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Keith Olbermann in New York in October 2016. CreditSasha Maslov for The New York Times

Keith Olbermann doesn’t look much like a warrior. His gray hair is giving way to white, his midsection threatens the buttons of his sport coats and he walks gingerly, with a gnarly limp from an aging knee. When I visited him in late January, he was ill, hoarse and racked with fits of coughing. But when he hobbles into his studio and sits, a table shields his less flattering proportions, accentuating broad shoulders and an icy blue gaze. And when he starts to speak — confidently, quickly, alternately gesticulating or pretending to read from a stack of papers — he looks more like the man he used to be: the broadcaster who helped not only revolutionize sports news, but also invent a new mode of liberal cable-news political commentary.

His current show — a series of web shorts titled “The Resistance” — is not on cable and was not supposed to exist at all. It began last September as “The Closer”: six- or seven-minute monologues, written and performed by Olbermann and posted twice a week, on YouTube, the web and social media, by GQ magazine. It was expected to end after Election Day, but Trump’s win changed that. On Nov. 16, one week after Hillary Clinton conceded the election, Olbermann sat down at the desk of a spartan set constructed mostly of blankets, inside a cavernous photo studio on the 24th floor of 1 World Trade Center, and declared war on Donald Trump. “Since no Democratic or liberal politician has yet stepped forward out of the morass of Politics Inc. to take on the responsibility of the resistance,” he said, “I, with complete awareness of the presumptuousness and arrogance of this statement, volunteer myself.”

In the weeks after Trump’s election, the humor and levity sprinkled throughout “The Closer” vanished as the show narrowed its focus to a single mission: to end Trump’s presidency and see him “on a boat headed to the Cayman Islands.” According to “The Resistance,” the United States has suffered a “bloodless coup” and is “no longer a democracy”; the president is a “Manchurian candidate” who is “mentally ill” and beholden to “Russian scum”; we are witnessing the steady reduction of “the chance that we will have any future elections”; and Olbermann, the show’s tireless hero, will not rest until this problem is solved. “Is There an Actual Tape of Trump’s Russia Collusion?” an episode title asked last month. “There may be two tapes,” Olbermann concluded, citing a blog post from Louise Mensch, the English founder of the news and opinion site Heat Street — a former member of Parliament whose belief in Trump-Russia collusion is so strong she has suggested everyone from Ferguson protesters to James Comey is under Russian control. The world Olbermann describes on “The Resistance” is different from and even more dystopian than anything I can recognize, and his efforts to chase down Trumpian conspiracies can strain credibility. It was hard not to wonder what he was trying to accomplish, and what he truly believed.

A dozen years ago, from behind a desk on MSNBC, Olbermann reached career highs railing against President George W. Bush, as well as the Republican Party, conservative media and rivals like Bill O’Reilly. Back then, less than a decade after the debut of Fox News, the political right had already created an enormously profitable and influential universe built on partisan news and, more centrally, white rage. Liberals were scrambling to figure out what a left-leaning response to it might look like. Only a few scattered voices (Jon Stewart’s “The Daily Show,” Michael Moore’s documentaries, Al Franken’s books) were breaking through, and some grand plans (like the Air America radio network) struggled to make an impact anything like their right-wing counterparts. It was Olbermann — the anchor whose five-year stint at ESPN’s “SportsCenter” helped bring a wry, freewheeling humor to sports news — who answered the question of what a fiery liberal television commentator might look like. After Bush’s re-election in 2004, Olbermann’s show, “Countdown,” began injecting commentary into its news reports, thrashing against the administration and right-wing media with a sense of righteous rage. Its ratings soared, and Olbermann kept up his pious lectures through Barack Obama’s 2008 election. “I think I helped open a door for criticism against Bush and particularly the politicizing of terror in 2005, 2006, 2007,” he told me.

These were the years during which Olbermann had a prime-time cable-news show, millions of loyal viewers and a salary to match. Things are obviously different now. During the last week of April, he appeared as a guest on the first episode of “The President Show,” a Comedy Central program hosted by a Trump impersonator. “Don’t you think,” the faux president asked, “there’s a love-hate relationship between the mainstream media and the Donald Trump administration in a way that’s actually enhanced my presidency?” Olbermann agreed: “Yes, I think 100 percent. You’re absolutely right. It’s a symbiotic relationship.” It was hard to know quite what to make of the interview — hard to tell how seriously the impersonator was taking Olbermann, and hard to tell how seriously to take Olbermann’s own self-mythologizing — but very easy to recall that “The Resistance” will lose its reason for being the instant Trump’s presidency ends.

