Sixteen years ago, when Keith Olbermann was last on ESPN, he was already a little bit of an anachronism. The time of ESPN2, of skinny ties, of literary-wisenheimer voiceover highlights, of bemused, outsider intellectualism -- of Olbermann -- was already starting to devolve, as all things original eventually do, into something vanilla, rote and mechanical. Every anchor started to sound like someone trying to sound exactly like Olbermann, only safer. To shoehorn in a tortured music analogy, Olbermann was Nirvana, and everyone else was Bush. Eventually, Bush started selling more records, and all the music started to suck.

The ambitious, restless Olbermann clearly sensed this, and -- like many a comedian who decides he wants to do legit drama to prove his chops -- went into news, first at NBC, then back to sports for an ill-fated dalliance with Fox Sports Net, before finally finding his place and his voice at MSNBC. (Before that blew up, too, of course.) One of the reasons Olbermann never stays anywhere that long is because part of him plainly doesn't want to: Staying too long means getting comfortable, and getting comfortable means starting to conform, and starting to conform means becoming a little more like everyone else, and that is always the last thing Keith Olbermann wants.

This is to say: Olbermann works best as an insurgent, as someone standing outside the world he's covering rather than holding the center of it. (It's another reason MSNBC, along with Olbermann's obvious partisanship, eventually halted his anchoring of election night coverage, even though he was by far their most successful personality.) It feels more natural, more just, when Olbermann is telling truth to power rather than actually holding the power. Which is why so many segments of "Olbermann", his new, instantly entertaining show that debuted on ESPN2 last night, felt slightly off. The ESPN of today is not the ESPN that Olbermann left. They're the big dogs now, and whether Olbermann would want to admit it or not, thusly so is he.

When Olbermann was lobbing rhetorical bombs at President Bush from the MSNBC chair, well, this was a guy on a then-fledgling basic cable network screaming into the void at the leader of the free world. But last night, when Olbermann began his show with a shockingly long, 20-minute screed against New York Daily News Jets beat reporter Manish Mehta, it felt less like a justified takedown and more like institutional bullying. Olbermann wasn't necessarily wrong about Mehta's (and the New York media's in general) ridiculousness about Rex Ryan and Mark Sanchez, but to rain that much thunder on a beat guy? To have Jason Whitlock come in and talk about how "incapable" Mehta was? For 20 minutes of airtime on a signature ESPN station? It was using the world engine to squash an ant.

It might not seem this way to Olbermann, but all that ESPN money and freedom come with a price, as it does for all personalities at the mammoth network. You are the establishment. And even though Olbermann obviously doesn't want to be roped in with some of the channel's more unsavory characters -- watching him openly recoil when Mark Cuban greeted him with "Welcome to the network of Skip Bayless!" was a highlight of the hour -- well, sorry man, but this is the world you've chosen and now inhabit. It was impossible not to watch the Mehta monologue -- criticizing the Daily News for inventing a story and then building reporting off their invented story -- and not to think of John Koblin's terrific detailing of ESPN doing that exact thing just last week, and in far more brutally efficient fashion.

Of course, Olbermann can't comment on that story, or any other ESPN story, and I bet this is going to be a serious problem for him in the coming months. His amused "I couldn't possibly comment" line in response to Cuban's Bayless jab worked last night, but it will only work once. Olbermann's at his best when he is in opposition to something, particularly something with power, but his network is the one that has all the power right now, and he can't say anything against it. It's like if his MSNBC show suddenly was transported to Fox News. Here, Keith, keep doing your thing about how right-wing media mutates and skews the news for the sake of self-sustainment … oh, and you can't talk about Fox News anymore. Every criticism Olbermann dished out last night applies to the network he works for, but he's not allowed to mention it, because they pay him. (Imagine the rant Olbermann would have had on the Frontline/ESPN fiasco were he on his MSNBC show.) Olbermann doesn't seem to know it yet, or care, but he works for his natural adversary.

Maybe Keith Olbermann will be able to abide by all those restrictions going forward. But if he can … I'm not sure he's really Keith Olbermann anymore.

Other observations from "Olbermann"'s first night:

  • Regardless of everything else, it is an undeniable joy watching Olbermann simply talk for an hour. (Or in this case, 63 minutes, because of course the first show ran long.) Olbermann's talent is mammoth, and just letting him go for an hour makes more compelling television than almost anything we've seen in sports in a while. Olbermann riffed like a man who has been away from a camera for way, way too long. It was riveting just to hear so many words said on a sports broadcast: I found myself almost out of breath by the end of the show, in a good way.
     
  • His eyes may have been bigger than his stomach, though: I'll confess the opening Jets monologue went so long, and was packed with so many asides and non-sequitors, that I kinda forgot what it was supposed to be about by the time it was over.
     
  • Whitlock - a fellow Bristol exile returning to the family - was a logical first guest, but I'll be honest: I don't have the foggiest idea of what he was talking about. As is typical with Whitlock, he starts out with a fascinating, provocative idea (how hypercapitalism forces every individual cog in its machine to ultimately eat itself, if I may Whitlockianly mix metaphors) and then proceeds to get lost along the way, eventually ending with some rambling confusion about the newspaper industry, or something. Whitlock always starts his monologues and his columns sounding like he's going to make sense, and he always finishes up somewhere far, far afield.
     
  • WORTH NOTING: Both of Olbermann's first two guests don't like me very much. Probably should mention that.
     
  • I suspect that "The Worst Person In The Sports World" segment isn't going to work as well here as it did on his MSNBC show (without "Sports"). First off, Olbermann's just not going to have as much freedom here as he did on that show. Second: It's a little more complicated than Olbermann makes it look sometimes. Last night, he chose Astros owner Jim Crane, because Forbes reported that the Astros were the most profitable team in baseball this year after the Astros slashed their payroll. There's more going on there than Olbermann made it look like, though. Crane and the Astros are actively trying to rebuild in a way that few teams ever do, and there's every reason to think the Astros will be spending money down the line. The Astros are not, say, the Marlins. Arguably, Olbermann could do a segment on the Marlins every night.
     
  • Even when he's doing his old schtick, Olbermann still makes me laugh extremely hard. The two best bits? A joke about the Rays players having issues with the sun - "which has being going on since the era of the dinosaurs" - and his frightened yelps every time a music video starring Bill Cowher showed the former coach in eyeliner.
     
  • Judging by a lot of Twitter reaction -- a perilous dependent clause on which to start a sentence, to be sure -- there is a certain segment of the ESPN audience that is just never going to be able to watch Olbermann without hating him for his political career. He might have been "burned out" by politics, but he is still an intensely polarizing figure for many sports fans. A certain right-wing viewer is going to see Olbermann the same way left-wing viewers saw Rush Limbaugh during his ill-fated cameo on the network a decade ago. This merits future attention.
  • The show's structure seems designed solely to amuse Olbermann. He only does highlights that were selected because he finds them funny. Olbermann's self-regard is overwhelming and, I'll confess, appealing. There's so much talent and skill on display here. It's already so different and refreshing. I'm just not sure, in this form, it can become what it should be. Not on this network. Without question, though: I'll be watching to find out.

Email me at leitch@sportsonearth.com, follow me @williamfleitch or just shout out your window real loud, I'll hear you. Point is, let's talk.