I don't know the guy, but it seems to me that he really felt burned after what LBJ did back in 2010. He'd been right by the guy through his high school days, became the best reporter for the ABJ and then the go to guy for the Cavs period. He kept saying he thought LBJ would come back, and that he didn't think LBJ would go on TV and hurt the city. And then, the Decision.
I think Windy the journalist felt a bit burned by Windy the fan. Seems to me he made a conscious decision to try to not be a homer moving forward, both because he didn't want it to hurt his journalism, and because he didn't want to be burned as a "fan" again.
So, he ended up being something of a negative Nancy when it came to talking about Cleveland. He didn't want to get anyone's hopes up, including his own, and he didn't want to be accused by other national media types of being a Cleveland partisan. I do think that he probably took that too far sometimes, but I also think some of us are bit hypersensitive about his criticisms/reservations precisely because we are fans.
Anyway, I'm glad he'll be back. He never seemed like an egotistical prick, and I think he tries to be honest. Usually, he's got good sources as well, and I expect that will improve now that LBJ is back in his hometown.
Bottom line is that with everything going to well, it just doesn't seem the right time to hold a grudge anymore.