why the New Yorker cartoon cover goes too far (by not going far enough)

Look, this is actually more complicated than the media shows. First, Wolf Blitzer and Chris Matthews and their lot are not helping themselves by implying that most people are stupid and won't get that the cover is satirical. They're not wrong. They're just not helping the Democratic cause by making us look like the snobs that we damn well are and ought to be after the crap we've endured the last 8 years from good-old-boy non-snobs.
But Wolf and his lot are to be excused for their latent reactions because the cartoon actually isn't explicitly cartoonish enough. It's too, forgive the phrase, New Yorker. Too, "Hi, I'm ironic. Figure me out." Because the object of satirization, the jerk-offs who encourage Obama is a secret terrorist spy, is missing from the cartoon, as is the extra and essential step of taking the rumors one step farther. Missing those, the cartoon doesn't quite come off, and that's what the people who are talking about this are somehow not noticing. I'm not saying it's not a good drawing, or that it doesn't incorporate the rumors well, or that it's not smart. It's just incomplete, and, as such, is sufficiently ambiguous in which side it's agreeing with that people who should know better are freaking out publicly. Shouldn't happen. Remnick should see that. But he doesn't.