In the Room: The Real Keith Olbermann Story

Good evening, I'm Dylan Byers.

Welcome back to In the Room, my biweekly private email on the intrigue and inside story behind what’s going on in the media industry. In tonight's email, the real story behind Keith Olbermann's attempts to reinstate himself at MSNBC—and Jeff Shell's empty promises.

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The Real Jeff Shell-Keith Olbermann Saga

Behind the scenes, Olbermann has been privately jonesing to rejoin MSNBC for years, reaching out directly to Jeff Shell repeatedly. The whole situation simply manifests how bizarre things have gotten at the soon-to-be former House of Maddow.

DYLAN BYERS

Back in December 2019, on the day the news broke that Jeff Shell was going to become the chief executive of NBCUniversal, he received an email from Keith Olbermann, the former MSNBC host who was then working, for the third time in his career, at ESPN. The two men had known each other since the late 1990s, when Shell was the president of Fox's cable networks and Olbermann was a Fox Sports anchor.

In Shell's ascension, Olbermann saw an opportunity to engineer a return to the halcyon days of the mid-to-late aughts, when, as host of Countdown, he was MSNBC's marquee primetime star and one of the most powerful figures in American political media—a pre-Maddow Maddow of the now largely forgotten post-Iraq, Bush years. So began nearly two years of emails, which I obtained today, in which Olbermann repeatedly urged the executive to reinstate him at MSNBC and Shell repeatedly led the former host to believe that he wanted to bring him back to the network—and that it would just take a matter of time.

Earlier this week, Lachlan Cartwright of The Daily Beast first reported that MSNBC recently considered bringing back Olbermann to replace Maddow. The story was irresistible on a number of levels. First, it seemed like the sort of too-good-to-be-true fantasy homecoming that does occasionally occur when television executives run out of other ratings-boosting ideas. Second, it potentially demonstrated the fecklessness of MSNBC’s current management team, which capitulated to paying Maddow more to do less, has ceded all of the morning to Joe Scarborough, and airs a slate of schizophrenic programming on a quotidian basis—centrist and insiderly in the A.M., newsy during dayside, and catering to the A.O.C.-wing of the Democratic party at night.

The report that MSNBC was turning to Olbermann as a Hail Mary pass, in lieu of any better option, was attractive and seemed to make sense. In truth, the whole situation was a lot more complicated.

“I’d Do It, If Asked”

Returning to MSNBC had been a white whale for Olbermann for some time. In 2014, three years after leaving the network, he had one-on-one talks with then-NBC News Chairwoman Pat Fili-Krushel about resuscitating Countdown, sources familiar with those talks told me. In 2016, he had been in extensive negotiations with then-MSNBC President Phil Griffin for a show that he would have co-hosted with the Republican pollster and TV personality Kristen Stolis Anderson, sources familiar with those talks said.

But MSNBC executives wanted Olbermann to move from New York to Los Angeles for the job—even though Anderson would be based in Washington. Olbermann wanted assurances of a long-term commitment before moving to L.A. MSNBC didn't provide that. The talks fell through.

Olbermann, who had never rediscovered the pop culture celebrity he achieved alongside Dan Patrick on SportsCenter, and amplified on MSNBC’s air, seemed hellbent on a third act, even if it was a more modest one. “I'm about to go back into politics (again),” Olbermann wrote to Shell in the December 2019 email. “Don't need my own show, though I'd do it if asked.”

Olbermann went on to explain that his latest turn at ESPN “has been fun and cathartic, but SportsCenter is doomed, and more importantly... our form of government is about to change to authoritarianism and I'm not going to let it do so without me doing as many loud commentaries as I can.” He continued: “If any of this appeals to you, LMK. If my name doesn't ring a bell, don't LMK ;-).”

Shell responded: “Keith! It's so great to hear from you...I miss you personally and on air! This whole thing tonight is a bit premature”—his appointment as NBCUniversal C.E.O. was not yet official—“but if it does happen lets talk. I hope you are well.”

