Theo Nathaniel Epstein
After working in the San Diego Padres front office from 1998 to 2002, Theo Epstein was named General Manager of the Boston Red Sox on November 25, 2002. At the time he was the youngest GM in baseball history (Jon Daniels of the Texas Rangers has since surpassed the mark). He famously built the team that ended the Red Sox's World Series drought that dated back to 1918 when the Red Sox won the big prize in 2004, breaking the so-called "Curse of the Bambino". Epstein was identified as one of the key persons behind that victory.
Following a three-year stint with the Red Sox, Epstein and the Red Sox were unable to come an agreement on a new contract following the 2005 season. CEO Larry Lucchino was seen by many as overly meddlesome which may have led Epstein's departure. But within a few months, Epstein returned to his former club in his previous capacity. the Red Sox added another World Series title in 2007. After the 2011 season Epstein asked to be released from his contract as GM. After a long period of negotiation Epstein was allowed to leave the Red Sox and become President of Baseball Operations for the Chicago Cubs. During his time in Boston, ion addition to the two World Series wins, Epstein helped the team make the playoffs six times in ten years.
Epstein's first move in Chicago was to hire Jed Hoyer, who had worked for him in Boston, as the team's new General Manager. That meant that the Cubs would need to pay compensation to Boston for Epstein, and to the San Diego Padres for Hoyer. He then dismissed manager Mike Quade, explaining that he wanted the team to begin with a clean slate. He hired Dale Sveum to be the team's new manager in 2012. On February 21st, the Cubs sent young pitcher Chris Carpenter to the Red Sox in compensation for having hired Epstein while he was still under contract in Boston, and on March 15th added another young pitcher, Aaron Kurcz, to the deal.
While Epstein's goal in Chicago was to finally bring a World Series title to the team's famished fans, in the immediate he proceeded with a complete rebuild, taking advantage of the presence of some good prospects in the team's system. When it came time to hire a manager for the 2014 season, he settled on Rich Renteria, a low-profile candidate whose quality was working with youngsters. Indeed the season saw the trades of some of the last remaining veterans on the team - Jeff Samardzija, Jason Hammel and Nate Schierholtz - while Renteria was given a mandate to play the youngsters. Two younger players with some major league experience, SS Starlin Castro and 1B Anthony Rizzo, formed the core of the new team, with top prospects like Arismendy Alcantara, Javier Baez, Kyle Hendricks and Jorge Soler all making their debuts, and perhaps the best of them, Kris Bryant, waiting in the wings. The Cubs finished last, as expected, and the youngsters found the going hard, but there was promise on the horizon. The plan changed suddenly, however, when long-time Tampa Bay Rays manager Joe Maddon, one of the most respected figures in the majors, suddenly became available in October. Epstein decided to fire Renteria in order to open a spot for Maddon to step into.
The hiring of Maddon turned out to be a genius move. Maddon said that he expected the Cubs to compete immediately, and everyone on the team bought into that. In 2015, the Cubs made the postseason as the second wild card team in the NL - in spite of posting the third-best record in the majors - then beat the Pittsburgh Pirates in the Wild Card Game and upset the heavily-favored St. Louis Cardinals in the NLDS before being swept by the New York Mets in the NLCS. They then came back in 2016 by posting the best record in the majors with 103 wins, and not only did they reach the World Series for the first time since 1945 they defeated the Cleveland Indians, four games to three, in the Fall Classic to clinch their first championship since 1908. He had now shattered the "Curse of the Billy Goat" in Chicago, and was at the helm for two feats that had people taking about him as one the greatest executives in the history of the game - all that while he was still in his early 40s. A few days after the end of the World Series, he was named the winner of the Sporting News Executive of the Year Award.
Contrary to the Red Sox, the Cubs did not add a second World Series title in short order, although they made the postseason in both 2017 and 2018. After a fruitless 2019 season, Maddon left and was replaced by David Ross, one of the players on the championship-winning 2016 team, and the team won another division title in the shortened 2020 season before suffering an early postseason exit. There were now some serious questions about whether the core of the 2016 team was still enough to bring another title to Wrigley, and some hard decisions loomed ahead about whether to rebuild, and how to proceed. Epstein had already said he would not stay beyond 2021, believing any organization needed a new leader after one decade, and on November 17, 2020, he announced he was stepping down earlier than anticipated, giving the reins of the organization to his right-hand man, Hoyer.
|Boston Red Sox General Manager
- Mark Feinsand: "Up next for Theo? 'I need a new challenge'", mlb.com, November 17, 2020. 
- Richard Justice: "With title and award, Epstein feels he 'belongs': Cubs president is Sporting News' 2016 MLB Executive of the Year", mlb.com, November 8, 2016. 
- David Kaplan: The Plan: Epstein, Maddon, and the Audacious Blueprint for a Cubs Dynasty, Triumph Books, Chicago, IL, 2017. ISBN 9781629373263
- Andrew Simon: "Epstein has crafted near-perfect trade record: Under his direction, Cubs built championship team by dealing for major pieces", mlb.com, November 6, 2016.