What is the next move for the Chicago Cubs?

When Theo Epstein first decided to leave Boston, after a run of six playoff appearances and two championships, yet none in the last three, he stated in an op-ed to the Boston Globe that “it had nothing to do with September,” referencing the Red Sox infamous 7-20 finish to the season to miss the postseason in 2011.

That was likely a half-truth. In reality, Epstein did want a new challenge, and despite the fact the current core he constructed was largely stagnant and needed a fresh set of eyes, he still wanted a new curse to break, so to speak.

In many ways this era in Chicago has mirrored his Boston experiences, and this will force the Cubs as an organization to look at themselves in the same way that Boston had to struggle through an identity crisis when Epstein left in 2012.

Looking at the roster in Boston at the end of the collapse, it was clear why it was a convenient time to jump ship. In the offseason before, he dealt Anthony Rizzo to the Padres for Adrián González, a deal lopsided enough that it would more-so benefit his future self.

Carl Crawford was signed to a $142 million deal that, as we all remember, made him immediately shrink from a perennial MVP candidate into a replacement level player. The pitching staff was incredibly vulnerable at the same time, and the rest was history. The collapse ultimately forced out manager Terry Francona, as well, and a new chapter begun.

Not as dramatic as 7-20 but still dramatic were the events of this weekend, where the Cardinals swept the Cubs in a four-game set to push their playoff odds from 76.7% to 2.6%, their lowest mark since the end of the 2014 season. It’s not 2011’s 1 in 278 million collapse, but still quite the drop. It’s the first time they suffered five straight one-run losses since 1915.

Looking at everything that went wrong for the team projected to win 85 games: where do you start? The manager is usually the first to fall on the sword, meaning Joe Maddon will likely be on to greener pastures. That’s usually just a surface-level response, both because Maddon himself probably was tired of the relationship between him and the front office and ownership, and because it gives ownership itself a good thing to point to that they’re taking the matter more seriously. Yet there are structural issues that loom much larger.

The issue with “big contracts” are much different than a decade ago, and as the economics of the game have changed, so has the math for what the big market teams could be able to spend. From 2003 until the time Epstein left almost a decade later, the team’s revenue increased $146 million. In just the time since the lowest point of the rebuild in 2013, their revenue has jumped $180 million, and their valuation an estimated $2.1 billion.

With that the team has retracted in financial obligations, and Epstein has largely obliged on whiffing on any transaction where money is available. Yu Darvish, while much better in his current 90 ERA- season, still has a ways to go on a six-year deal after having only tossed 218 23 innings in the supposed-better first two.

That in isolation wouldn’t be the end of the world! Yet after trading for Cole Hamels last season, which added $20 million to the 2019 club, Tom Ricketts, last offseason, “point[ed] to Hamels’ option, the escalating salaries of arbitration-eligible players like Kris Bryant and the need to earmark money for down the line to retain their own players” as to why the faucet would shut off for Bryce Harper and Manny Machado, who, by the way, have put up a collective 7 fWAR, about the margin of error they missed the postseason by.

The crumb-like signings of Tyler Chatwood, Brandon Morrow, and the midseason acquisition of Craig Kimbrel, did not pan out as expected. Jason Heyward has yet to have a 2+ fWAR season since coming to Chicago. The farm system will likely be featured in the back-third of the pack this spring, despite the fact that Nico Hoerner could be a future bright spot.

So there’s a mix of factors contributing to a frustrating year, and it’s not just Maddon or Epstein, though an overhaul in strategy is surely needed. Sure, the core will need raises as their arbitration years pile up, but those are the silver linings of the team. Bryant was largely back to regular form, hitting to a 134 wRC+ in a full season. The group of Bryant, Anthony Rizzo, Willson Contreras, Kyle Schwarber, and Javier Báez put up a collective 20.2 fWAR, good for 82% of the collective position player performance. To boot, none of them are even close to their top-five players in salary.

With Ben Zobrist, Cole Hamels, and Steve Cishek coming off the books, they should see $40 million free up in payroll, offset partially by the raises for the aforementioned squad. Yet if the team is unwilling to spend when it counts, they may largely stand pat once again, claiming the signing of Kimbrel was all they could muster, and watch the likes of Gerrit Cole and/or Anthony Rendon head on over to another team.

Which would be just one piece of the puzzle. Teams like the Yankees and Dodgers have pulled players like Max Muncy and Luke Voit out of a hat, and the Astros have built a name on player development themselves, so if they don’t plan to open the checkbook, the question of getting creative with a relatively weak farm system ultimately remains. To be fair, the acquisition and flourishing of Nicholas Castellanos was an excellent start, and that would be a slam-dunk offseason deal to be made if there was one.

The 2012 Red Sox had Jon Lester, Dustin Pedroia, and Jacoby Ellsbury, not exactly formidable in comparison to a Cubs core that could ultimately have multiple Hall of Famers. With that much to work with and some obvious holes to fill in both the rotation and in adding another bat, this only mirrors Epstein’s tenure in Boston, it doesn’t copy it. History doesn’t repeat itself, it merely rhymes.

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