High B, maybe a B+
I think they did a good job if you focus on the period of time from 11/1 to the middle of February. Which is technically the question. In hindsight the Kittredge situation doesn't make sense, and I don't love how the Shota situation played out. Going from Tucker to Bregman was clever and while I think we're probably a slightly better team with Shaw at third, Tucker in RF, Seiya at DH, and generic backup MIF on the bench than we are with Bregman 3B/Seiya RF/Ballesteros DH/Shaw Util, we also have an extra $25m or so annually to play with. We finally turned a blocked prospect into a pitcher, and we went after a very high upside guy that gives us a dice roll on a game one starter.
In terms of the bullpen, whether it's 'fixed' remains to be seen, and it is very much a matter of cleaning up their own mess. Similar to the overarching concerns about the roster cliff. The system is depleted, but obviously they get credit for PCA, Shaw, Horton, Busch, etc. I think in a world where Ballesteros and Caissie were relatively viewed the same in terms of overall value, I probably would have opted to trade Ballesteros (or go get a DH bat and let him catch 120 games in Iowa).
Ultimately, on the one hand I was calling for the big bat signing and the pitching trade, and we got that, but on the other hand I'm not sure we're better than what we were in November. Status quo for a 92 win team is fine, but the top end of the grading system is reserved for improvement.