At 46 years of age, Theo Epstein's legacy in baseball is secure. As the chief architect of teams that ended a combined 194 years worth of World Series title droughts, Epstein will always be in the conversation of baseball's all-time great executives. He is arguably the most successful executive in the history of both the Boston Red Sox and the Chicago Cubs, two of the flagship franchises in baseball, teams that play their games in the two most storied venues in the game.
That, really, is the summation of where Epstein stands on the day news came that he is stepping down as Cubs president of baseball operations.
It's hard not to think back nine years ago, when Epstein left the Red Sox and, shortly after, joined the Cubs. He left the Red Sox in a better place than he found it, though he did not get the ball rolling in Boston. That credit goes to Epstein's mentor, Larry Lucchino. But it was Epstein who carried it across the finish line, winning two titles in 10 years as the Red Sox became an economic and on-the-field powerhouse.
The challenge in Chicago was different for Epstein. When he took over baseball operations for the club on Oct. 12, 2011, the Cubs were in a bad place. The payroll was bloated. The minor-league pipeline was sputtering. And to say that Chicago's baseball processes were behind the times would be a massive understatement.
Everything in Wrigleyville looks different than when Cubs co-owner Tom Ricketts turned his club over to Epstein. The team's operations have been modernized and continue to evolve. The ballpark has been renovated, as has most of the property surrounding Wrigley Field. While the Ricketts family has been the primary driver of those things, the success the Cubs enjoyed under Epstein and his staff has helped pave the way.
Now that Epstein has walked away with one year remaining on his contract, it's fair to make the dual observation that his tenure was both the most successful in franchise history from an executive standpoint but also one in which it feels like there was some money left on the table.
That's not exactly a criticism of Epstein, who in a way is in the same boat as future Hall of Fame executives Billy Beane and Andrew Friedman as being victims of their own success. Those with whom they have collaborated over the years take jobs with other teams and carry with them the progressive ideas for running a team, which then are iterated into even newer innovations, and the competitive landscape grows ever more challenging with each season. Uncovering innovations that lead to on-field success has never been more challenging for a baseball executive.
Epstein has always been someone who seeks the freshness of a new challenge and his departure on Tuesday had been signaled since the end of the 2020 season, when there was no indication that he sought to extend his time with the Cubs beyond 2021. Indeed, he has always maintained that 10 years is long enough for one person's voice to be the dominant one in a baseball organization. The plan now is to turn the job over to Cubs GM Jed Hoyer, with whom he has worked for 17 of the last 19 years from San Diego to Boston to Chicago.
That Epstein made the move a year early is a mild surprise until you consider his relationship with Hoyer. If Hoyer is going to be charting the course for the Cubs, then why not empower him now, when so many key decisions have to be made?
"The organization faces a number of decisions this winter that carry long-term consequences," Epstein stated via the Cubs' announcement of the news. "Those types of decisions are best made by someone who will be here for a long period rather than just one more year. Jed has earned this opportunity and is absolutely the right person to take over this baseball operation at such an important time."
Among the key decisions are whether to extend star shortstop Javier Baez, who can become a free agent after next season. There is the perennial question of whether to trade or extend franchise cornerstone Kris Bryant. Anthony Rizzo and Kyle Schwarber, other key parts of the Cubs' offensive core, are also one year from hitting the market.
This is all happening at a time when the pandemic has sucker punched baseball's revenue streams, and it's come at a particularly bad time for the Ricketts family, who oversaw the ballpark renovations as well as many of the developments surrounding the venue, and launched a Cubs-centric sports network. All of this was meant to turn the Cubs into one of baseball's top economic juggernauts and, eventually, that's probably going to happen. But for now, so much is mired in limbo.
Now it will be up to Hoyer and the Cubs' revamped front office to navigate that limbo. Among his key lieutenants will be Jason McLeod, the Cubs' senior vice president of player personnel, who was reportedly a finalist for the Angels' GM opening, which was filled with the hiring of former Braves executive Perry Minasian. Also, vice president of scouting Dan Kantrovitz reportedly declined a chance to interview for the Angels' job and could be given more responsibility. Even without Epstein, the Cubs' brain trust will have both industry respect and much-needed continuity.
As for Epstein, his next move appears to be simply to take a step back and enjoy a year off. According to ESPN's Jeff Passan, in a letter to friends and colleagues explaining his decision, Epstein wrote: "I do plan on having a third chapter leading a baseball organization someday, though I do not expect it to be next year."
This is, of course, bad news for the New York Mets and Philadelphia Phillies, two big-market teams looking for general managers. Maybe they could gamble by making an interim hire and go about wooing Epstein in the meantime, or go with a committee approach, but either move would indeed be a gamble. With Epstein a free-agent executive, even if the Mets and Phillies declined to hire a permanent GM for the time being, there will be even more competition for Epstein's services as time passes. One carrot that owners will probably need to dangle was suggested by another snippet from Epstein's letter: "If and when the timing and opportunity and partners are right, I would like to join an ownership group."
From now until the time that Epstein takes his next job, one of the most intriguing questions in baseball will be this: For whom will Epstein's third chapter be written?
First things first, as Epstein isn't quite through. He is finishing off his Cubs tenure, with his last day coming this Friday, and that makes this a time to look back. That tenure will have included nine seasons. The first three were rebuilding campaigns, as Epstein and Hoyer oversaw a tear-down-to-the-studs overhaul of the organization. The pain proved to be worth it.
The last six seasons saw the Cubs enjoy their longest sustained stretch of success since the Great Depression. Long-suffering Cubs fans have basked in six straight winning seasons, culminating in three division titles, five playoff appearances and the drought-snapping 2016 World Series title. The transition from what the Cubs were to what the Cubs have become is remarkable.
Nevertheless, Epstein's tenure in Chicago wasn't perfect. There was the eight-year, $184 million free-agent contract to Jason Heyward, who has helped the Cubs win but has generally not produced at the level demanded by that investment. Heyward still has three years remaining on that deal. There was some prospects-for-a-veteran deals that don't look great in retrospect, particularly the trade that sent Eloy Jimenez and Dylan Cease to the crosstown White Sox for Jose Quintana.
From a wider lens, there was the early decision in the rebuild to go heavy on the development of position players, with the hope being the pitching staff could be filled out via free agency. That worked in the case of Jon Lester, but the almost complete lack of organizationally-developed pitchers has hampered the Cubs from both a depth standpoint and in terms of being able to make impactful trades. Also, the star-studded group of young position players who helped the Cubs to the title seemed to plateau in their collective development, as the offense fell short of expectations again and again.
All of this, along with the rise of the Dodgers and some plain old bad postseason luck, conspired to limit this historic version of the Cubs to that one unforgettable championship, rather than seeing them be the dynasty that they once seemed destined to become.
Still, just as was the case in Boston, you can make the very simple observation that Epstein is leaving the Cubs in much better shape than he found them. Despite the hope, even the expectation, that there would be more than one title -- an expectation that Epstein's success was largely responsible for creating -- he leaves the organization knowing that the mission he set upon just over nine years ago was accomplished. And it was the most daunting mission in sports: helping the Cubs end more than a century of championship futility.
He did that and in doing so, the former boy wonder from New England became a Windy City institution.