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Looking Back On Theo Epstein's Cubs Tenure 10 Years Later

Theo's legacy is forever cemented in Chicago.
Theo Epstein Cubs

Photo: Charles Rex Arbogast

Today is the 10-year anniversary of the hiring of former Chicago Cubs' President of Baseball Operations Theo Epstein. Epstein will forever have a legendary place in Chicago sports history as the guy who built the Cubs 2016 World Series team, the team that finally broke the championship drought.

Epstein joined the Cubs front office at a very dark time for fans. There was no direction for the franchise.

The farm system ranked near the bottom of the league. They hadn't developed any homegrown talent in years. Outside of Starlin Castro, many Cubs fans watched players like Felix Pie and Corey Patterson never live up to expectations.

The Cubs' top 10 prospects after the 2010 season included names such as Brett Jackson and Josh Vitters. We all know how those panned out.

Their payroll was in shambles, the third-highest in baseball after the 2010 season. After Theo Epstein's hiring in the 2011 offseason, momentum slowly started to shift in the Cubs direction but the franchise had to be completely revamped.


It started with the trade for Anthony Rizzo, who quickly became the Cubs' No. 1 prospect. Rizzo and right-hander Zach Cates came over to the Cubs in exchange pitcher Andrew Cashner and outfielder Kyung-Min Na. At the time, the top-tier free agent targets on the market were Albert Pujols and Prince Fielder.

Instead, the Cubs invested in Rizzo, who played 49 games and hit .141 with the Padres before the trade.

Fast forward 10 years and many Cubs fans consider Rizzo the modern-day version of Mr. Cub Ernie Banks. Rizzo was the glue that kept the Cubs together in their playoff runs in 2015 and 2016. Epstein was hired on October 12, 2011; Rizzo was traded for on January 6, 2012. Epstein did not waste much time in changing the roster.

Class Is In Session

The 2012 season was probably one of the worst seasons for anyone reading this. The Cubs lost 101 games as they were rebuilding their farm system and selling off as many assets as they could to benefit the future.

Epstein moved fan-favorite Ryan Dempster to Texas for Kyle Hendricks and Christian Villanueva. Hendricks went on to become a solid contributor, posting the lowest NL ERA in 2016, earning a victory after a stellar Game 6 performance in the NLCS, and starting Game 7 of the World Series.

The Snake

Cubs fans will never forget arguably the most lopsided trade in franchise history, sending Steve Clevinger and Scott Feldman to the Orioles for pitchers Jake Arrieta, Pedro Strop, and cash on July 2, 2013.

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Feldman was on a one-year deal, which the Cubs planned to move before the trade deadline to acquire future assets back if he performed well enough for a team to need in the playoffs. His half-season with the Cubs landed them a future Cy Young Award winner and a reliever that was as consistent as any elite reliever for seven seasons in the bullpen.

Fowlers Howlers

In the 2014 offseason, the Cubs traded Luis Valbuena, an infielder Epstein claimed off waivers two years prior, for Dexter Fowler, an outfielder that went on to become the club's leadoff hitter the next two seasons.

Forgotten Transactions

We know Epstein signed Jon Lester and Ben Zobrist and drafted Kris Bryant, Kyle Schwarber, and several other contributors to the 2016 team, but what other moves happened that makes Epstein that much better at his job than most front-office executives?

Jed's Impact

Only 14 days after Epstein was hired, Jed Hoyer resigned from the Padres and teamed up with his old friend Theo in Chicago as the Cubs' GM. Hoyer's most notable move as the GM with San Diego was with Boston when Epstein was still at the helm, sending Adrian Gonzalez to the Red Sox for pitcher Casey Kelly, outfielder Reymond Fuentes, Eric Patterson, and Rizzo. In some ways, this friendship is the reason Rizzo had the opportunity to become a staple in Chicago.

The Spanish Cubs

Epstein selected reliever Hector Rondon from Cleveland in the Rule 5 Draft in 2012. Rondon was the Opening Day closer for the Cubs in 2015 and 2016. He closed out games fans still talk about to this day, including the NLDS clincher in 2015 against the Cardinals.

People Forget

The Cubs signed starting pitcher Jason Hammel in February of 2014 with the idea of potentially moving him at the trade deadline like Epstein had done so many times already to that point.

Before the 2014 trade deadline, Hammel and Jeff Samardzija were included in the deal for Addison Russell, one of baseball's top prospects entering 2015. We know Russell was a key piece to the Cubs World Series run, despite the reasons for the Cubs downfall years after the World Series. What many forget, however, is Epstein re-signed Hammel after the 2014 season and the righty was a key piece to the Cubs making the playoffs in 2015 and 2016.

Setting The Standard

There were more moves that helped the Cubs win the World Series in 2016, but above all, Epstein's magic leading the front office created a standard Cubs fans never had.

He created a culture of striving for the best.

The Cubs are now in a transition where they have moved on from their core pieces after disappointing endings in 2018, 2019, and 2020. Epstein has moved on to bigger things within baseball's core office, leaving Hoyer as the guy to shift momentum back to the Cubs way.

The second half of 2021 was not fun compared to what Cubs baseball has been over the last seven years, but the franchise is in a better place and set up to succeed in the future behind Hoyer thanks to Epstein's work.

It will be interesting to see how Hoyer rebuilds the Cubs roster, but it seems it will take less time, and Epstein has a part in that.

Better times are ahead, but Theo Epstein's legacy is forever cemented in Chicago.