Jed definitely hasn't been perfect, but in order to win you basically either need good prospects turning into good cheap MLB players (or trade for good MLB players) and/or enough payroll to buy good players in FA. Nico, Steele, and Morel isn't enough pre-arb players, and Cubs tax payrolls each year since 2021 have been ranked 15th, 12th, 10th, 9th, and now 12th in 2025.
Even the best FO's would have a tough time sneaking into a wild card spot under those conditions IMO. I think if Jed had spent wiser on his 1-2 year type deals we could have maybe hit 86 wins the last 2 seasons instead of 83 wins, but it's hard to have seen a path to 90 wins unless the budget was expanded or they traded most of their good prospects they've acquired since Darvish.