Things change. I know I am not at the top of my profession as Counsell is, and the dollars I deal with are six, not seven figures, but I had a good job that I liked with a software company here in the Madison area. Worked there seven years, and at the end of the seventh year, I felt I had gone about as far as I could go with that company. The company agreed, by giving me a nominal raise despite good performance reviews. They said I was at the top of what they paid people in my role. At that point I started looking. Found a job with another company that doubled my income from day one. Does that mean I was never "one of them" at the old company? Of course not, but things change, people change, and opportunities present themselves. I doubt that any person at my old job thought less of me.
And I think I need to do some digging through archives to read what Counsell has said "time and time again" about Wisconsin, MIlwaukee, and managing the Brewers. Not doubting it, I just don't remember hearing it much. I would be curious to see how many times he said it unprompted, as opposed to being a question from a reporter. "Hey Craig, what does it mean to manage the team from your hometown?" It would be impossible to answer that except in one way.
Counsell is a Brewer, through and through. I believe he cares about the city, the team, and its people. The last nine years have shown that. If you begrudge him a chance to take advantage of what he perceives to be a better opportunity, then you are the one who doesn't care about him, not the other way around.