Two months later, on February 25, 2020, Shell’s assistant reached out to Olbermann to set up a dinner between the two men in late April.

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“MSNBC Is Woefully Underperforming in Prime Time”

Two days later, on February 27, Olbermann sent Shell a lengthy, unsolicited email offering his thoughts on the challenges that MSNBC faced and the opportunities the network had to boost ratings and generate more revenue. Despite the astonishing success of Maddow—a talent that Olbermann helped bring to prominence a decade earlier—the ratings were lagging beyond her hour. Meanwhile, the network was making about $400 million a year, whereas CNN was bringing in more than $1 billion, sources familiar with the revenues for both networks told me. Shell told Olbermann he would welcome his observations.

In a roughly 5,000-word dissertation-style email, complete with attached appendices demonstrating his research, Olbermann laid out a detailed and acerbic diagnosis of the cable news landscape and MSNBC’s troubles. He noted, for instance, that while Maddow’s ratings in the coveted 25-to-54 year-old demo were up 81percent from 2010, ratings for Chris Hayes’ show at 8 p.m.—Olbermann’s former time slot—were only up 3 percent. “There’s only one conclusion to be drawn: MSNBC is woefully underperforming in prime time,” he wrote. “And, while it is hidden by the amount of money [The Rachel Maddow Show] makes for you, the current 8 p.m. hour is the cause.”

Olbermann’s solution? “I think it’s not going too far out on a limb to believe that a revived Countdown would, at a minimum, produce numbers now in the same 100:95 ratio to TRMS as it did in 2010. In that scenario, at 8 p.m., MSNBC would be averaging 487,000 in the demo instead of 278,000. Profit would grow by 75% in that hour.” After noting that Countdown would very likely exceed his own projections, Olbermann added: “In conclusion, to twist the marvelous line from Chinatown, your 8 p.m. show is dying of thirst during a flood.”

Later in the email, Olbermann said he wasn’t asking for the job because of money. “If you want to reboot Countdown, decide on whatever salary figure would not embarrass you if somebody who didn’t like me were to leak it, and then fill the rest of the deal with demo bonuses based on the calculations and promises I’ve made above,” he wrote. Instead, he said, he wanted his show back in order to fight back against President Trump and the nation’s turn toward authoritarianism. “I truly feel our democracy is at stake and you, almost alone, can make a decision that may actually do something about it.” Olbermann then added that earth itself was at stake in light of climate change, another issue he intended to cover aggressively on the show.

“In sum, I’m suggesting the following: I can make you somewhere north of $50 to $100 million more a year than you’re making now and you can make it by fighting back against two existential threats,” he wrote.

Shell responded 23 minutes later: “Love the email, looking forward to dinner. Just fyi, I’m only two months into my new job change here and I’m not making any changes at all at news or anywhere else for a while. So I’m happy to talk about the world conceptually and your email certainly gives us lots to talk about, but I won’t be able to talk about anything specific or make any offers. If you’re ok getting together on this basis lets do it. If not, I understand and lets set a meal in a few months when I could be in a position to discuss specifics….”

The following month, the coronavirus pandemic struck. Olbermann and Shell’s dinner meeting, which had been scheduled for April 28, was pushed. And pushed. And…

“I’d Like to Bury Them For You. And for Mankind.”

Over the course of the next two years, Olbermann would send several emails to Shell in which he’d express his eagerness to start talking seriously about a show, whether on MSNBC or on NBC’s streaming service, Peacock. None of those emails ever turned into serious discussions or detailed plans about a specific program. In a statement, an MSNBC spokesperson said, “There was never any serious consideration of Kieth Olbermann returning.”

At the same time, Shell, ever the corporate statesman, never did anything to unequivocally disabuse Olbermann of the notion that he wanted to bring him back to the network. Instead, Shell told Olbermann to be patient, that discussions could resume after the 2020 election, and so on—emails that left Olbermann with the impression, perhaps wistful, that Shell was open to making something happen.

