Cubs face a plethora of daunting questions this offseason

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.