Olbermann has a favorite historical figure, Cincinnatus, whose story he likes to tell. It goes like this: Lucius Quinctius Cincinnatus was a Roman consul and military leader until 460 B.C., at which point he retired to a modest farm and planned to work happily for the rest of his days. He plowed his fields in peace for two years. Then, one day, he was interrupted by visiting Roman senators, who told him he’d been named dictator — and that a Roman army was being besieged by plebeians on nearby Mount Algidus. Cincinnatus raised an army and marched it to Mount Algidus, defeating the plebeians in a day. Rome was in his debt; he had control of the military and full dictatorial powers. He could have ruled Rome for life, but he didn’t. This is the part Olbermann loves: not that Cincinnatus saved Rome, but that afterward, he simply returned to his farm.

Olbermann is far from the only person to enjoy this legend. George Washington has often been called the American Cincinnatus; he retired to Mount Vernon immediately following the Revolutionary War and stepped down as president after two terms. Cincinnatus’ legacy has also been invoked more recently: There’s an echo of it in the Trump family’s frequent argument that their patriarch doesn’t need to be president and is sacrificing a life of unworried luxury for the good of the country. At 58, Olbermann is about the same age Cincinnatus is thought to have been when those senators arrived. And of course, as he sees it, he’s leading the fight against an unprecedented evil that threatens to corrupt and corrode the American way of life. An old email address of Olbermann’s is even named after the Roman. “What’s your farm?” I asked him, on the show’s set.

“His dogs!” a producer volunteered. But Olbermann corrected her. “Sports.”

Before Trump was Olbermann’s nemesis, Trump was Olbermann’s landlord. In 2007, Olbermann bought a condo in Trump Palace on the Upper East Side for $4.2 million, and he says Trump checked in to make sure he liked the apartment. “I saw him there at least once,” Olbermann says. “And I got a fan letter from him once.”

Olbermann says they first crossed paths in 1984, when Olbermann was a young sportscaster and Trump was the loud new owner of the New Jersey Generals, a team in the United States Football League, which folded in 1986 after only three seasons. Two decades later, Trump joined Olbermann under NBC’s corporate umbrella, as the star of “The Apprentice,” which first aired in January 2004 — the year Bush was re-elected, and the year before “Countdown” became a beacon for millions of liberal fans. One of those fans, Olbermann says, was Trump, still in the days when he moved in left-leaning New York circles and donated mostly to Democratic campaigns. According to Olbermann, Trump would tell him stories about how liberal he was, encouraging him to keep attacking Bush and commending him for championing the rising career of Barack Obama. (The Trump White House declined to comment.) This, Olbermann told me, is why he thinks Trump is mentally unfit for office: He can’t reconcile the man he knew with the one who ran for president, and is unnerved by the difference. The Trump he knew, he claims, had “no bluster.” Accounts from others who have known Trump for decades say his personality has been entirely consistent — even if it makes him prone to professing different beliefs depending on the situation.

On “The Resistance,” Olbermann insists that Trump is genuinely mentally ill; in person, he says that his psychologist friends, despite never having treated the president, have remotely “diagnosed” Trump with any number of mental illnesses, up to and including psychopathy. The argument feels wishful and familiar, bringing to mind challenges to Obama’s birth or religion from fearful, frustrated or opportunistic voices on the right.

Another thing Olbermann might find difficult to reconcile is the reversal in the two men’s fortunes. Twelve years ago, Olbermann was a player in the American political scene, with “Countdown” helping solidify MSNBC as the chief cable-news destination for liberal commentary; Trump, meanwhile, was emerging from a corporate bankruptcy into a role as a reality-TV host. Then came 2011. That January, Olbermann left MSNBC three months after being suspended for donating to three Democrats’ campaigns. In March, Trump entered the political conversation by insinuating that President Obama might not be an American citizen. Now Trump is president, and Olbermann is not on television at all.

