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Repeat Roadblocks: Cubs Offseason Challenges

With a World Series title finally in the bag, Cub fans aren’t just hopeful for a championship repeat – they’re expecting it. Although Chicago is in a position that leaves the majority of the league in envy, some questions still surround the team this offseason. Repeating a feat that was 108 years in the making is no small task.

With fan-favorite and clubhouse linchpin David Ross retiring, the full-time catching duties will be split between Willson Contreras and Miguel Montero. Presumably, Kyle Schwarber will make his move to the outfield permanent and compete for a starting spot in the spring.

The veteran Montero expressed some discontent with the role he played during the postseason, citing manager Joe Maddon’s failure to communicate expectations with him. Despite his low production during the regular season, Montero believed he should have played a bigger part down the stretch in October.

Even though he was used sparingly, Montero’s contributions were significant, hitting a pinch-hit, go-ahead grand slam in Game 1 of the NLCS and coming off the bench to drive in a run in Game 7 of the World Series.

Moving towards Spring Training, it will be interesting to follow the Montero situation. He is in the last year of a $60 million contract he signed with Arizona in 2012. Despite the $14 million Montero is set to make in 2017, he may be stuck behind the younger, more offensively gifted Contreras.


With Dexter Fowler testing the waters of free agency, the Cubs may be forced to replace their lead off hitter this winter. Although there is a good chance Fowler returns to Chicago, the Cubs must prepare for other scenarios.

It is unlikely that Joe Maddon would move four-time Gold Glove winner Jason Heyward out of right field, even though he started twenty-one games in center this past season. Jorge Soler and Kyle Schwarber haven’t played an inning of center field in the majors and Ben Zobrist hasn’t played center since 2014. Matt Szczur, Albert Almora Jr., and Chris Coghlan are all viable options in center, but may not be worthy of an everyday starting spot.

The only other players on the roster that have outfield experience are Willson Contreras, who occasionally played left field, and Kris Bryant, who is all but locked in at 3rd base.

Maddon could choose to platoon a pair of center fielders. He frequently looked to Coghlan against right-handed pitchers last season, even starting him in Game 1 of the World Series against Corey Kluber. Almora Jr., who has perhaps the brightest future of any Cubs outfielder, may develop enough to earn the full-time starting job.

The Cubs shouldn’t worry about signing a center fielder in free agency, unless it’s Fowler. As much as fans may like the thought of bringing in Yoenis Cespedes, the front office is going to want to invest carefully after a spending spree last offseason. Other potential center field candidates aren’t worth chasing this offseason. They currently have plenty of talent in Chicago, so it would be unnecessary to bring in a free agent outfielder not named Dexter.

With or without Fowler, just as we saw this past season, the Cubs outfield could look different on a day to day basis. Maddon has a unique group of versatile players who excel at multiple positions. This means that he has the freedom to move a guy like Bryant to two or three other positions if necessary. He can choose to put more offensive threats in the outfield, like Schwarber or Contreras, and avoid major consequences on the defensive end.


The Cubs did not pick up the option on starter Jason Hammel, which means that there will be an empty spot in baseball’s finest rotation.

The front end of Chicago’s rotation is unhittable when things are clicking, and still hard to hit when they’re not. It’s going to be a toss-up determining the Opening Day starter with Jon Lester, Jake Arrieta, and Kyle Hendricks each vying for the spot.

After that deadly 1-2-3 punch comes John Lackey, who is not your average number four starter. He’s coming off of a career best year, but recently turned thirty-eight. Approaching season fifteen, asking for 180 innings might be too much.

The Cubs have to prepare for Lackey’s age to catch up with him and solidify the back end of their rotation. They could try to move Mike Montgomery into the rotation, or stretch out Carl Edwards Jr., who last started in AA two seasons ago. Both showed promise in the latter stages of the season and into the World Series. After Aroldis Chapman’s Game 7 meltdown, Edwards and Montgomery helped close out the game for Chicago.

It is unlikely that Chicago would dive into the free agent market to find a fifth starter, but not out of the question. It seems that they would try to work with one of the pieces already on the roster or, as a last resort, dig into the farm system.

The path to a title is a winding one. Chicago knows that better than anyone. If they wish to replicate their success, they have some work ahead of them this offseason. Lucky for them, they just might have some extra time to figure things out this winter if the collective bargaining agreement fiasco isn’t fixed.

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