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What Will Be Epstein’s Third Act?

Baseball wunderkind Theo Epstein is leaving the Chicago Cubs. Here’s where he might take his talents next.

Theo Epstein by APardavila is licensed under CC BY 2.0

What Will Be Epstein’s Third Act?


Estimated Reading Time: 4 Minutes

Baseball wunderkind Theo Epstein has broken the two biggest curses in Major League Baseball history, but next season will be his first in 30 years not working at a ballpark.

Epstein announced Tuesday that, with his contract with the Cubs set to expire after the 2021 season, he will step down as the President of Baseball Operations in Chicago a year early.

As part of the announcement, Epstein noted that he does “plan on having a third chapter leading a baseball organization someday…”

So where will Epstein land in a year or two for his third act? If he wants to continue his trend of helping long-suffering franchises taste World Series victories, he may well end up staying in middle America.

Here are the teams with the biggest World Series title droughts, who could benefit from Epstein’s magic touch.



Cleveland Indians

Drought: 72 Years
Last World Series Won: 1948
Last World Series Appearance: 2016

Epstein is well acquainted with the Cleveland Indians World Series agonies, which include losses in 1954, 1995 and 1997, but particularly with the 2016 Fall Classic.

That thrilling series pitted two of the longest droughts in MLB history, with Cleveland against Epstein’s Cubs. The Indians were on the verge of coming off of the list of droughts and continuing the Curse of the Billy Goat when they took a 3-1 series lead, but the Cubs came back to tie the series, then won it in extra innings even after Rajai Davis hit a dramatic two-run homer to keep Cleveland alive with two outs in the eighth.

A stint in Cleveland would be a natural fit for Epstein, who would reunite with manager Terry Francona, the skipper that he teamed with in Boston when the Red Sox broke their own curse in 2004.


Texas Rangers

Drought: 60 Years
Last World Series Won: Never
Last World Series Appearance: 2011

Though the Rangers’ drought is not quite as long as that of Boston or Chicago, Texas fans might lay claim to some of the worst suffering in recent history after they came inches away from beating St. Louis in six games in 2011.

The Rangers one strike away from their first ever championship, but Nelson Cruz famously drifted back lazily on a fly ball by David Freese which got over his head for a game-tying two-run triple. Freese later hit a walk-off homer in the bottom of the 11th to force a Game 7, then knocked in two runs in Game 7 on the way to being named World Series MVP.


Milwaukee Brewers

Drought: 52 Years
Last World Series Won: Never
Last World Series Appearance: 1982

The Brewers, an American League East team until 1998, made their only appearance in the World Series in the 1982 “Suds Series” against the St. Louis Cardinals, home of Anheuser-Bush, commercial rivals to Miller Brewing, based in Milwaukee. Milwaukee took a 3-2 series lead with wins in Games 4 & 5 at County Stadium, but were pasted by the Cardinals 13-1 in Game 6 which, despite 14 runs scored, was the shortest game of the series at 2 hours and 21 minutes.

Milwaukee has not been back to the ship since then, but have been in the playoffs each of the last three years, including an NL Central crown in 2018.


San Diego Padres

Drought: 52 Years
Last World Series Won: Never
Last World Series Appearance: 1998

Like the Brewers, it has been more than two decades since the Padres have been in the World Series, and the last time they were there it went…not so well.

After home plate umpire Rich Garcia failed to ring up Tino Martinez in the seventh inning of Game 1 and Martinez hit the next pitch for a grand slam to overcome a three-run Padres lead, the Yankees dominated the 1998 World Series to win their 24th title.

The Padres have been in the playoffs just three times since then and have not gotten out of the Divisional Round. This year’s team, after breaking a 14-year playoff drought, were swept in three straight days by the Los Angeles Dodgers.

So Where will Epstein end up? Will he deliver one of these suffering fan bases a World Series title like he did with the Red Sox and the Cubs? Will he take his talents to another part of the country? Or, assured of his spot in the Hall of Fame, will he step away from the game and focus on his foundation, the Foundation to be Named Later?

Craig has spent the last ten years as a sports information professional, working for several schools across New England at the Division 3 level. A native of Peabody, Mass., Craig is a life-long Boston sports fan. He is also an avid player of fantasy football and baseball, and commissioner of the AKA Family Fantasy Football League. Like most other Turf team members, Craig has a penchant for theater, spending his high school and college years as a set designer, sound designer and theater shop worker. He became a father shortly before the coronavirus pandemic, and as such, hasn't really left his home since last December.

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