Keith Olbermann drags ‘opportunist’ Bill Maher for sucking up to Donald Trump for one desperate reason

Well, well, well… looks like Bill Maher has finally found a use for those knee pads he keeps under his “Real Time” desk.

After years of supposedly being a liberal voice of reason, Maher’s sudden transformation into Trump’s newest dining companion has former colleague Keith Olbermann spilling the tea on what might be the least surprising character revelation since we learned politicians sometimes lie. Turns out the man who built a career on smug intellectual superiority is — shocker! — just another showbiz opportunist willing to break bread with fascism if it keeps his Nielsen ratings healthy.

The drama erupted following Maher’s recent White House dinner with President Trump, an encounter arranged by that paragon of political sophistication, Kid Rock. Olbermann, never one to mince words or miss an opportunity to verbally eviscerate someone, took to social media platform X to dismantle his former friend’s character with surgical precision. “I’ve known Bill since 1978,” Olbermann declared, essentially dropping a nearly five-decade receipt on Maher’s desk. “He was a shameless opportunist with no real principles then and he remains so.”

BTW don’t overanalyze Maher prostituting himself to Trump

Maher works for the same fascists at Warner who took over and corrupted CNN

I’ve known Bill since 1978. He was a shameless opportunist with no real principles then and he remains so

This is so he can keep his HBO show

— Keith Olbermann (@KeithOlbermann) April 12, 2025

The dinner itself came after Maher had spent years positioning himself as a Trump critic, including a recent segment mockingly titled “Trump Devotion Syndrome.” Yet somehow, after breaking bread with the man he once suggested should be impeached, Maher emerged with a bizarrely softened stance, describing Trump as “gracious and measured” and suggesting that the “crazy person” we see on TV is just an act. Forgive me while I search for the world’s tiniest violin to accompany this revelation.

Olbermann wasn’t buying any of it, suggesting that Maher’s sudden change of heart had less to do with genuine enlightenment and more to do with corporate survival instincts. “BTW don’t overanalyze Maher prostituting himself to Trump,” Olbermann wrote with his trademark subtlety. “Maher works for the same fascists at Warner who took over and corrupted CNN.” Translation: Bill’s just trying to keep his HBO gig as Warner Bros. Discovery continues its rightward drift under new management.

What makes Olbermann’s takedown particularly devastating is the personal history behind it. When you’ve known someone for 47 years — through disco, through Reagan, through the invention of the internet — and your conclusion is “yeah, this tracks,” it carries a certain weight. Maher, for his part, has attempted to frame his Trump dinner as some sort of noble diplomatic mission. “There’s gotta be something better than hurling insults from 3,000 miles away,” he explained on his show. He even claimed Trump made him “feel comfortable” and that he “never felt I had to walk on eggshells around him.”

The timing of Maher’s Trump pivot is particularly interesting given the media landscape. As streaming services consolidate and traditional TV continues its death spiral, keeping a long-running HBO show alive requires either consistent excellence or a willingness to bend with the political winds. And based on Olbermann’s assessment, Maher has always been more weathervane than lightning rod.