I see what you’re describing as somewhat akin to pandering. Grynbaum may have an opinion, & you may be able to figure out what it is, but if he’s doing the job well, don’t bet on the latter being right. That’s not a compliment, because the reason isn’t some loyalty to journalistic objectivity, but rather, the skill of making each audience think you’re talking to them. Give everyone — or at least, a wider cross-section of people — something to latch-on to.
I don’t know Maddow’s work well, have just seen a dozen or so of her spiels, but I get the sense she’s more focused on ‘authenticity’ as her brand. She wants people to know where she stands. That’s marketing, too, but it’s qualitatively different from what I see Grynwald doing, and what seems to me to have become more or less the standard: Be ambigious about what you’re trying to do. If you’re joking, be subtle enough that someone can plausibly take it seriously; if you’re serious, be sly enough that someone can plausibly construe it as a joke (or you can semi-plausibly make the case that they should).