The Legacy of Theo Epstein: Looking back at one of the best executives in baseball

After stepping down as the Chicago Cubs President of Baseball Operations on November 17, Theo Epstein concluded his successful tenure in Chicago. Although his time is far from over in the world of baseball, Epstein is already one of the most accomplished executives of all time after bringing two World Series titles to Boston and one to Chicago. As the mastermind behind the Cubs’ 2016 World Series championship victory that concluded a 108-year championship drought, Epstein solidified his status as one of the best executives in the game of baseball and a Chicago legend. In his time with the Cubs, Epstein acquired many key players during the years prior to the 2016 season and was largely responsible for the Cubs’ World Series victory.

When Epstein signed with the Cubs in October 2011, management tasked him to turn a team that had finished well below .500 the year before into a World Series-caliber roster, undoubtedly a significant challenge. Over the next five years, Epstein made many transactions that created a powerful Cubs roster. One of his biggest acquisitions was first baseman Anthony Rizzo, who was a leader on the team and played a crucial role in the powerful offense that helped Chicago to their World Series title. As general manager of the Red Sox, Epstein drafted Rizzo in 2007. While Rizzo never made it out of the minor leagues with the Red Sox and played fewer than 50 MLB games with the Padres (he was traded to San Diego during the 2010 season), Epstein saw huge potential in him and traded for Rizzo in one of his first moves as an executive. This move worked out extremely well for the Cubs, as Rizzo has won multiple Silver Slugger and Gold Glove awards since his debut in 2012.

Another important component of the Cubs’ 2016 championship run was their large number of young, homegrown players, many of whom were drafted by Epstein. These players included superstars Javier Baez and Kris Bryant, who were important players for the Cubs in 2016. The Cubs drafted Bryant in 2013, and he immediately impacted the offense, winning the NL Rookie of the Year award in 2015 and the NL MVP the following year. Baez had a quieter start in comparison to Bryant after his debut in 2014 but quickly became known for his spectacular defense and his strong offensive performance during the 2016 postseason. Baez has developed into a star offensive player in the last few years, finishing top 3 in the NL MVP race in 2018.

During the years leading up to the 2016 World Series, Epstein also crafted a dominant pitching staff through a variety of trades and signings. In 2013, Epstein traded for pitcher Jake Arrieta, who at the time was a no-name starting pitcher for the Baltimore Orioles. Over the next few years, Arrieta became a superstar for the Cubs, winning the Cy Young award in 2015 and finishing in the top 10 for the award in 2014 and 2016. Epstein effectively found talent through this trade and gave up close to nothing for a pitcher who would eventually become one of the best in the league. During his time with the Cubs, Epstein created an excellent balance between prospects that would help the team in the long term, such as Arrieta, Rizzo, and Baez, and players who provided immediate success. Two players that brought short-term success were starting pitchers Jon Lester and John Lackey, who Epstein signed prior to the 2015 and 2016 seasons, respectively. Both were veterans of the game and provided superb performances on the way to the Cubs’ World Series victory. Lester shined during the 2016 postseason and was a co-winner of the NLCS MVP award while Lackey provided much-needed depth for the starting rotation during their long postseason run.

Though Theo Epstein’s departure from the Cubs organization was not surprising, he frequently said that executives should only be with a team for 10 years — it is certainly a loss for the organization. While the remainder of his career in baseball is up in the air, it is important to recognize him as one of the best MLB executives of this era. Epstein will forever be known as a legend in the cities of Boston and Chicago by breaking not only the Red Sox’ 86-year championship drought but also the Cubs’ 108-year drought. He is truly one of the best in his field.