1. The Ricketts' unwillingness to go all in
After narrowly missing the postseason just a year ago, the hope was high that the Chicago Cubs' front office would push their chips in and make some big moves over the winter to catapult the team into the playoff picture. The biggest names in free agency turned out to be an afterthought, and the team continued with his short-deal contracts, which have worked out to this juncture, but in a way many didn't expect.
Shota Imanaga, in particular, was a steal. He has exceeded everybody's expectations. Still, the team's unwillingness to do much more than bring Cody Bellinger back on a deal to bridge the way to Pete Crow-Armstrong was underwhelming with all the big names out there this past offseason. They brought in Hector Neris, who many thought was a good move but was still a bandaid on a bullpen needing severe help. He hasn't been ideal in the closer role, and the team's previous closer lost his spot due to underperforming.
Still, the Cubs refuse to go over the luxury tax, which would help patch the roster holes and truly help them become a winning organization. Meanwhile, the Wrigleyville area is well-invested in for its tourists, who flock to Chicago every year to see a game at the federal landmark, but the buck stops there, literally, as pockets continue to be lined regardless of the outcome of the team's success or lack thereof.
Jed Hoyer has done a great job constructing a farm system that should supplement the major league-level team. However, it must also include a mix of veteran All-Star caliber players. Of course, he can only do so much financially with what he has at his disposal, which is only green-lit from the very top. The Cubs' best players are mere role players on another team. They need a Shohei Ohtani, a Ronald Acuna Jr., or a Bryce Harper player. The longer the Ricketts don't spend top dollar on superstar talent, the more disappointing life will get as a Cubs fan. The franchise is worth more than ever, and there's little reason not to invest in the product on the field.