Chicago Cubs: This winter might make or break Jed Hoyer

Chicago Cubs management can’t do anything right these days. The trades of three beloved superstars have put Jed Hoyer under the gun. The Cubs roster is gutted, and it’s basically a Triple-A lineup for the remaining 50+ games or so. Fortunately for Hoyer, this winter will give the Cubs a chance to redeem themselves.

Chicago will only have about $50 million or so on the payroll coming out of the 2021 season. There will be money to spend. Both Hoyer and Cubs’ Chairman Tom Ricketts have spoke about financial flexibility moving forward. Now, it’s up to them to prove it.

Jason Heyward, Willson Contreras and Kyle Hendricks are the big contracts for 2022, and quite frankly, nobody knows what the Cubs’ plan is from here. Granted, in Hoyer’s defense, it’s hard to put a hard number on when the team will be good again, given the fact there will be a new CBA and how that will effect players and the market.

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Hoyer has repeatedly stated this will not be a long rebuild, and he needs to prove it. There are names available, the Cubs’ big three obviously, Carlos Correa, Freddie Freeman, Corey Seager, the list goes on. The whole fanbase has a sour taste in its mouth right now, and fielding a competitive team in 2022 is one way to get the fans back on their side.

Chicago Cubs: A path to competitiveness

There is a path to being competitive in 2022, and it involves going crazy this winter, be it with trades or free agency. It’s a matter of how much the Cubs want to commit to it. There’s a theme in all the prospects the Cubs acquired at the trade deadline, and they are all a few years away yet, mostly 2023-24. It doesn’t look like the Cubs have any intention of competing in 2022, at least on the surface.

Hypothetically, if the Cubs can find some starters behind Hendricks for the rest of 2021, like Justin Steele, Keegan Thompson and Adbert Alzolay is already there, they are already ahead of the 2022 curve. Now, say the Cubs sign a guy like Chris Taylor, or Mark Canha, and give a big deal to Correa, and a former Cub, Nick Castellanos, has an opt-out in his contract after this season.

Making some additions like that, plus the presumed addition of top prospect Brennen Davis could make the Cubs a contender for the division in 2022, and they can build from there.

The team could also be players in the trade market, and re-visit the trade talks with the Rays that they had at the trade deadline. It involved the Cubs trading Bryant to Tampa Bay and the Cubs taking back Kevin Kiermaier, plus his salary and some prospects, and possibly Tyler Glasnow. The fan in me says the Cubs should have done that and it would have been a huge blockbuster.

There is a path to competitiveness. The Cubs have options. They have money, the free agent class is good, and they need to make a few moves. Hoyer’s future with the organization could very well depend on it, and fans may stop showing up if the Cubs show no interest in winning.