I think bottom line is the 3 best arms in the org were on the IL, plus some key bullpen signings were hurt too, among other injuries. They got 3 good arms at the deadline but when your rotation and pen is gutted from injury it's difficult to recover.. In 2016 they got Chapman to improve the team, but this deadline they were trying to plug holes from injury.
The team trended poorly going into the playoffs. Their best hitter was hurt etc. horsefeathers happens. If you want to win a ring things need to go right and we just had a lot of bad luck/ timing.
Jed decided to put the money into the offense. He spent big on Bregman instead of an ace pitcher like Cease and given how pitchers get injured these days I think he made the right call. Steele, Horton, Brown getting hurt isn't their fault. Horton was always an arm injury waiting to happen but considering the other picks after him in that draft they took the risky high upside over someone with no standout tools like Brooks Lee.