How Theo Epstein Saved the Chicago Cubs

By Chris Katsaros |  @RedLineProject | Posted: Wednesday, March 4, 2020 

Before the Ricketts family purchased the Chicago Cubs on July 6, 2009, they were owned by the Tribune Company. A common criticism among fans was that the Tribune Company did not prioritize winning, and instead cared only about making money.

Predictably, fans were thrilled at the idea of a family owning the Cubs, rather than a media conglomerate. Although they are one of the most popular franchises in North American sports, the way the Cubs organization gained such a large following was frustrating to even the most die-hard fans.

At the time of the Ricketts’s purchase of the team, the Cubs were in the midst of the longest championship drought in North American sports at 101 years.

Tom Ricketts, who runs the organization currently, wasted no time in his attempt to bring a championship to the North Side of Chicago, where the Cubs play at historic Wrigley Field. On Oct. 12, 2011, the Cubs hired Theo Epstein from the Boston Red Sox to their president of baseball operations.

Theo encouraged fans to trust in his plan to bring a championship to Chicago within five years. Cubs fans, already used to years of exclaiming, “this is the year,” bought in to Epstein’s pitch.

While the first few years of the rebuild were difficult, from 2015 on, the Cubs have enjoyed sustained success as one of baseball’s best teams.



So what was Epstein’s plan to accomplish a task that many people believed was impossible?

The process began with the rebuilding of the farm system. Theo selected third baseman Kris Bryant with the second pick in the first round of the 2013 MLB draft. Bryant would go on to win National League rookie of the year in 2015 and the National League MVP award in 2016.



Theo also recognized infielder Javier Baez and catcher Willson Contreras, who were drafted by the previous regime, as valuable assets who would be important to the big league club.

Next, Epstein made key acquisitions through trades that seemed minor at the time they were made.  He acquired Anthony Rizzo from the San Diego Padres, who blossomed into one of baseball’s elite first baseman.

He also acquired starting pitcher Jake Arrieta and reliever Pedro Strop from the Baltimore Orioles. Arrieta was one of the best pitchers in baseball from 2015 to 2017, winning the National League Cy Young Award in 2015.



Finally, Epstein had to sign a couple of free agents to solidify this rebuild as legitimate. The most significant of these signings was on Dec. 15, 2014. The Cubs acquired veteran starting pitcher Jon Lester for six years, $155 million.

With the team finally taking the form of an elite World Series contender, the only missing piece was a manager capable of leading a young core of players. Enter Joe Maddon, who previously managed the Tampa Bay Rays.

Maddon led the Cubs to a 103-win season in 2016. They beat the Giants in the NLDS, then the Dodgers in the NLCS.

On Nov. 2, 2016, while playing in the 10th inning of Game 7 against the Cleveland Indians, Bryant gloved an infield roller and tossed it over to Rizzo at first base. The out cemented the Cubs as World Series champions, the goal that  Epstein vowed to Cubs fans that he would accomplish.

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