The Cubs largest contract in history ranks 12th out of the 15 in the NL. Only the Pirates, Cardinals, and Giants have also failed to ever spend 200 million on a player. They move up to 19th in all of MLB if you count all teams, but they're still in the bottom 3rd of the league.
Jed's team last year failed because he thought 7 million would fix the bullpen, and that Hosmer, Mancini, and Barnhart belong on a good baseball team. The Cubs have lost 7.5 wins from last year's team. Now some things did go well
Suzuki had a huge step forward. Tauchmann seems to be a serviceable 4th/spot starter. Swanson put up 4.9 WAR. They have a top 5 farm system, but it's drastically short on impact talent. Thus far, Ross failed to extract much value from the kids coming up, but hopefully Counsel changes that.
It's pretty clear we're far behind the Dodgers and the Braves at this point. The Braves develop, trade, and extend far better than Jed and the Dodgers are willing to spend money. Those should be the teams we're worried about, because a team with the Cubs revenue and pricing structure shouldn't be crying poor.