The only real young guys the Sox might have thought about locking up under Bloom are probably:
Whitlock (Did sign for $18.75M x 4)
Houck
Dalbec (after 2020 or 2021)
Duran (can't think of a time that looked right.)
Of course, players like Betts, Bogey, Devers, Beni and maybe ERod, Vaz and a few others early on probably would have been best locked up (or not) under the DD years. We had a chance with Bogey, it seems, and Devers, even now.
It's hard for GM to gauge the market spikes, and certainly some of the numbers thrown around on Bogey a few months ago, seem like bargains, now, but it's hard to know exactly what went down and what the offers actually were.
If the Sox offered $160M/6 or $180M/7 tops, but BorA$$ would not budge from $200M/8, it looks, now, like $200M/8 was a steal, and maybe it was or would have been, but for all we know, even if Bloom & Co. predicted the rising market for top end FAs, they still might not have agreed to $200M/8 and maybe wouldn't, right now, if they could.
In that case, blame a faulty evaluation system, assuming Bogey does not go on to earn that, but again by what metric do we end up saying he was worth $200M/8, $160M/6 or $280M/11?
If they would have paid $200M/8 and did not, thinking nobody would pay that, and Bogey would come back and settle for $190M/8 or $170M/7, then it was a clear mistake, and a much different type than above's example.
Maybe, when they thought he was worth $160M/6, BorA$$ wanted $180M/7, and if we then offered $175M/7 a few months later, BorA$$ then wanted $190M/7. Maybe the Sox final offer was $190M/8, but BorA$$ demanded $220/8. At no point did the Sox feel they would meet Bogey's demands and their "set value" never matched with BorA$$. An agent's demand does not always match with a player's true value and with BorA$$ is usually grossly more than the expected final contract ends up being. In this case, I think Bogey got more than even BorA$$ thought he'd get 12, 6 or even 1 month ago.