I think this is what it is. He basically just makes educated guesses which is fine but he is billed as an insider.
He is an insider. He's also a writer and an analyst/pundit, so a big part of his job is supplying a stream of information for an audience that demands it. When he's got inside information that he can share, he shares it. When he doesn't he fills the gaps with speculation, just like everyone else. Unlike everyone else he's probably working with at least a little extra information.
It'd be one thing if people were annoyed that he passed his speculation off as inside information, but in general he's pretty clear about when he's doing what. I'm not sure what else you could ask for from him (or McKenzie, or anyone else that does this sort of thing).
Edit: This Pacioretty thing is a good example. It's speculation, but it's well-reasoned speculation. I can't imagine there isn't interest in Pacioretty and a lot of that interest is likely to be tangled up with his impending extension.