It'd be an interesting conversation if he was 3 years younger. Unfortunately, this contract will only include 1-2 prime Bregman seasons before he regresses.
We've already heard that there is an internal conflict over Bregman between Breslow and Cora/Sam. My guess is that Breslow would rather use the $ to be spent on Bregman on pitching. I agree. Sox still have two MIF guys on the cusp of helping out. I don't know why they'd anchor themselves to more aging players the way they did with Story and Masa.