No doubt, it was a hot debate for years. Many assumed Bogey would have signed for a reasonable deal a year or two before reaching free agency or even earlier in 2022.
I do think he'd have signed for less than the Padres gave him, but I'm not so sure the $160M/6 deal many seemed to think he'd have taken would actually have been taken, except maybe way back when he signed the extension under DD, with the opt out.
I think the Sox felt Story was similar in value as Boey- better D but worse on O. They felt $140M was better that whatever Bogey would have taken. I'm not sure I buy all the shock and awe Bloom put forth, when Bogey signed with SD. I think he knew they were too far apart, all along in the process, and that is why he jumped at Story in March '22.
I was not against bringing Bogey back, at what I felt was market value, but clearly we all miscalculated what that 2023 value was. Maybe Bogey knew all along he'd get way more than what Boston was floating.
I will say, departing players almost always say the same things. It's hard to know everything that went down and the true feelings Bogey had. If he thought he was worth $240M/8 or even $200M/7, and we never got close to those offers, I don't bame him for bolting. While $200M/7 looks pretty good, right now, back then, it seemed like a lot, and I can understand not offering that, especially with Story in the system, already.
I guess the best time would have been before we signed Story, or way back when DD extended him. We should have paid him more and not had an opt-out.