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Chicago’s Curse Is Broken: What’s Next?

Patrick Gorski-USA TODAY Sports

Three things Theo Epstein & Co. will address this offseason that could affect their plans for the future.

Theo Epstein and Joe Maddon recently accomplished a feat no other tandem of manager and front office executive have done for the Chicago Cubs in the last 108 years: win a World Series.

Epstein’s accomplishments should not be overshadowed by the Cubs 108 year drought alone, as Epstein has ended a collective 194 years of droughts between the Cubs and Boston Red Sox. He did so with a plethora of talent that dominated from their 27-9 start, to their league-leading 103 regular season wins.

Jon Lester and Kyle Hendricks were Cy Young candidates after finishing with tremendous pitching stats—202.2 IP, .256 BABIP, and 4.3 WAR for Lester and 2.08 BB/9, majors-best 2.13 ERA, 3.2 FIP, and 4.5 WAR for Hendricks. Anthony Rizzo and Kris Bryant impressed on the offensive side for Chicago on their way to MVP Caliber seasons — top-five in the NL in HR (39), RBI (102), wRC+ (149), and WAR (8.4) for Bryant and 5.2 WAR, 32 HR, 94 RBI, and a career-high .292 BA for Rizzo. 

With the talent-filled North Side roster, many believe that the time for the Cubs dynasty is now. But a dynasty is easier said than built. These are the questions that Epstein & Co. must address to prolong their championship window:

Who Will Be Playing Center Field For The Cubs In ‘17?

 Jerry Lai-USA TODAY Sports

Dexter Fowler filled in admirably after free agent talks with the Orioles fell through, and came back to Chicago on a “prove it” contract. Fowler hit a slash line of .277/.393/.449 with 13 HR out of the leadoff spot, posting solid leadoff hitter numbers in BA (.277), HR (13), and RBI (48). But with championship players come championship caliber contracts. Fowler will be testing the free agent market after the great season and figures to cash in more handsomely than the $8 million that he signed for before the season. Fowler is projected to draw a contract of $54+ million over three years, according to Spotrac, second to only Yoenis Cespedes among center fielders. Because of the price tag, the Cubs should not re-sign the 30-year-old outfielder, but promote in-house.

The Cubs sport a stable full of solid outfielders, including World Series MVP Ben Zobrist, Gold Glover Jason Heyward, and young studs Kyle Schwarber, Albert Almora Jr., and Jorge Soler; even Willson Contreras doubles as an adequate left fielder when he isn’t catching. The best option would be to move Heyward to center, who had four Gold Gloves in the outfield during his time with Atlanta, St. Louis, and Chicago. While Heyward may be a detriment at the plate for the Cubs, they have the firepower to pick up his offensive deficiencies and allow him to support the team on his defense (14th in the majors in defensive runs saved).

Do You Go All In On Aroldis Chapman Or Do You Let Him Walk?

Ken Blaze-USA TODAY Sports

Chapman’s time with the Cubs was very inconsistent. He saw exclusive work as the closer during the regular season with the Cubs, going 16/18 in save opportunities with a .83 WHIP, 1.01 ERA, and 46 strikeouts in 26.2 innings of work. The postseason saw a very erratic Chapman, who gave up more earned runs (six) than he did in the regular season (three). Chapman also had three blown saves, including one in Game 7 of the World Series. Even with the blown saves, Maddon has shown how much he trusts Chapman, putting him in 13 of the Cubs 17 games.

More compelling was the lack of trust he had in incumbent late inning pitchers Hector Rondon (2.1 IP in the World Series) and Pedro Strop (2 IP). With the mistrust in Rondon and Strop, Maddon has shown that come next August he could possibly look for another closer on the trade market if talks with Chapman fall through, or look to other top free agents Kenley Jansen and Mark Melancon to fill the void should Chapman leave. 

With this mindset, it is much simpler for Epstein and Maddon to go all in on Aroldis Chapman as their closer for this championship window. With a market value projected between $80-100 million over four to five years, the Cubs should pay for a pitcher in his prime who has the highest K/9 in a career of any pitcher who has thrown 75 innings or more since 1871. That would certainly be a bargain. 

Looking at the market for closers, with the marquee names besides Chapman being Kenley Jansen and Mark Melancon, Chapman has not only outperformed both pitchers but only comes at a slightly higher price than those two closers. The best option would be to try and re-sign Chapman before another team gets the most potent bullpen weapon for their own postseason run.

Who Is Going To Be The Fifth Starter In The Cubs Rotation In ‘17?

Tommy Gilligan-USA TODAY Sports

With incumbent fifth starter Jason Hammel no longer on Chicago’s roster, a new pitcher will have to step up and follow Kyle Hendricks, Jon Lester, Jake Arrieta, and John Lackey in the Cubs rotation. The market for a “depth starter” in the five spot is incredibly thin, with mediocre pitchers demanding anywhere from $10-15 million from a team. 

Epstein can be frugal about this decision and again, like the center field position, promote in-house until top pitching prospect Dylan Cease is ready to debut (projected 2018 callup). Trevor Cahill can be re-signed for the $4.5 or less he signed for last season; last time Cahill started a full season (more than 30 starts) was in 2012, when he threw 200 IP, and produced a 3.85 FIP, 0.72 HR/9, and 13 wins to the Diamondbacks while posting a 2.6 WAR. Another option, and most likely scenario, will be deploying Mike Montgomery as the last starter. 

Montgomery, like Chapman, came over to Chicago over the summer in a trade with Seattle. He started 16 games for the Mariners last year and posted two complete games, .290 BABIP against, and a 16.2% strikeout percentage in 90 IP. Chicago isn’t going to ask their fifth starter to post ridiculous numbers the way the other four starters do, and Montgomery will be a nice cog in the rotation that will be able to chew up innings throughout the season and be a serviceable bullpen piece for their next World Series run.


Overall, the Cubs have the tools to build a dynasty but need to address these questions to maintain their short and long term success. Maddon and Epstein are executive wizards who have proven their ability to answer the toughest of questions. By signing Chapman to a long term deal, Maddon will have his cornerstone in the bullpen for upcoming playoff runs. But Chicago could miss out on the three prized closers if they wait too long for Chapman to make his decision. 

The young outfielders filling the spot Fowler leaves must keep progressing; Heyward has to hit better than .227, Soler must prove he can stay healthy, and Schwarber has to figure out how to play the outfield if he wants his deadly bat to have an everyday spot in Maddon’s lineup.

Edited by Jeremy Losak, Jazmyn Brown.

Who is credited for the save in the Cubs' Game 7 win over the Indians?
Created 11/19/16
  1. Hector Rondon
  2. Aroldis Chapman
  3. Jon Lester
  4. Mike Montgomery

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