If someone had told you two years ago that ESPN wouldn’t be renewing Keith Olbermann’s contract at the end of his current deal, you would have probably assumed, based on precedent, that the reason would be yet another series of off-camera dustups between Olbermann and the powers that be—that those powers had decided that life is too short for more battles with the legendarily contentious Keith.

The final act of the Olbermann script had played out that way in essentially every other high-profile anchor job he’s had before: MSNBC (twice); Fox Sports Net; Current TV; and, of course, ESPN, in his original, star-making round with the cable sports giant, which ended in acrimony in 1997.

And yet how mistaken you would have been. ESPN management confirmed Wednesday that indeed they will not be renewing Olbermann’s current contract, but close observers know that Olbermann spent his past two years in this second go-round with the network with his gun atypically in its holster, despite numerous temptations, or at least opportunities, to fire off a few rounds. Not even ESPN executives dispute this. They went out of their way to make the parting look as amicable as imaginable.

So what did go wrong? In short, ESPN never got past foreplay with Olbermann. Yes, they brought him back, but they kept him out of the corporate campus in Bristol and in New York. Yes, they gave him his own show and platform, but they aired it on ESPN2—first as a movable feast, pushed all around the schedule by delays after live sporting events, and later at five P.M., when the only available viewers are the proverbial friends and relatives. For this Olbermann deal to have really made sense, ESPN would have had to go for the Full K.O.: Put him on SportsCenter, the flagship property he helped make a TV institution two decades ago, and let him do what very, very few have ever done so well.

Or at the very least, give him a show with a stable time slot and spread his distinctive voice throughout the ESPN digital ecosystem—including, yes, on SportsCenter.

When ESPN started back with Olbermann two years ago, there was skepticism about the 11 P.M. time slot on ESPN2 because that network airs so many live sporting events—from grand-slam tennis to a wide array of sometimes minor N.C.A.A. offerings that it must broadcast as part of larger and more significant N.C.A.A. deals. (Want college football? First find a place for women’s softball.) Olbermann was initially told that such delays might occur 20 to 25 percent of the time and would probably only last on average 15 minutes each. In the first six months of his return, his show was delayed more than 60 percent of the time, sometimes airing up to an hour late, or even more.

Interestingly enough, or shockingly enough, Olbermann took it all in stride. The old Keith would have walked off angrily, or at least threatened to, or might have gone to Defcon-1 during molten meetings with management. Not this time. Not this Olbermann.

After a while, even ESPN management had to acknowledge that the 11 P.M. slot was a disaster and asked Olbermann to move to 5 P.M. But being on in the afternoon, where he had no opportunity to comment on the night’s action or highlights, was like a root canal.

ESPN president John Skipper and others had talked about their desire and need to give new life and meaning to ESPN2 (ironically the network Olbermann helped launch in the early 90s) and told Olbermann that with him on board, they’d be able to sell advertising at higher rates and revitalize the brand. They promised they would heavily promote Olbermann’s show and then, in a press release announcing the time change, went even further: “We feel that strategically shifting the time of this show will not only provide access to a broader audience, but gives us greater flexibility for Keith to do cross-platform opportunities, including hosting key editions of SportsCenter surrounding major news or events throughout the year.”

Skipper himself told insiders that he was thinking about returning Olbermann to SportsCenter. And yet the idea somehow never got past the talking stage and the promised “hosting key editions” of S.C. never came to pass. Either Skipper changed his mind, or more likely, the thought set off an internal war between those who truly wanted to give Olbermann another chance at superstardom and those who’d do everything they could to prevent his moving to either Bristol or Los Angeles and reclaiming the chair that he once occupied so prominently.

Although Olbermann didn’t really want to move to five P.M. in the first place, he took one for the team, going so far as to be paraded about at the network’s annual upfront presentation to advertisers. But the time slot turned out to be a sinkhole. Yes, there was a major car sponsorship—rare for that slot—and yes, Olbermann was nominated for his second Emmy as studio host (he had been nominated the year before for best show), but the ratings were anemic and, apart from Olbermann’s attacks on N.F.L. commissioner Roger Goodell, there wasn’t much sizzle.

In recent weeks, rumor had it that ESPN executives were increasingly concerned about Olbermann’s commentaries and his strafing of Goodell, whose league has a lucrative partnership with the network to broadcast Monday Night Football through 2021. ESPN is quick to counter that Bob Ley, Hannah Storm, and other on-air personalities have been equally if not more critical of the commissioner (Ley just received a new multi-year extension on his contract). But even if they were irked at Olbermann’s Roger Rants, that still leaves open the better and more obvious opportunity: putting Olbermann back on highlight-fueled and (mostly) commentary-free SportsCenter. After all, the station’s marquee program has had its share of challenges the past several years—partly because technology has made it possible for viewers to create their own score-and-highlight shows on their cell phones, and also because very few latter-day S.C. anchors have broken through to become real stars. It’s been a departure from the show’s DNA of old, when personalities like Olbermann routinely jumped from behind its anchor desk into the mainstream.

Though it’s ending with a whimper and not the customary bang, Olbermann’s second-time-around at ESPN does leave a threefold legacy of sorts. Olbermann proved that after spending years away in politics, he still had both the acumen and enthusiasm for thriving in the world of sports. He also showed that he had successfully engineered a dramatic about-face in terms of his own comportment, not only refusing to engage in heated battles but also giving up one of his favorite indoor sports—hitting back at trolls on Twitter (O.K., save for one incident).

But the final takeaway overrides the first two; ESPN tethered, and thus arguably nullified, Olbermann by keeping him away from one of the most important vehicles the network has. Once they’d made it clear that they were unlikely ever to put Olbermann back on SportsCenter, the deal just wasn’t worth it anymore.

James Andrew Miller is the co-author of the best-selling oral histories, Those Guys Have All the Fun: Inside the World of ESPN, and Live from New York: The Complete, Uncensored History of Saturday Night Live as Told by Its Stars, Writers, and Guests. He tweets at @JimMiller.