I am getting tired of the Chaim bashing, here and on WEEI, to be honest. Everyone is free to have their own opinion, and I'm not necessarily even saying that I'm right. But it seems to me that this is what's been happening.
1. The Sox won the WS with Dombrowski going all-in in 2018. It was amazing. Best year in Sox history, by a mile. Legendary team, ultimate outcome. Perfect. Then he re-signed Eovaldi and extended Sale, putting the Sox into a bit of a financial bind.
2. The Sox tank badly in 2019 and Dombrowski got canned. In comes Chaim. The farm system had been gutted in order to win the WS. Fine, I approve. But moving forward, the team needed a lot more ammo. 2018 was now gone and it was time to move to the next Sox championship team. They still had lots of good pieces but there were problems. One issue was Mookie's pending free agent status, which has been talked about ad nauseam here. I won't re-litigate it other than to say that the Sox believed they couldn't sign him for anything less than full market value. Nobody could foresee Covid and its impact on baseball and on Mookie's situation, so the Sox, not wanting to be hamstrung, traded him. Booooo. Nobody liked that but some people understood it. Tough for Chaim, to have been the one to pull the trigger on that.
3. 2020 is a disaster, thanks to Covid. Adding to it is that LA wins the WS with Mookie playing great. Ugh for Sox' fans. But Chaim begins the process of revamping the team. A HUGE part of that is rebuilding the decimated farm system. And that work begins in earnest. 2020 is a terrible season but the process has begun.
4. A ton of moves later, and the Sox are in 2021 and doing pretty well. Managing to be competitive during the season despite the rebuild. It goes well at times, not well at others. But at the end of the season, they make the playoffs while managing to SIGNIFICANTLY upgrade the minor league system, restocking it with a bunch of high level prospects. In the playoffs, they knock off the Yankees (A+), then knock off the Rays (A+), then take a 2 games to 1 lead on Houston in the ALCS, coming within 2 innings of going up 3-1 before the wheels come off and they lose. Still....an amazing run to what can only be described as an incredibly successful season. Making the ALCS while removing the financial shackles they were in AND massively improving the farm system all at the same time.
5. Going into 2022, I believe they hoped that Sale and Paxton would be back by now. They didn't foresee the terrible start they'd have, when at times there was like one or two guys only doing any hitting at all. I think they thought that Casas might make it to the big club in the second half of the year fully ready for the majors, so they only needed a decent half-year from Dalbec. But Bobby has been a disaster. They signed Story to a big contract (so yeah they DO spend money) to play 2b, and he got off to a terrible start too. But the team bounced back and at one point was in 2nd place with the 3rd best record in the division. Then guys got hurt and they went into this crazy tough part of the schedule with just one of their best starters (Pivetta) even available. Meanwhile, they started to add minor leaguers to the majors club and that's been met with some success with some, but not with others (as we might expect). But despite all their tribulations this year, they're still currently tied for the last WC spot, they have a ton of studs in the minor league system, and a bunch of their AAA guys have gotten valuable major league experience.
I mean, overall, I'd say that Chaim has done a hell of a job. OBVIOUSLY he has made some mistakes. No GM is going to get every move right, not even Cashman. But he's overhauled the entire system, bringing in tons of young talent, and he's done so while keeping the major league club competitive. But this year, even if they played great, they'd still be getting killed by the Yankees, given their historic season so far. So all it is about is making the wild card somehow, which right now they're very much in the mix for.