Comparing Theo Epstein's turnarounds of baseball's two most famously cursed franchises

Just two years after taking over as the Red Sox general manager in 2002, Epstein built a team that won the World Series. After moving to the Cubs in 2011 he needed five years to return to the top. Which accomplishment was more impressive?

The Red Sox took two out of three from the Cubs this past weekend in a Boston series that was more notable for its symbolism—club president Theo Epstein's first visit to Fenway Park since his current team ended its 108-year championship drought—than its outcome. Epstein of course, was the general manager of the Red Sox when they ended their own 86-year dry spell in 2004. The eternal question to ponder is which of the two championships represents his greater accomplishment.

One can make arguments for either of the two, but even so, it's necessary to acknowledge two key points: First, the playoffs are a crapshoot, and both of these teams might be remembered differently had a break or two gone in a different direction. Second, one executive doesn't win a championship any more than one player does. It takes a team, both on the field and off it, to do so.

This actually simplifies an element of the argument, at least for the moment. In Boston, Epstein was the youngest general manager in the game's history at 28 when he was promoted from assistant GM in November 2002. While generally portrayed as the man in charge and credited with masterminding many of the signature moves that helped the Red Sox win it all, at times he clashed with team president/CEO Larry Lucchino. In Chicago, Epstein has more autonomy as the team president with Jed Hoyer, a former assistant in Boston, the GM. But for the purposes of this this discussion, we can set the distinction aside.

Building the Red Sox

Owner John Henry, who had purchased the team in early 2002, decided that he wanted to take a page from the upstart Oakland A's by using analytics to build a better ballclub. Only after failing to woo A's GM Billy Beane and then former Beane assistant J.P. Ricciardi, by then the GM in Toronto, to spearhead what would later be described as a "Moneyball with money" strategy did he turn to the analytically-inclined Epstein.

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Epstein took over a team that had finished second in the AL East for five consecutive years, including wild-card berths in 1998 and ’99, and was coming off a 93-win season in 2002. As good as Boston was, it had spent most of that period having sand kicked in its face by the rival Yankees, who were in the midst of a period in which they won six division titles, five pennants and four World Series championships from 1996 to 2002.

The Sox squad Epstein inherited was not hurting for talent. Starting pitchers Pedro Martinez and Derek Lowe had finished 1–2 in the AL In ERA in 2002 and were two of Boston’s six All-Stars, having been joined by shortstop Nomar Garciaparra, third baseman Shea Hillenbrand, centerfielder Johnny Damon and leftfielder Manny Ramirez. Solid contributors such as catcher Jason Varitek, outfielder Trot Nixon and pitcher Tim Wakefield were on the roster as well. The team did need some work, as DH/first baseman Brian Daubach, outfielder Cliff Floyd (a midseason acquisition) and All-Star closer Ugueth Urbina all reached free agency.

Epstein (and his colleagues) showed great creativity in filling those holes. Casting a wide net to fill the first base/DH slots, he signed David Ortiz, who had been non-tendered by the Twins, traded for Jeremy Giambi and purchased Kevin Millar from the Marlins by disrupting the common transaction protocol—the passing of a player through waivers before he's sold to a Japanese team—with a waiver claim that literally created an international incident. Giambi didn't pan out, but Millar hit 25 home runs and drove in 96 runs and Ortiz proved to be one of the most fortuitous signings in baseball history. Another free agent signing, third baseman Bill Mueller, won the AL batting title in 2003, and a trade with the Reds netted starting second baseman Todd Walker (.283, 85 RBIs). The bullpen situation wasn't solved as neatly, as a closer-by-committee attempt involving free agents Mike Timlin, Ramiro Mendoza and others created a mess that wasn't really solved until Hillenbrand was traded to the Diamondbacks in late May for Byung-Hyun Kim. The 2003 Red Sox won 95 games, their highest total since 1986, but lost to the Yankees in a classic seven game ALCS that ended on Aaron Boone’s home run off Wakefield.

That loss cost manager Grady Little his job, and Epstein took a chance by hiring Terry Francona, who had posted four losing seasons in Philadelphia but who had spent the ’03 season as the bench coach in Oakland, where he was exposed to the usage of analytics in running a team. That November, Epstein made a trade with the Diamondbacks to acquire ace Curt Schilling and would soon attempt another blockbuster to acquire Rangers shortstop Alex Rodriguez; that deal, which would have sent Ramirez and pitching prospect Jon Lester to Texas and Garciaparra to the White Sox, fell through over the attempts to restructure A-Rod's contract. Epstein did sign free agent Keith Foulke, the 2003 AL saves leader, to be the closer and dealt for the Rockies’ Mark Bellhorn to replace Walker, who had signed with the Cubs, at second base.

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All that maneuvering helped Boston win 98 games, its most since 1978 but still three games short of the 101-win Yankees. That July, Epstein pulled off one more masterstroke, completing a four-team trade with the Cubs, Expos and Twins that sent the gimpy and sullen Garciaparra to Chicago and brought back shortstop Orlando Cabrera from Montreal and first baseman Doug Mientkiewicz from Minnesota. The moves shored up the defense, and the Sox played .700 ball after the trade. They swept the Angels in the Division Series, came back from a three-games-to-none deficit in the ALCS to vanquish the Yankees and then steamrolled the Cardinals in the World Series to claim their first championship since 1918. Boston would make the playoffs four more times over Epstein’s final seven seasons in charge, including a second world championship in 2007.

