I was surprised to learn how limited his numbers are. From my outsider's perception, I thought he was a much bigger deal, and more influential. However, Enten may have missed a trick here. If Stewart is that popular with other media figures, that increases his influence, as they might be taking their cue from him what targets they should be aiming at. As with a musician's musician or a coach's coach, the usual numbers may not tell you everything.
Sportswriters, particularly of the ESPN variety, like to show that they are Real Journalists, and you do that by showing that you know the prevailing journalist opinion, not by rocking the boat very seriously. (Incidentally, this is rather sad when topics requiring real journalism spill over into the sports world, as they must. When the need for a variety of angles arises, the Lodge generally has a received wisdom.) It may be that sportswriters are the place to go to figure out what the approved narrative is going to be. They are drawn from a similar pool of college students that senses which way the wind is blowing. I have a recent example of a young writer from Grantland* clutching the breast over Stewart's impending retirement. I thought him rather narcissistic - to think of himself as "voiceless" after Bush's inauguration in 2001, what with half the Senate, a majority of the SCOTUS, and the major news outlets solidly in his corner is sadly comical - but I thought he represented a fair slice of the young and hip. Perhaps less so than I thought.
I usually found Stewart witty, even when I disagreed and thought him unfair. His vaudevillian delivery is wonderful. I've only seen clips, and that may not be a rep sample. Yet even when I agreed and thought him spot on, to the point that I would myself send clips around, I usually felt a little dirty and regretted it afterward. He's mean, and he doesn't always do his homework. He shoots quickly in an effort to be first-to-market with the joke. Humorous meanness is absolutely necessary in a society, and it is better to do it well, with occasional humility, than do it poorly. I do fear that others meaner but less intelligent will take his place.
*That's an ESPN sector of columnists, for those of you who don't follow sports.