to personally know the people they ridicule, but it’s as good an excuse as any to justify a transparent desire to thrust himself into the spotlight, even if that means potentially being used by Trump as a “prop” to do it, as one of his guests suggested. (Trump’s need to win over high-profile critics like Maher is another matter, one perhaps best left to biographers and psychologists.)

Nevertheless, Maher was characteristically defiant about the Trump meeting, saying on his show of the Kid Rock-brokered dinner, “You can hate me for it,” while noting that if his upbeat appraisal of the evening wasn’t enough “Trump hate” to mollify those upset by it, “I don’t give a f—k.”

Maher’s lengthy explanation actually undermines that last part, but he sounded genuine otherwise. As has happened time and again, the real choice now belongs to the audience.

Those who have watched Maher through the years — and haven’t yet been put off by his commitment to being a provocateur above all else — can decide whether they want to continue to make him part of their media diets. Trump supporters might briefly view him more favorably, only to find that a lot of what he says, like a high-fiber meal, doesn’t really agree with them.

What seems clear, though, is Maher isn’t the first and won’t be the last personality to irk many one-time fans by appearing to suck up to those which they find indefensible, then try to hide behind the shield of “Hey, we’re all Americans here, I’m just having a conversation and listening.”

It’s worth noting that whichever way the pendulum swings, Maher and those who occupy similar perches will ultimately be just fine. In Maher’s case, he just might be a little lonelier in terms of the guests he books, on his stand-up tours and when he retreats to that big house, the one where he openly stewed about not being able to conduct his show in person with a hooting and hollering audience.

The bottom line is leveraging Trump in pursuit of attention pays off in the short term, which has made the bargain attractive enough to entice plenty of unlikely characters into doing so, even at the risk of damaging their personal brands in the process.

As noted, Maher, like his elite media peers, enjoys a degree of insulation from blowback, but he still might want to consider the cost of his trending weekend the next time he stares down his audience for failing to laugh at a joke. Because for many, watching him and others self-servingly employ the “It’s better to talk” defense, and grasping what it says about the current media and political landscape, is more depressing than funny.

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