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Building the Cubs

After the Red Sox collapsed in 2011 and missed the postseason, Epstein left his hometown and took over another long-suffering franchise. The Cubs had been NL Central champions in both 2007 and ‘08, but were coming off consecutive losing seasons and owner Tom Ricketts, who had purchased the team in 2009, was eager for a change in direction. He fired GM Jim Hendry in July 2011, and three months later brought in Epstein as the team's president of baseball operations, with Jed Hoyer and Padres assistant GM Jason McCloud, also a former Boston assistant, joining him as GM and director of scouting, respectively.

Unlike in Boston, where a full rebuild was not required, Eptein and Co. had to try and construct a championship roster from the ground up. He let productive but expensive hitters Carlos Peña and Aramis Ramirez depart after the 2011 season, dealt righthander Carlos Zambrano to the Marlins and traded 2008 first-round pick Andrew Cashner to the Padres in a deal that brought back Anthony Rizzo to be the team's starting first baseman. In July 2012 Epstein traded ace Ryan Dempster to the Rangers for a package that included minor league pitcher Kyle Hendricks. The Cubs dropped 101 games in 2012, their highest total since 1966, and 96 games in ’13, but all that losing that gave them top-five draft picks that they used to select Kris Bryant (No. 2, 2013) and Kyle Schwarber (No. 4, ’14).

A couple of Epstein's trades in July 2013 also wound up paying significant dividends. First he sent swingman Scott Feldman and backup catcher Steve Clevenger to the Orioles in exchange for righthander Jake Arrieta, a former top prospect who had yet to pan out, and hard-throwing reliever Pedro Strop. Three weeks later he dealt righty Matt Garza to the Rangers in exchange for pitchers Carl Edwards Jr. and Justin Grimm. The pricey Carlos Marmol and Alfonso Soriano were also unloaded that summer, with considerable salary absorbed.

In 2014 the Cubs improved to 73 wins, with Rizzo earning All-Star honors for the first time and Arrieta posting a 2.53 ERA, but the focus remained upon laying the long-term groundwork. In July, pitchers Jeff Samardzija and Jason Hammel were traded to the A's in a deal that brought back shortstop prospect Addison Russell.

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After the 2014 season, Epstein changed directions by adding veterans to his nucleus. He acquired catcher Miguel Montero from the Diamondbacks and signed Lester, Hammel and catcher David Ross as free agents. In January, he dealt pitcher Dan Straily and infielder Luis Valbuena to the Astros for centerfielder Dexter Fowler. And, perhaps most significantly, he hired Joe Maddon to be his manager when the Rays skipper unexpectedly became available due to an opt-out clause in his contract.

In 2015, Bryant, Russell and Schwarber all made their debuts, Arrieta won the NL Cy Young Award and Chicago vaulted to 97 wins and a wild card berth. The Cubs beat a pair of division rivals, the 98-win Pirates and the 100-win Cardinals, to reach the NLCS before being swept by the Mets.

With the December 2015 trade of second baseman Starlin Castro to the Yankees, the emergence of longtime prospect Javier Baez (one of the few holdovers from the Hendry regime), the additions of free agents Jason Heyward, John Lackey and Ben Zobrist and the surprise retention of Fowler after he appeared bound for the Orioles, the 2016 Cubs were a juggernaut. They won 47 of their first 67 games before coasting to the NL Central crown with a 103-58 record. Even with a huge midsummer lead, Epstein bolstered his team’s bullpen by acquiring closer Aroldis Chapman and set-up man Mike Montgomery around the trade deadline. In the postseason Chicago knocked off the Giants, Dodgers and Indians—the last of those in an extra-innings Game 7 thriller—to win their first world championship since 1908.

The Verdict

As the executive most closely identified with both the 2004 Red Sox and the 2016 Cubs, Epstein has likely guaranteed himself a spot in the Baseball Hall of Fame. In both cases, his signature moves—including hiring the right managers—paid great dividends and figured significantly in ending those droughts. In Boston, he did it by overhauling a contender on the fly; the 2004 club had just seven principal contributors who had been in place two years earlier (Damon, Lowe, Martinez, Nixon, Ramirez, Varitek and Wakefield). In the fishbowl environment that is Boston sports, the revamped team had to chase away talk of the "Curse of the Bambino" as well as actually getting past a powerhouse Yankees squad. And they had to do it all while carrying the banner for the prominent use of analytics in front office decision making, because few other teams were doing so in an industry polarized by Michael Lewis’ 2003 book.

That's a tremendous accomplishment, but it takes a back seat to the unfolding of the five-year plan in Chicago. Epstein and his regime made shrewd trades, drafted smartly and hit the jackpot on several free-agent acquisitions, going from 101 losses to 103 wins in just four seasons.

Still, while the Cubs are well-positioned to continue contending with this nucleus, Epstein's total body of work in Boston is still the greater one—at least for now. He put his stamp on that 2007 title squad with post-‘02 draft picks Dustin Pedroia and Jonathan Papelbon as well as trade acquisitions Josh Beckett and Mike Lowell. Those Sox nearly made it back to the World Series the following year, losing a nail-biting seven-game ALCS to Maddon’s Rays, and they averaged 91.3 wins over Epstein’s final three years in Boston.

So call it a split decision: The 2016 championship was a more impressive building job, but Epstein’s full run in Boston has, for now, yielded more success. The final verdict won’t be known for a few more years, because we surely haven’t heard the last of these Cubs.