Chicago Cubs: Theo Epstein has stalled a promising dynasty

CHICAGO, IL - NOVEMBER 04: President Theo Epstein of the Chicago Cubs (Photo by Jonathan Daniel/Getty Images)
CHICAGO, IL - NOVEMBER 04: President Theo Epstein of the Chicago Cubs (Photo by Jonathan Daniel/Getty Images) /

Before the 2017 season began, the start of a dynasty on the North Side seemed inevitable. That’s all quickly changed for the Chicago Cubs, thanks to Theo Epstein’s rash decision-making.

The Chicago Cubs now face a harsh reality check as they enter a long, disappointing offseason. After failing to repeat as World Series Champions in 2017, there are plenty of reasons for fans to be concerned about the direction of this organization.

What appeared to be the beginning of a promising dynasty for the North Siders has quickly evaporated. Since the moment the Cubs won the World Series a year ago, they’ve become a complete shell of themselves.

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The organization’s failure to improve from 2016 falls directly on the shoulders of President of Baseball Operations Theo Epstein. He was the architect of the first Cubs World Series Championship team in 108 years. Yet, he’s also responsible for the regression of nearly the same roster that delivered on the biggest stages of the postseason a season ago.

While improved teams like the Los Angeles Dodgers and Houston Astros are now playing in the World Series, the Cubs are left wondering, “What could have been?”

Epstein took a major gamble following the Cubs’ Game 7 victory over the Cleveland Indians, betting that nearly the same roster, minus a player or two, could deliver a reminiscent championship performance a season later.

Hopefully by now, Epstein has learned a valuable lesson or two about feeling overconfident in his team. Nothing is guaranteed in baseball. Epstein should have seen this coming first-hand before it actually became reality.

Maybe he did see this exact fate approaching the Cubs when they posted a 43-45 record during the All-Star Break. But by that point, Epstein was too stubborn to change the team’s inevitable course of direction.

He had done all he could to justify his wrongdoing of largely staying put throughout the 2016 offseason, but then he decided to swiftly trade away prized hitting prospect Eloy Jimenez, along with the organization’s top pitching prospect, to the Chicago White Sox in exchange for Jose Quintana in early July.

A desperate, rash act to try to save a season that was spiraling out of control quickly thanks in large part to the performance of an underachieving, once reliable starting rotation. In the end, the trade looks bad because Quintana appears to be an average pitcher at best while Jimenez continues to look like a future star in the making.

The Cubs, with all their young talent, could use a few more stars on their roster moving forward. Justin Verlander, who’s been the Astros’ most reliable pitcher this postseason, could have been a Cub instead. If not for Epstein’s stubborn refusal to take on another large contract. At least in this case, Verlander’s contract would have been worth the pay, given how great he’s performed thus far in the World Series.

A series of unfortunate events

There were other warning signs of the Cubs’ 2017 demise that Epstein saw coming but refused to act upon with great precision. The bullpen was probably the most glaring issue that plagued the team all season long, especially throughout the postseason. Yet, Epstein decided not make many notable changes in that department, other than acquiring relievers Wade Davis, Brian Duensing and Justin Wilson.

Trading for Wilson in mid-July turned out to be a major mistake as he performed poorly as a Cub, becoming more of an afterthought.

Also, trading for Wade Davis to replace Aroldis Chapman in the closer role proved to be a downgrade move as well. Only Duensing performed well in his new role as a mid/long reliever, replacing Travis Wood.

But one reliable reliever can’t mask the self-inflicted wounds caused often from Maddon sending out Hector Rondon, Carl Edwards Jr. or Pedro Strop in hopes of preserving a narrow lead late in games.

Of all the recent mistakes Esptein has made, though, none might have been more consequential than having too much faith in his young core of players.

Granted, the Cubs were coming off an improbable World Series comeback victory for the ages. Still, Epstein should have known better than to believe that this Cubs’ roster would simply continue to follow a familiar script of greatness for years to come.

Kris Bryant, Anthony Rizzo, Kyle Schwarber, and Addison Russell all regressed as hitters this season. When the lights shined brightest in the postseason, none of these young talented players came through during pivotal moments. It’s largely why the Cubs are sitting at home now instead of competing in the World Series.

Epstein’s unwavering faith in his young hitters, even as they struggled to drive in runs all season long, cost the organization a chance to address other glaring holes on the roster during the trade deadline. Epstein could have easily packaged a trade involving Schwarber, Baez or Russell for a top-tier starter or reliever. Yet, he refused to pull the trigger, becoming fooled into believing that his core talent would simply play like they did a season ago once they got into postseason play.

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By now, Epstein must be regretting not being more aggressive in pursuing deals to improve his flawed roster. But that’s what often happens when your team hoists a championship trophy. You become complacent, not feeling a need to change what’s been working just fine over the past few seasons. Unless you’re Bill Belichick, who is always looking to improve his roster through trades, even if his team is coming off another Super Bowl victory.

Now, Epstein has an entire offseason to repair any glaring weaknesses to his roster. If that means sacrificing more young talent to become a championship contender once again, then so be it. After all, it’s what both the Dodgers and Astros have done in order to be where they are today.