The Tepera trade was very solid. Horn is fine and may, possibly, eventually, become a contributor in the Cubs pen in 2023; however, he's a 35+ guy no matter how you slice it. The A's gave up Daniel Palencia who is a better prospect than Horn for Chafin who is objectively worse than Tep.
Cesar obviously hasn't been great, but it would've been a bit short-sighted to just plug Leury in a second and take him out of the super-utility role. The idea of Cesar was that he'd be a league average bat (more pop than contact) with plus defense. Hasn't exactly worked out, but its hard to blame Hahn for that. Picking him up from the second place team in the division that you have a super series with at the end of the year was a nice boost. Looking back, Pilkerton was too steep of a price considering the results both have had, but their is no guarantee that Pilkerton's stuff will play at the bigs during the title window. Regardless, I dont think Pilkerton was netting more than Cesar so their isnt much opportunity cost worry here.
Then obviously, the Kimbrel Trade. If the plan was for an eighth inning guy, there were cheaper ways to do this. If Kimbrel were a guy like 2016 Andrew Miller that would give you 2 innings of shutdown relief every other night then fine. If you wanted to put Kimbrel at closer and move Hendricks into that role, then I'm good with that. Sox talk legend Codi Heuer got absolutely shelled today. Even prior to today I dont think anyone here would rather put him out there in the 8th instead of Kimbrel.
The biggest issue is the Madrigal part. The thought was that Cesar would provide similar value to Madrigal next year, while contributing to the title run this year. By 2023, Jose Rodriguez may be able to be the starting second basemen. To a tanking team like the Cubs, getting an MLB ready asset that wont impact the teams mission of putting a disgusting product out there day in and day out is a dream. The bigger concern is more the opportunity cost of what else Madrigal could've brought back. The right teams had to value a second-base-only guy with a torn hammy who relies on his hit tool. If the Marlins/Pirates/Rockies' scouts aren't impressed with Madrigal you can build a trade around him. Simple as that.
Sure Bryant would've slotted in well, but there was no club option on Bryant and he would almost definitely leave after this year. I also really don't think that Hoyer and ownership would be willing to trade him to the South Side without a huge tax. On the emotional attachment scale, I think TA=Javy, Jose=Rizzo, and Bryant=Robert. Kimbrel is like Hendricks. Love the guy, but he's more of a mercenary than a guy you've been attached to for years. I root for the Sox, but that wouldve hurt me.
There has been and will be debate on what Madrigal should've been cashed in for, but I think Hahn's process was sound here. The starters were dominant prior to the deadline and Lopez has been great as the #6 since. The lineup was producing and still had Robert, Grandal, and Eloy coming back. And the bullpen was very good, but there was a need for another reliable high-leverage guy so that Crochet and Kopech could avoid being over/misused.
From the outside looking in, I think Hahn is a hell of a GM. Like Theo, he will have his warts when you look back at his tenure, but he brought back the Sox from purgatory by nailing the Sale, Quintana, and Eaton trades. If Hahn had a bigger budget, he may have given Zack Wheeler and offer so big that he told is in-laws to give him some space. Hahn obviously preferred Wheeler over Keuchel and that would've been a huge difference in this title window.
If the Sox win the WS, the answer is A+. If not it's a C or worse. Pretty much no matter what he did during the deadline the answer would be the exact same. As for your question, I'd probably go B or C if I had to choose. I think he showed that he can be a somewhat unemotional buyer which is a good thing. I think some GMs would be more attached to their #4 overall pick and wouldn't sell him at an injury discount.