The Chicago Cubs Offseason Decisions

From Champs to Chumps — The Roller Coaster Continues

After winning the World Series in 2016, the Chicago Cubs had ‘Dynasty’ written all over them. A roster full of young, talented, contract-controlled players and a manager that seemed to get the best out of every person that came through that clubhouse. Everything seemed to be going right, and the feeling of the Chicago Cubs repeating as World Series Champions was oozing throughout Chicago and the MLB.

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Theo Epstein and Jed Hoyer at the Cubs World Series Ring presentation at Wrigley Field

The 2017 MLB season rolled around, and the Cubs looked like they were feeling every bit of the dreaded ‘World Series Hangover.’

After somehow managing to stumble into the NLCS, the Cubs got blown away in 5 games by the Dodgers. The feeling surrounding this team was still the same. The fanbase and the organization still had thoughts of a dynasty. One little bump in the road, but let’s re-focus and get back to the promise land in 2018…

The 2018 season was a bit of an improvement for the Cubs compared to 2017. They finished with a record of 95–68. Good for 2nd in a tough NL Central Division behind the Milwaukee Brewers.

This set up a Wildcard game between the Cubs and Rockies…

The Rockies wound up besting the Cubs in that game which ended Chicago’s season.

After that Wildcard loss, the optimism surrounding this Cubs roster began to fade. Many questioned whether they would make drastic changes going into the 2019 campaign.

No significant moves were made by the Cubs that offseason. They went into the 2019 season with their core of young players still intact. Give or take a couple, but the mainstays of the roster were still in place with Rizzo, Bryant, Baez, Contreras and the pitching staff anchored by Jon Lester, and Kyle Hendricks.

When the 2019 season concluded, the Cubs were on the outside looking in at the playoffs. A team that was once regarded as a budding dynasty, had just missed the playoffs entirely. The fans and the organization began wondering if it was time to blow it up. The overarching sentiment from Cubs fans was ‘Well, at least they wiped away 108 years of losing and actually won the World Series’

While many seemed content with that World Series Championship in 2016, you couldn’t help but be disappointed at how poorly the next 3 seasons had played out.

This brings us to the 2020, Pandemic shortened MLB season. The Cubs were a force to be reckoned with under new manager, David Ross. The pitching was great, and they were finding ways to win close baseball games. The offense on the other hand was nonexistent… They did not have anybody hitting over a .280 batting average for most of the season.

Even with the bats going completely silent, the Cubs managed to win the Division and punch their ticket to the post season…

The shortened season birthed a new playoff format which forced the Cubs to play a Wildcard series even though they were division Champions.

The Wildcard series would be a best of 3, and they had a favorable matchup against the Miami Marlins who were playing with minor leaguers for a good portion of the season. This of course was due to numerous positive Covid tests throughout the organization.

The optimism for the Cubs and the fanbase was coming back, and an extended playoff run was well within the cards… However, after losing 2 straight games to the Marlins at Wrigley field… the season was over. Just like that.

The timeline for the Chicago Cubs looks like this.

- 2016: World Series Champions

- 2017: Lost in NLCS

- 2018: Lost in Wildcard

- 2019: Missed Playoffs

- 2020: Lost in Wildcard

An organization with hopes of becoming a dynasty was simply a one hit wonder.

After disappointing seasons in 2017, 2018 and 2019, the Cubs never made significant roster changes. There was always buzz surrounding the possibility of trading away one of their core pieces. Kris Bryant in particular. However, no move was ever made. They continued to ride the horses that washed away 108 years of losing.

That is all going to change this offseason. The Cubs have numerous tough decisions ahead. From contract negotiations to the always prevalent trade options. The Cubs must decide whether they are going to blow it up and start fresh or attempt to make slight changes that could positively alter their trajectory moving forward.

The way it is looking right now, the Cubs have massive decisions to make on each of their core players. This roster could be completely overhauled leading up to the 2020–21 season. It has recently been reported that the Cubs are open to the prospect of trading any of their veteran players. This includes Javy Baez. It seems as if nobody on this roster is ‘Untouchable’

Anthony Rizzo and Javy Baez are entering the final year of their contracts. The Cubs focus should be extending these two players rather than trading them away. Rizzo and Baez are what make this team go. Offensively and defensively. I would like to see them continue their careers in ‘Cubbie Blue’

Kris Bryant will likely be traded this offseason. He has been the centerpiece of trade discussions since his MVP season. While the Cubs could have received a ton more value in return had they traded him after the 2016 or even 2017 seasons, it should happen this offseason.

Willson Contreras’ contract is up for arbitration in 2022. He will also be trade piece this offseason. Whether the Cubs decide to let him go will depend on what they are offered in return.

Jon Lester has likely thrown his last pitch in a Chicago Cub unform… Classiest of class act moves by him when he opened up “Jon’s Tab” at local bars around Chicago in which he paid for $47,000 worth of Beer for Cubs fans as a ‘Thank You’ to the City.

Other major players that contributed for the Cubs during their World Series run such as Kyle Schwarber and Jason Heyward could be on the move as well. If the Cubs do decide to part ways with them via trade, it will signify which direction this organization plans to head moving forward.

This offseason for the Cubs should be a telling one. With dynasty aspirations well in the rear-view mirror, it is time to get back to the basics. Building a well-rounded roster. This will not be an easy task as it looks like Chicago Cubs players will not be the only people in the organization that are on their way out of town.

It has now been made official that Theo Epstein will step down from his position as President of the Chicago Cubs. Jed Hoyer will take his place moving forward. The cruise director that orchestrated a Cubs roster that won the World Series in 2016 is gone just as quickly as he arrived. This news came as a shock to many fans as it was reported that he would wait until after the 2020–21 season to depart. This should signify a new era in Cubs baseball. While Cubs fans are forever indebted to Theo for what he brought to the City, it is exciting to see what the future has in store.

All in all, this Chicago Cubs roster and front office will receive a much-needed facelift in the coming months… Cubs fans will always be left wondering what could have been…

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Avid sports enthusiast creating content for the average sports fan

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