A fiery media feud exploded into public view this weekend after former MSNBC host Keith Olbermann harshly criticized HBO’s Bill Maher following Maher’s controversial meeting with President Donald Trump. Olbermann unleashed a fierce attack on Maher via social media, accusing the “Real Time” host of compromising his principles for personal gain.
The controversy erupted when Maher openly described his recent White House encounter with Trump as unexpectedly positive. On Friday’s episode of his HBO show, Maher surprised audiences by calling the former president “gracious and measured,” insisting that Trump displayed none of the behavior Maher previously criticized.
“Everything I’ve ever disliked about Trump was, I swear to God, absent—at least on this night with this guy,” Maher stated candidly. The host acknowledged that his remarks would anger many liberals, humorously noting, “millions of liberal sphincters just tightened.”
Keith Olbermann, known for his blunt style and outspoken liberal views, immediately fired back with blistering accusations on X (formerly Twitter). “Don’t overanalyze Maher prostituting himself to Trump,” Olbermann wrote bitterly. “Maher works for the same fascists at Warner who took over and corrupted CNN.”
Not stopping there, Olbermann went on to describe Maher as a “shameless opportunist,” claiming he had been devoid of genuine principles since their first acquaintance in 1978. “He was a shameless opportunist then, and he remains one now,” Olbermann continued furiously. “This is purely about him preserving his HBO show.”
This isn’t the first time Olbermann has publicly clashed with Maher. In 2023, Olbermann viciously criticized Maher for deciding to resume airing “Real Time” during a Hollywood writers’ strike, famously labeling Maher as a “selfish and unfunny scumbag” at the time.
“Without writers, his new weekly scab edition of ‘Real Time’ will last about 83 seconds,” Olbermann sneered previously. “I’ve known you since 1978—F— you, Bill.”
Maher has remained unapologetic and even defiant, insisting that dialogue with Trump and similar political opponents is critical. He called out critics who were angered simply because he met with Trump at all.
“What am I supposed to do, not talk to him?” Maher questioned during his show. “As opposed to what—writing the same editorial a million times? Making 25-hour speeches into the wind? Is that really all liberals have?”
Maher further emphasized that his encounter with Trump didn’t imply political alignment, stressing he had “not gone MAGA,” nor was he pressured to. Rather, he said the meeting provided an opportunity for open communication between two people frequently positioned at opposite ends of the political spectrum.
One of Maher’s notable revelations from the meeting was how he and Trump mutually expressed frustration toward critics who condemned their decision to engage. “We both said we’d heard from people who liked that we were meeting. And we both said we didn’t like people who didn’t want us to talk,” Maher recounted.
While Olbermann and some liberal critics interpreted Maher’s stance as betrayal or opportunism, others see it as a positive step toward bridging America’s deep political divides. The fierce backlash, however, underscores the explosive nature of current media landscapes, where any perceived compromise or civility toward political opponents quickly spirals into controversy.
As social media continues to buzz and fans take sides, one thing remains clear: the rift between Olbermann and Maher highlights the growing tension within liberal media circles over how best to handle political dialogue in an increasingly polarized America.
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