In the same way that Olbermann’s work alongside Dan Patrick on “SportsCenter” created a generation of highlights shows and sportscasters following their wry, geeky style, the work Olbermann did on MSNBC birthed its own replacements. He is quick to name the mainstays of the network’s current prime-time lineup — Rachel Maddow, Chris Hayes, Lawrence O’Donnell — as people who guest-hosted for him years ago. This is an important year for each of them. Liberals woke up on Nov. 9 under a cloud of dread that hasn’t dissipated in the months since, creating a crucial moment for left-leaning political commentators on TV. In April, MSNBC’s weekday prime-time viewership was larger than CNN’s — the third straight month the network placed second among the cable news’s big three, trailing Fox News. Maddow, MSNBC’s biggest star and the tentpole of its evening lineup, has the most-watched and fastest-growing prime-time show on cable news.

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Olbermann in 2000, then a Fox Sports broadcaster, with his autographed baseball card collection.CreditGilles Mingasson/Liaison, via Getty Images

But Olbermann, who pioneered the form, can’t get back on TV. “I always thought that just wanting to be on television would be eventually classified formally as a mental illness,” he told me. “I do not exclude myself from this. I like to think that I treat it and I survive with it, the way other people survive with real diseases.” It can’t help that he has garnered a reputation as a terror to work with — known for haranguing and rebelling against the executives who pay him, feuding with the talent around him, making underlings feel small. He famously made his co-anchor Suzy Kolber cry when he was briefly moved to ESPN2 to start the channel and its flagship program “SportsNight,” and later went to war with Current TV when he was fired from the network in 2012, one year into a five-year, $50 million contract. He returned to ESPN for two years in 2013; in an oral history of SportsCenter, his colleague Rece Davis said that when rumors first arose that Olbermann was coming back, one coordinating producer said, “I think it would be a good idea, but with one caveat. He first has to stand in the reception area, and everybody who wants to gets to come up and punch him in the stomach.”

Olbermann was valuable during the Bush years because although political outrages abounded, no one else on TV seemed all that outraged. When stolid Tom Brokaw was the prevailing type, Olbermann was angry and sanctimonious. Liberal political commentary has shifted in the years since. The most prominent liberal commentators now, like Maddow and Hayes, are more grounded and forensic, delving into policy without drifting away from its human impact. This mode positions them and their fans on the left as smart, sane and righteous people in an age when so many prominent figures on the right — from Sean Hannity and Rush Limbaugh to the president himself — profit mostly from being angry and loud. It also has a dramatic range that Olbermann, known mostly for fiery to-camera oratory, tends not to.

Olbermann told me he talked to MSNBC for over a year about rejoining the network, but they asked him for a show with no commentary; he didn’t see the point. (An MSNBC source familiar with the situation confirms that there were talks, but says they fell through for a variety of reasons.) Olbermann also told me he had negotiated with CNN: “There was an offer, then there wasn’t an offer, then there was an offer. And Trump didn’t like me, and apparently exerted influence on that.” (A CNN spokeswoman says there were brief preliminary conversations about Olbermann joining its HLN spinoff, not the flagship channel, and that they took place well over a year ago, without any involvement from Trump.)

In March 2016, Olbermann wrote a column for The Washington Post announcing that he was moving out of Trump Palace. Trump responded in an email to CNN Money the following month. “Keith is a failed broadcaster, and the people in the building couldn’t stand him,” he wrote. “He is just trying to use ‘Trump’ to get publicity and stay relevant. The prices of Trump apartments are today the highest they’ve been. When people find out he is leaving Trump Palace, prices will probably go up.” It was the last time Trump would publicly acknowledge him.

On a frigid Friday afternoon this winter, Olbermann invited me to join him for lunch at the Atlantic Grill, a tony restaurant near Central Park. He was just coming down with the illness I’d see the following week on set, and within minutes, he received a call from his doctor. While on the phone, he recited his date of birth, which is how I learned that the meal we were sharing was his birthday lunch. He ordered us what he said were the best oysters in the city, then told a story about how he first really tried oysters six or seven years ago, while dating a woman from Cape Cod who could, he claimed, dive them out of the ocean and open them with her teeth. Until then, he’d spent his whole life avoiding seafood. “My dad grew up basically where the Throgs Neck Bridge is,” in the Bronx, he told me, “and as he said: ‘We never had fish growing up.’ He said: ‘The only thing I ever saw coming out of the water was missing union organizers.’ ”

Back in 2010, Olbermann used a Major League Baseball blog he was running to take a shot at one of ESPN’s most celebrated personalities, Bill Simmons. “I am again left to marvel,” he wrote, “how somebody can rise to a fairly prominent media position with no discernible insight or talent, save for an apparent ability to mix up a vast bowl of word salad very quickly.” Simmons responded in a tweet: “KO, please know the feeling is mutual. You’re my worst case scenario for my career in 12 yrs: a pious, unlikable blowhard who lives alone.”

