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Theo Epstein’s Legacy in Chicago Will be Dictated by the Success of His Decisions this Offseason

Even with all the prior success Theo Epstein has had running the Cubs, this offseason's decisions and how effective they are will permanently shape how he is remembered in Chicago.
Theo Epstein Leaving Cubs

Photo: Winslow Townson/USA Today Sports

After the 2017 season ended, there was not one single fan in Chicago that could reasonably criticize Theo Epstein’s decision making as President of the Chicago Cubs. It took him three years after he was hired in October of 2011 to turn an organization that was touted as the “lovable losers” of baseball into the juggernaut that was dominating the Major League Baseball landscape. From 2015 to 2017, the Cubs won an average of 97.3 games (best in baseball), had three straight NLCS appearances, and won one World Series title. It was a remarkably quick turnaround in which Theo and GM Jed Hoyer practically made zero mistakes. Fast forward two years later, and that narrative of being immune to criticism from the fanbase has completely flipped. As Theo announced that Joe Maddon would not be retained as manager for the 2020 season, most fans were quick to side with Maddon and cast blame on Theo for the Cubs’ failures the past two seasons. I for one disagree with that notion, but that doesn’t mean I think Theo shouldn't shoulder at least some accountability. Theo preached the day he was hired about the organization's goal of having sustained success, and the last two seasons have fallen short of that mantra. A lot of that is on Theo, and he was quick to admit this in his press conference two weeks ago.

While fans criticizing his decisions the past couple years is warranted, the notion that he should be fired, which I’ve seen plenty of this past month, is beyond absurd. Theo is as good as it gets in terms of executives in major league baseball and he has proven it dating all the way back to his days in Boston. He has a Hall-of-Fame track record, and there's really no argument to be made otherwise. Two seasons accompanied by a few mistakes does not change that. I mean, do people misremember how flawless his decision making was from 2012 to 2016? To jog the memory of those fans who forgot, here’s a table to remind you of the trades he made in that timeframe. Every single one of these trades generated more return than the value given up, and most were not even close.


In addition to these trades, he signed Jon Lester and Ben Zobrist in free agency, as well as drafting Kris Bryant and Kyle Schwarber. The overall strategy Theo and Jed set out was very innovative and genius. In an era that valued drafting pitching, they decided to do the exact opposite: build a foundation of talented position players both through the draft and trades. The rationale was simple: Building through young pitching was too risky due to the high prevalence of Tommy John surgeries ruining careers and the inability to forecast which young pitchers were prone to these types of injuries. Then, once these talented core position players finally made it to the big leagues, he supplemented them by acquiring proven healthy pitching through free agency and trades (i.e. Jon Lester, Jake Arrieta, Kyle Hendricks). This strategy has since been replicated by other organizations, namely the Astros. Almost every single decision Theo made during 2012-2016 was flawless and was a direct reason the Cubs won the World Series.

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What has gotten Theo into trouble recently is exactly what rendered so much success in the trades in the above table, except that the risky moves that were consistently hitting in the Cubs' favor stopped doing so. For example, trading top prospect Gleyber Torres, the current second basemen for the Yankees, for a four-month rental in closer Aroldis Chapman is as risky as it gets. Theo knew the Cubs had no intention of signing Chapman long-term after the 2016 season, but he took a massive, calculated risk because he understood the Cubs could not win that 2016 World Series without a significant upgrade in the bullpen. In this case, the risk worked out. I understand not all of these risks have panned out, which I will get into later, but wouldn't you rather have a leader who's willing to take calculated risks that could potentially look bad in the future if it doesn't result in immediate success? Andrew Friedman, President of the Los Angeles Dodgers, is notorious for hoarding cheap prospects and not taking these types of risks because going "all in" hurts future success. Need I remind you which team has won a World Series in recent years and which is sitting on seven consecutive division titles with nothing to show for it? I am willing to bet any Dodgers fan would trade places with the Cubs fanbase right now because of one simple fact: winning the World Series is hard, even if you are the proverbial 'best team in baseball' heading into the playoffs. If Theo replicated Friedman's strategy, sure the Cubs would be better off right now with Gleyber in their lineup, but that 2016 ring also would not exist. I'd rather have a guy who's willing to make the tough decisions to win the last game of the season even if it means sacrificing some future success.

Theo knew there was a chance Gleyber Torres could turn into an All-Star. Instead of worrying about how bad the decision would look in three years if the Cubs fell short of a World Series in 2016, he had the fortitude to take a bold risk. The risk worked out.

Theo knew there was a chance Gleyber Torres could turn into an All-Star. Instead of worrying about how bad the decision would look in three years if the Cubs fell short of a World Series in 2016, he had the fortitude to take a bold risk. The risk worked out.

Since that Gleyber Torres trade in 2016, those risks have not panned out as frequently. While he still has made great moves recently in acquiring Cole Hamels and Rowan Wick in deals that were very lopsided in the Cubs’ favor, there are three examples where the opposite has been true. Trading prospects Eloy Jimenez and Dylan Cease for Jose Quintana at the 2017 deadline has not worked out the way Theo envisioned. This isn’t because those prospects are lighting it up on the White Sox, it’s more about Quintana underperforming for the Cubs. Theo thought he was getting a highly effective, cheap middle of the rotation guy with Quintana. However, Q has been more of a fourth or even fifth rotation guy since his arrival and just finished the worst season of his career. Giving up highly touted prospects like Eloy and Cease requires more production in return, and it didn’t happen. Moving forward, signing Tyler Chatwood two offseasons ago was also a mistake. While he showed some success in the bullpen this year, that pales in comparison to the $13 million he’s receiving annually to be a middle rotation guy. Theo thought Chatwood was undervalued because half of his starts were at Coors Field, the most hitter-friendly park in baseball. The rationale of thinking he would improve significantly due to not constantly pitching in altitude was sound and logical, but it hasn’t worked out. Lastly, trading away second basemen Tommy La Stella to the Angels, who made the All-Star team this year, and signing Daniel Descalso to replace him is easily the worst decision Theo’s made while running the Cubs. Lack of depth was the biggest issue all of this season, and it was partly due to that mistake.

Those three mishaps have played a role in the Cubs underachieving the past two seasons. While there are certainly other reasons, there’s no denying that fact. That’s why this offseason is so crucial for Theo and Jed. They have a good amount of money coming off the books this offseason, as I pointed out in this article two weeks ago, so they will be making acquisitions in free agency. I also foresee Theo trading from the MLB roster this offseason. Both avenues will be used to induce change, and how effective that change is will impact Theo’s legacy running the Chicago Cubs. Yes, he’s made some mistakes the last couple years, but there’s not one other person I’d rather put my trust in this offseason to lead the organization back to the success it experienced not long ago, and the table earlier proves it. Theo only has two more seasons left until his contract expires. These next two seasons, if he decides to leave after 2021, will decide if he goes down as a Chicago sports legend or the guy who won the Cubs one much-needed World Series and didn’t do much else afterward.

Featured Photo: Winslow Townson/USA Today Sports