It’s easy to compare the Chicago Cubs to the Boston Red Sox. It’s almost too easy because of how long both teams went without winning it all, but the Cubbies won the 2016 World Series with enough former Red Sox personnel that it would be borderline-irresponsible not to at this point.
This year’s disappointing end to Chicago’s season was a particularly dramatic collapse. The Cubs were in control of the NL Central for most of the season, and were widely considered the National League’s best team for much of it. But the Milwaukee Brewers were not content with merely clinching a postseason berth, got hot down the stretch, and caught the Cubs after 162 games. In Game 163, the Brew Crew completed their transformation from plucky, happy-to-be-there young Wild Card hopeful to the top team in the National League, with home field advantage in both the Divisional and League Championship series.
The Cubs, of course, lived to play another day, but in the Wild Card Game, they lost at Wrigley Field in 13 innings to the Colorado Rockies, who themselves were the losers of a Game 163 with the Los Angeles Dodgers. A month ago, the Cubs were regarded as the best team of the bunch that ended up having to play an extra regular season game, but their season ended the soonest.
I cannot help but think of the ways in which the Red Sox have let me down since 2004 when I look at this Cubs team. You don’t even have to go back to 1978 and Bucky Dent for demoralizing defeats this time of year. The 2011 Red Sox, the infamous “Fried Chicken and Beer” squad is there for that. Like the 2018 Cubs, Jon Lester was in that rotation and had already won a World Series for his current team. Terry Francona lost his job in Boston after that collapse, and I know there are fans in Chicago calling for Joe Maddon to be fired today. My question today, however, is “at what point are we in Theo Epstein’s employment cycle?”
At 29, Theo Epstein was the youngest general manager in MLB history (and the youngest in any of the four major sports until the Arizona Coyotes hired 26 year old John Chayka a couple years ago) when the Red Sox promoted him. He was a Massachusetts native who inherited a pretty good roster, but made the moves necessary to put the team over the top, winning the World Series in 2004.
In 2005, the Red Sox managed the World Series hangover rather respectably, clinching a Wild Card berth yet again, but getting swept in the ALDS by the eventual champion Chicago White Sox. That offseason, Epstein announced he was leaving the team, and left Fenway Park in a gorilla suit. He was back with the team by the start of the 2006 season, having won his power struggle with team president Larry Lucchino, but I thought even then that it was only a matter of time before Epstein leaves for another team and another challange. Once you’ve won a World Series in Boston, what else is there to do?
The Red Sox won another one in 2007, but it would not have happened the way it did without a trade that happened when Epstein was not with the Red Sox. Josh Beckett was the team’s best pitcher that year and Mike Lowell was the World Series MVP, and they came to Boston in a trade that sent Hanley Ramirez to the Florida Marlins. That wasn’t Epstein’s trade.
Four years of increasingly diminishing returns following the 2007 title culminated with the Red Sox’ worst collapse since 1978. They did not even get to a Game 163 because they choked away the final game against the Baltimore Orioles. That team was the first time the Red Sox felt like the Red Sox again for the first time since 2004, in all the worst ways. While the Red Sox would turn things around and win the World Series again in 2013, they would do so without Epstein, who left after the 2011 collapse to rebuilt the Cubs.
While Brian Cashman has won more titles in his years running the New York Yankees, and Billy Beane may have been played by Brad Pitt in an Academy Award-nominated movie for his work running the Oakland Athletics with limited resources, but Theo Epstein cemented his legacy as the greatest baseball executive of his generation in 2016 when he guided the Cubs to their first tile since 1908. He has won three World Series with two of the most famously tortured franchises in all of professional sports, and he is still only 44.
Epstein has a chance to be the most important and influential GM in MLB since Branch Rickey. Rickey, who was played by a delightfully grumpy Harrison Ford in 42, had a career that stretched from 1913 to 1955 with the St. Louis Browns, St. Louis Cardinals, Brooklyn Dodgers, and Pittsburgh Pirates, Rickey won four World Series titles with the Cardinals, but laid the groundwork for eventual champs in Brooklyn and Pittsburgh. Along the way, he developed the farm system and broke baseball’s color barrier by signing Jackie Robinson (and if you ever have plenty of time to kill, you should check out his scouting reports archived on the Library of Congress’ website). Rickey had a good thing going in St. Louis, but increased the importance of his legacy by taking on the challenges in Brooklyn and Pittsburgh. Winning in Boston was not enough for Theo. Winning in Chicago might not be enough for him, either. Perhaps the San Diego Padres, where Epstein’s front office career began, and a city that has never won a World Series, could be the next challenge for him to conquer. San Diego also wouldn’t be the worst place in the world to live.
At the end of the day, the Cubs still have a solid foundation for a competitive baseball team, but the honeymoon is over after the thing that was never going to happen happened in 2016. It’s disappointing, Cubs fans, but it can’t hurt as bad as it did before. It’s all part of the change of identity that fans have to reconcile with once they win. Baseball was never going to just stop for the Cubs, or the Astros, or the Red Sox. But the sympathy from the fans who have not won as recently will never be as sincere as it was before. And while Theo is likely to stay the course for the time being, I would not be shocked if he left Wrigley in a gorilla suit one of these years.