Cubs face a plethora of daunting questions this offseason

Will the Cubs bring back Jon Lester for one more go-round in 2021? (Mandatory Credit: Mike Dinovo-USA TODAY Sports)
Will the Cubs bring back Jon Lester for one more go-round in 2021? (Mandatory Credit: Mike Dinovo-USA TODAY Sports)
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It looks like this will be Theo Epstein’s last offseason with the Cubs. (Mandatory Credit: Ray Carlin-USA TODAY Sports)
It looks like this will be Theo Epstein’s last offseason with the Cubs. (Mandatory Credit: Ray Carlin-USA TODAY Sports) /

Is this the year the Cubs finally make some long-coming hard decisions?

After a prompt exit in the NL Wild Card Series, you’d think the Chicago Cubs will finally take a long look in the mirror and attempt to answer some tough questions. With one year remaining on his contract, Theo Epstein faces perhaps his toughest test in the post-2016 era.

Sure, the Cubs brought home a division title in 2020. But at the end of the day, pretty much every key position player underperformed and the pitching staff was erratic for much of the season. Once the team cooled off from its 13-3 start, they never looked like a legitimate postseason threat.

Yu Darvish and Kyle Hendricks ranked as one of the best one-two punches in baseball. But looking past those two, the rotation never inspired a great deal of confidence. Now, with the team all but sure to decline Jon Lester‘s 2021 option and pay him a $10 million buyout and see Jose Quintana and Tyler Chatwood hit free agency, the team has major rotation depth concerns.

Chicago Cubs /
Chicago Cubs / /

Cubs need additional pitching depth behind Yu Dar vish, Kyle Hend ricks

Alec Mills and Adbert Alzolay will undoubtedly get a long look next spring. Of course, Mills made history, throwing a no-hitter this year, while working to aa 4.48 ERA in 11 starts. He was up and down in terms of performance and will need to find more consistency to be a contributor moving forward.

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Alzolay really looked like something. He turned in a 2.95 ERA and averaged north of 12 punchouts per nine in four starts and a pair of relief appearances. Right now, he looks like he could be the homegrown arm capable of claiming a rotation spot we’ve sought for years.

Knowing all this, Theo Epstein alluded to the team’s need to shore up pitching depth. The bullpen wasn’t great – although a late-season Craig Kimbrel resurgence offers hope for 2021. Will it be another winter of bargain shopping or will ownership allow Epstein to make impactful additions to the mix this time around?

Moving on to the offense, there is absolutely nothing you feel really good about right now. Jason Heyward turned in his best offensive season in a Cubs uniform – and that’s a major plus. Ian Happ looked like he was turning a corner, but cratered out as the season wound down, slashing .189/.250/.216 over the final two weeks.

Cubs slugger Kris Bryant battled through injuries this season. (Photo by Dylan Buell/Getty Images)
Cubs slugger Kris Bryant battled through injuries this season. (Photo by Dylan Buell/Getty Images) /

Cubs have to get production from their star players – or else

The ‘core’ of Kris Bryant, Javier Baez, Anthony Rizzo and Kyle Schwarber all struggled. Without those big bats taking care of business, the offense stood no chance of finding success. This entire lineup is predicated on those guys serving as a driving force and creating runs. It didn’t happen and the team paid the price.

Epstein could try to trade from this crop of free agents-to-be. But what return will he get? Not much at this point. Bryant missed considerable time due to injury and wasn’t his MVP-caliber self on the field. Baez was downright horrible – and did major damage to his prospects of landing a mega-deal either in free agency or in contract talks.

We’ve talked about a reckoning for some time. It seems like watching your offense fade late in the season for the third consecutive season would be the final straw, but this isn’t a typical offseason. Finances are a major concern, your ‘trade chips’ have lost a ton of value and a regime change could be on the horizon in the baseball operations department.

dark. Next. A Yu Darvish trade could change everything for the Cubs

Will this be the winter of change? We’ll have to wait and see.

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