It was cruel because it was factual. Olbermann is a bachelor with no children. His loves of history and sports seem less like escapes than parts of his job. He seems to have lived for little else until four and a half years ago, when he adopted his first dog. He’d never owned one before. “I avoided it for many years through, like, 12 girlfriends,” he told me. “Then one time the girlfriend was young enough that the family dog was dying.” They went into a pet store and emerged with a Maltese. A year later, he adopted a second. “And after I got them, I was calling all my friends who had dogs and saying, ‘Why didn’t you tell me this is the meaning of life?’ ” Olbermann now spends two hours a day outside with his pets; before the election, when the idea of a Trump presidency still seemed unlikely, he shot an episode of “The Closer” in which he examined whether Trump had ever owned a dog. (He couldn’t find any evidence.) When he dies, he imagined, “my last thoughts would be about the dogs. My next-to-last thoughts will be a flashback to how much I enjoyed ‘SportsCenter.’ ” Then he corrected himself. “I think my last thoughts will be: I pushed back against bad things.”

He tracks his show’s traffic obsessively and appears to spend much of most days on Twitter, sharing links to episodes and directing antagonistic tweets at Trump. He emailed me several times after we met with the average number of page views “The Resistance” was earning, boasting that the number of views per episode was between three and four million — numbers that would rival Fox News’s prime-time audience and surpass those of MSNBC and CNN. The difficulty with this comparison is that Olbermann isn’t a television anchor anymore. His work is online, where a “view” consists of three seconds on Twitter or Facebook, and 30 on YouTube. Television is a commitment: You can’t watch 10 shows at one time, so your choice to tune in at 8 to watch Tucker Carlson is a choice against Chris Hayes or Anderson Cooper. Online, you can open dozens of tabs, click away and never come back.

“He’s still looking out the side of his eye at cable,” his GQ editor, Geoff Gagnon, told me. “That’s his world. For years he lived in a profession shaped by certain values, by certain viewership metrics, that judge success in a certain way.” Cincinnatus’ fight required him to leave his peaceful farm, but Olbermann is currently fighting to return to the place he feels most at home. “If CNN called tomorrow and said, ‘We resolved the thing from two years ago; do you want to do the 9 o’clock?’ I’d sign,” he admitted, “and then go, ‘By the way, what are you paying me?’ ”

On some episodes of “The Resistance,” Olbermann sounds prescient; more often, and more recently, he doesn’t sound much removed from the unfocused rage and wild speculation that so many, including Trump, directed at Obama’s presidency. When he says that Trump is growing crazier by the day, or that he’ll soon be revealed as Russia’s puppet and impeached, Olbermann is suggesting to liberals that there is an endpoint — that the right mole, whistle-blower or leak will end their nightmare. He’s offering hope. The professed aim of the show may be to end Trump’s presidency, but it has another purpose too: It is a world built by Olbermann that justifies his existence. If “Countdown” was a refuge for liberals in a time of crisis, then “The Resistance” is a refuge for Olbermann himself. A man with his success and self-regard almost has to believe he has a role to play in shaping American history, and within this show, he is Cincinnatus — wanted, needed and fighting for the very soul of America.

As we ate our oysters, an older couple got up from a nearby banquette and, on their way to the exit, approached Olbermann. “Excuse me,” the man said. “I do miss you. Just terrible.”

“Thank you,” Olbermann replied warmly. When the man apologized for interrupting, Olbermann cut him off. “No, please. Watch me online,” Olbermann said. “Go to GQ.com; I do commentaries three days a week.”

“You know, the news is just terrible,” the man said.

“It’s not the same without you,” his wife agreed.

“Thank you,” Olbermann said again. Then: “Find me online; I’m doing the commentaries online.”

“GQ.com?” the man asked.

“GQ.com.”

“Cable news,” the old man lamented. “There’s no news.” And then the couple turned away.

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