Chicago Cubs may implode under Theo Epstein this offseason

The Chicago Cubs are struggling to make moves early on in the offseason. The reasons that many are overlooking may surprise you.

In recent years, the Chicago Cubs have struggled to light that postseason fire that drove the team deep into October for several years. From situations like scratching through a tough NLDS against Bryce Harper and the Washington Nationals in 2017 and losing the NL Wild Card game a year later, to missing the postseason completely in 2019, it looks like the Cubs have their work cut out for them. New Cubs skipper David Ross, may very well find himself on the wrong end of a potential World Series window.

Even with Ross at the helm, questions still loom whether or not this first-timer has what it takes to lead the team he played for during their 2016 World Series run back to the promised land. With more veteran choices like Joe Girardi, some were left scratching their heads. Although I see this move in a slightly different light; maybe the Cubs need a fresh face that knows how to bring teams together.

With the drive that Ross will undoubtedly have going into 2020, my only curious itch that needs to be scratched would be seeing what level of possible dominance the North Siders will display. Ross will likely be aggressive out of the gate in hopes the rest of the NL Central will be easily caught off guard early in the season. So as many wonder, even though this writer is a pessimist, Ross may be the revival we need here in Chicago.

Chicago Cubs: Theo Epstein needs to pick up the pace as all eyes fall to him

As the new 2020 season approaches, Chicago Cubs President of Baseball Operations Theo Epstein is under probably the most pressure he has felt since delivering the Cubs their first World Series title in 108 years.

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Even though Epstein’s contract is set to expire following the 2021 season, I am not sure that anyone in his position would be taking this season lightly by any stretch of the imagination.

Throughout his tenure atop the Chicago brain trust, Epstein has consistently stated that he will do what is right by the team and may not follow his well known 10-year plan.

So in my mind, one question is left for Epstein: Do you stay or do you go? If we are honest with ourselves about the team’s chances on signing big name free agents this offseason as well as broadening their farm system, then we should face the harsh truth that Epstein is most likely an ex-Chicago baseball President of Operations come the conclusion of the 2021 season.

So, to make sense out of everything here today, I give you my unbiased opinion on the Cubs future. They are entering the year in my head with a feast or famine mindset. They have to deliver – or a reckoning will come calling.