It feels stupid to bring up Zips on October 6th, but going into the year, with a healthy Steele, Zips had us as the 9th ranked offense and the 18th ranked pitching team (17th for SP, 21st for relievers) in baseball. There was one obvious position on the offensive side to upgrade, we made some sort of attempt to get Bregman, we didn't get him, and we did basically nothing else with the money (Flexen and Turner technically signed after Bregman, but....yeah.) The list of pitchers who signed after the Bregman deal is admittedly not impressive, basically just Quintana and Patrick Corbin, but A. it was clear we needed at the very least innings, if not talent, and B. it's Jed's job not to be left with a pile of money and a weakness he was almost certainly aware of.
This is probably an unnecessary shot, but it's almost like he got high on his own supply with the (both objectively good) Swanson and Bellinger contracts, waiting out the market and getting a good player for less than he maybe would have cost otherwise. But he didn't make enough improvements in the offseason, and he certainly didn't make enough improvements at the trade deadline.
(I'm also aware that if you would have asked me about this topic in July I would have said that upgrading from Colin Rea to Shane Bieber or Zac Gallen would have improved our WS odds from like 6% to 8% so who cares and I'm in about as close to meatball mode as I'm going to be. But I think the truth is somewhere in the middle.)