Is Montgomery really that guy?
He’s 30, and he was good in the AL East (3.94 ERA / 3.90 FIP). But to me that depends on the deal. He’s going to be an overpay on the trade market as the #1 name on every trade candidate list, and he might be reluctant to extend.
I could see it happening, but I could also see it not working out per your plan. He’s not a bad choice, but I’m hoping the Sox aren’t relying on extensions that haven’t been negotiated yet…