Ex-colleagues say Keith Olbermann needs ‘serious help’ as career fades
Former ESPN and MSNBC host described by peers as increasingly embittered and isolated, with threats online and a diminished influence in media.
Keith Olbermann, the 66-year-old broadcaster once a fixture at ESPN and MSNBC, has become the focus of renewed scrutiny as colleagues describe him as embittered and increasingly isolated while his media influence has waned. The latest development centers on a string of inflammatory posts on social media, including threats toward CNN contributor Scott Jennings in the wake of Charlie Kirk’s death. Olbermann later apologized after Jennings shared the exchange with the FBI.
Former ESPN anchor Sage Steele told The Post she believes Olbermann needs serious help and described the worsening pattern of online rants as heartbreaking for those who knew him during the height of his career. “We thought for many years that he was losing it, and I say this honestly and out of concern for another human being,” Steele said. “Anyone who posts such hate as he often does and the language he uses, there’s something that’s not right.” Steele, who worked with Olbermann at ESPN, added that she remains worried about his mental health as his public persona grows more unpredictable.
Olbermann’s career arc runs through a pair of stints at ESPN and a lengthy run at MSNBC. He was fired from ESPN in 1997 but was later brought back; in 2015 the network chose not to renew his contract. He then spent time at MSNBC, where he remained a prominent voice until leaving in 2011 after clashes with management. A prior suspension in 2010 stemmed from donations to Democratic candidates, a move that violated the network’s ethics policy. These episodes are frequently cited by former colleagues when describing a pattern of volatile confrontations rather than a single misstep.
Beyond the cameras, Olbermann has cultivated another public-facing cause: dog rescue. He lives in New York City and maintains his childhood home in Westchester with his sister, according to public records. Friends and former colleagues say he rarely leaves the house unless someone can help with his several dogs, and he spends upwards of $1,000 a week to aid canine rescues. He has posted about finding homes for rescued dogs on X and works with Animal Control Services in the city. That quieter, philanthropic side contrasts with the volatility of his online persona, observers say, underscoring a fragmented public image.
The rift between Olbermann and some of his former colleagues extends into personal history. Steele recalled a 2021 interview in which Olbermann criticized her remarks about interviewing then-President Joe Biden for ESPN, though she indicated the comment reflected a broader pattern rather than a single grievance. In recent years, Olbermann has lashed out at former partners as well, including Fox broadcaster Laura Ingraham and former U.S. Senate candidate Kyrsten Sinema, as well as MSNBC anchor Katy Tur, whom he dated from 2006 to 2009. Tur, now a prominent journalist in her own right, described in 2022 how Olbermann had helped her early in her career but left an imprint of acrimony that persisted long after their relationship ended.
The Post and other outlets have chronicled Olbermann’s online behavior, including a 2022 incident in which he recounted boosting Tur’s career, then pivoting to aggressive personal commentary about her. He has also described relationships with other women in florid terms on air and on social media, comparing his past, often complicated, dating life to the pressures of public scrutiny. A review of those episodes by colleagues suggests a pattern in which professional admiration coexists with acrimonious personal expressions.
Observers note that Olbermann remains a controversial figure whose professional influence has declined while his personal notoriety has persisted. In recent months, he has used his platform to champion dog adoption and rescue efforts, a cause that some see as a sincere personal interest even as others view the broader behavior surrounding his career through a more critical lens. He did not respond to a request for comment from The Post for this story.
Images accompanying this profile show Olbermann during various phases of his public life and his canine advocacy.
As the current media environment continues to evolve, observers say Olbermann’s trajectory—once marked by outsized influence and confrontational style—offers a compact lens on the volatility that can accompany long-running careers in political and sports media. While his name remains a reminder of a certain era of cable news and countdown commentary, colleagues warn that the line between sharp critique and personal rancor has grown increasingly blurred. The question for many is whether Olbermann will seek a path that reconciles his public persona with the private concerns raised by former colleagues.
Further context about Olbermann’s personal life and career history remains a matter of public record and ongoing reporting. His team and the networks he has left have not issued comments for this piece, and the individuals cited here spoke on background to share impressions of a figure who helped shape a generation of sports and political punditry while simultaneously becoming a symbol of the tensions that can accompany public life.