From a purely strategic perspective, Stewart disarmed the right’s inevitable accusation that he’s ‘just a shill for the administration’ on his first night.
This was especially important because lots of Republicans and independents tuned in to see his return. If he had just gone after the right and ignored the major news about the Hur report and the press conference, or tried to play it off as nothing to see, he would have lost all that audience, and then had no opportunity to win them over later.
And I can report from also reading the right, that there was a lot of, “Hey, Stewart was pretty fair” coming from them. And he was funny. They’ll keep watching, at least for now.
He bought himself a lot of running room to go after Trump while the people who need to hear it are still listening. And if he needs to go after Biden a bit when deserved to keep those people, well… his Democratic audience is never voting for Trump anyway.
TV has way too many people on both sides acting as mouthpieces for their party and preaching to the choir. No one’s talking to the other side any more. If Stewart can lower the heat while also laying more damage on Trump than the Democrat, that’s kind of a win-win except for the fringes on both sides who just want to tear things down.