I mean, JT Realmuto is both their best player and the highest paid catcher in all of baseball. They also traded a ton get him, although he has been worth every penny. Not trying to discredit your point, but probably important to point out.
That being said, Hahn’s ability to supplement this roster via free agency has been disastrous. IMO, there are two reasons for this. First, was several big misses in free agency that resulted in dollars being allocated differently than originally planned. Second, was the absolute failure to develop cheap pre-arb talent to provide above replacement level production at certain spots.
Regarding the first point, everything probably changes if Jerry nuts up and signs Machado to the deal the Padres offered. Additionally, let’s not forgot that Hahn actually prioritized a Wheeler signing and made a higher offer than the Phillies, but lost out due to geographical considerations. Can’t blame Hahn for the miss there, but can blame him for panic signing Dallas Keuchel. Yes, he delivered in a COVID shortened 2020 season, but was basically useless 18 months into that deal and was never going to be a true TOR starter for us.
So instead of having a cornerstone 3B & SP to build around for ~$55M/year in payroll commitments, those funds went elsewhere. Grandal is currently the largest free agency acquisition in franchise history at 4/$73M. I was a huge fan of the signing and won’t rip it now, especially when we needed a LH bat and the alternative was overpaying for James McCann. The problem was that was our only true high impact move in free agency. Maybe you can argue the Hendriks signing being one given how elite he is, but at the end of the day he is a reliever and that limits his potential impact to some extent.
But that doesn’t explain where all the money went. Let’s lay this all out. The core pieces that Hahn acquired during the rebuild accounted for ~$50M in salary this year (Moncada, Anderson, Robert, Eloy, Vaughn, Giolito, Cease, Kopech, Lopez, & Bummer). Beyond Grandal, Keuchel, & Hendriks (who made a combined ~$49M this year), the other two expensive core pieces were Lynn ($18.5M) & Abreu ($14M). That’s ~$132M in total payroll for seven everyday positional guys, four starters, and three high leverage relievers. That gave Hahn ~$54M to finish offer the roster. And that’s where the second problem comes in.
Because Hahn failed to build a steady pipeline of talent during the rebuild years, the Sox didn’t have cheap options from within to fill their remaining holes. Hostetler’s focus early on in low ceiling college bats with little to no defensive utility (Collins, Burger, Sheets, etc) created a system that lacked athleticism. The Robert signing limited what Paddy could do in subsequent years, which hurt our up-the-middle depth (just starting to see the fruits of his labor here with Sosa & Popeye). Getz & staff could not develop the few fringe prospects we had like Rutherford, Adolfo, Basabe, & Gonzalez into legitimate major league options (although SF did with the latter). And our pitching depth in the upper minors became a complete joke. Despite all the investments that we made into relief prospects, we struggled to develop a critical mass of major league caliber bullpen arms. Quite frankly, the prospect cupboard was quickly empty after the first few waves and organizational depth became non-existent.
So coming full circle, where did that other ~$54M go? Hahn spent $11.5M on Pollock to solve “RF” for a year (despite not being a RF) because all our minor league options had failed and Colas & Cespedes weren’t ready yet. He spent a combined $9.5M on Leury & Harrison to fill 2B for a year and provide some up-the-middle depth that he thought the system couldn’t. Rick spent $18M on two high-leverage relievers and a shitty swingman because the farm literally had nothing to offer. For that same $39M, we could have Bryce Harper playing RF ($26M) right now with Eduardo Escobar at 2B ($10M). All it took was for Hahn’s staff to develop four pre-arb guys to fill out a major league bench and bullpen, but unfortunately that was too much to ask for after a multi-year rebuild
TLDR - So yes, Hahn’s ability to supplement this roster via free agency has been a complete & utter disaster, but beyond just the poor resource allocation is an organization wide incompetence that lead him to prioritize depth over impact talent in free agency. And it’s those core failings in draft strategy and player development that should prevent from ever being a major league GM again.