Callahan's problem is that he's now just a cranky old white guy that most people despise, not because he's conservative or because his opinion differs from others, but because he's culitvated a persona that villifies the other side no matter what it is. Soccer, politics, food if you don't think like he does he spews hatred at you.
As a result he's become the broadcasting villain that no one likes.
Now you take affable Don Orsillo who's doing what he loves, never made an enemy in this town, has 3 World Series Rings, and is getting heroes send off, not from the team BUT FROM THE FANS and he just doesn't get it because all Orsillo ever did was enter people's homes for 3-4 hours a night for 15 years and people just liked him. (Hell, my wife switched from being a Yankees fan to a Red Sox fan because she enjoyed Don and Jerry) Few like Gerry let alone have any genuine affection for him.
So it makes sense. The Red Sox and NESN can't shit on Don on the way out, no rumors of affairs or pain meds, and they've already taken a beating by the public, so what do they do? Call their old buddy Gerry Callahan who's as tone deaf as they are and whine that they don't understand why he's getting so much love.
It's scary how much it's like Mr. Potter and George Bailey.