In the The Daily Beast story this week, Cartwright reported that MSNBC had been in “lengthy discussions” with Olbermann to bring him back to the network and that he “almost” got the job, but Maddow squashed the deal. That report, and a subsequent one from Fox News’ Brian Flood, made it seem as though MSNBC had turned to Olbermann in desperation, for lack of any better option to replace Maddow. It is a convenient and appealing storyline, especially in light of all the challenges the network is facing with Maddow’s impending departure, the loss of Brian Williams (and now Craig Melvin), and, most importantly, the lack of a strong editorial leader with a bold, strategic vision.

In truth, however, the email exchanges between Olbermann and Shell tell a different story, one in which Olbermann made unsolicited appeals to Shell and was repeatedly encouraged to believe that Shell shared his desire to strike a deal and bring him back to the network. Many current and former NBCUniversal executives I spoke to for this story point out that if Shell wanted to bring Olbermann back to the network, he would have made it happen—just as he personally greenlit Maddow’s historic $30 million deal with her agent, Ari Emanuel.

They also said that Olbermann should have read between the lines of Shell’s vague promises for future discussions. After all, that’s corporate life. The C.E.O. gets to be the good guy; it’s always the V.P.s who end up with the messes. Whatever the case, for at least 20 months, Shell gave Olbermann every reason to believe that the door was still open for his possible return. But it’s not. From what I hear, Nicolle Wallace is still the frontrunner for Maddow’s slot. Jen Psaki, who is expected to sign with the network, will work her way into primetime over a longer timeline. Olbermann is the odd man out.

On the night of May 31, 2020, with their dinner date on hold due to the pandemic, Olbermann, at home and watching CNN, sent Shell another email: “Hope you’re well. Midtown is happily deserted. I am watching [Chris] Cuomo and [Don] Lemon turn this nightmare into shows about themselves. I’d like to bury them for you. And for mankind.” Shell responded the next day with a one-word email: “Patience….”

Two months later, Shell sent Olbermann an email: “Morning Keith. So given the timing, we’re not going to make any significant programming changes until the election (assuming it happens!). let’s stay in touch and then we can talk or even get together in November.”

Shell and Olbermann did not get together in November. On January 5, 2021, Olbermann sent Shell another email that began, “Congrats on a year! I wanted to check in with you to see where we are on things….” Shell responded: “Still working on it and thinking about it…will definitely reach out in the next few months when I’m back in nyc.”

By the fall of 2021, Shell had passed Olbermann’s entreaties on to Cesar Conde, the NBC News Group chairman. On October 8, Conde’s assistant reached out to Olbermann to set up breakfast for the two men one week later. Minutes later, the assistant sent another email: “Apologies Keith, I just notice [sic] Cesar has a tentative trip that week. Let me get back to you with other avails.” Olbermann and Conde did not end up meeting in person.

By that point, it was clear to Olbermann that nothing was going to happen. Nevertheless, he received the following email from Shell several weeks later, on October 26: “Keith, I value our friendship, value your contribution to MSNBC, and particularly value your contributions to our democracy and civil society in the face of scarier and scarier threats. I’m sorry that we haven’t figured out a way to get you here in some capacity… Cesar runs the business and I respect his judgment and decision making. But please don’t give up, I’ll speak to Cesar and see if we can find a different path.”

On Wednesday, Olbermann told me that he was disappointed with Shell and suggested that, despite his desire to bring him back to the network, he had caved to others at MSNBC who didn’t want him there.

“I’m very disappointed in Jeff Shell,” he told me, clearly hurt. “The Jeff Shell I knew had courage and wasn’t bullied by people who depended on him for a paycheck. I understand it’s a huge company, but he did involve himself in this and there was never anything but encouragement from him about bringing me back to the network. And this attempt to gaslight everybody is not only beneath a major communications company like NBC and its chairman, but it's not even been done very well. Especially when I have an endless supply of receipts.”

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