I don't know all those answers, but I just think baseball is just different. Ever notice how little these guys move around compared to the NFL and NBA?
Different kind of comradery. Coaches always seem more tuned in with the players. Everybody always seems more tight knit. He's only four years removed from playing and definitely seems like "one of the guys".
So, if these are your dudes, and you keep making it to the playoffs, how could other pastures be green enough to pull you away? He's already among the top earners in the league.
I'd say it would have to be a few more years of heartbreak or discontent before he would move on.