Theo Epstein to Chicago Cubs: Why This Is an Even Harder Test Than the Red Sox

Matthew Dicker@@MattDickerContributor IIIOctober 14, 2011

BOSTON - NOVEMBER 2:  Theo Epstein speaks to the press about his resignation as the general manager of the Boston Red Sox November 2, 2005 at Fenway Park in Boston, Massachusetts. Epstein resigned on October 31 nearly a year after the franchise won its first World Series championship since 1918.  (Photo by Darren McCollester/Getty Images)
Darren McCollester/Getty Images

Theo Epstein came into Boston as the handpicked protégé of new owner John Henry and built the Red Sox into World Series champions, putting to rest once and for all the famed Curse of the Bambino. 

Such is the narrative of Theo Epstein that has become part of Boston Red Sox lore. 

Now that he is headed to Wrigleyville to wage war against an even greater curse, Cubs fans are salivating at the thought that Epstein can bring a World Series to Chicago’s north side for the first time since Teddy Roosevelt’s presidency.

Cubs fans would be wise, however, to hold off on stocking up on champagne. Though Epstein’s hiring gives fans more hope than anything else has in years, he has his hands full in turning the Cubs into championship contenders.

When Epstein inherited the Red Sox, they were a good team that needed the finishing touches to make them a championship team; the Cubs are a team 11 games short of .500 and in need of a complete redesign.

The 2002 Red Sox: Better Than Advertised

Theo Epstein has earned praise both for bringing proven talent to the Red Sox, such as Curt Schilling, and finding hidden talent in the previously overlooked, such as David Ortiz. While Epstein’s acquisitions were critical to the success that followed, the team he inherited was already stocked with talent, boasting some of the finest players in the game.

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The roster included Hall of Fame-caliber talent like Pedro Martinez and Manny Ramirez; stars like Tim Wakefield, Derek Lowe, Nomar Garciaparra and Johnny Damon; and future team leaders like Trot Nixon and Jason Varitek. The Red Sox had been successful as a team as well, and were coming off a season in which they had won 93 games, 11 more than the previous season when Epstein took the big office. 

CHICAGO, IL - SEPTEMBER 21: Reed Johnson #5 of the Chicago Cubs watches as his son Tyce slides into home plate after the Chicago Cubs Milwaukee Brewers game on September 21, 2011 at Wrigley Field in Chicago, Illinois. The Cubs defeated the Brewers 7-1.  (
David Banks/Getty Images

The Cubs, by contrast, have no such wealth of talent.

The team is coming off a 71-91 season, 22 wins less than the Sox team Epstein inherited. The 2011 season was no fluke; in each of the last three seasons, the Cubs have decreased their win total. The Cubs boast no future Hall of Famers, and their biggest offensive star likely to remain on the team, Alfonso Soriano, hit only .244 in 2011 and will be 36 years old next season.

Though the Cubs have some excellent young talent, notably Starlin Castro, they are nowhere near the level of the 2002 Red Sox.

The Cubs' bright spot is their pitching staff. Matt Garza has been a welcome addition to the staff, Ryan Dempster is an innings-eater extraordinaire and Carlos Zambrano still has moments of brilliance. Still, the staff is a long way off of Pedro Martinez, Derek Lowe, John Burkett and Tim Wakefield. 

Challenging Finances

Every new general manager inherits a few contracts he wishes he could void, and Epstein is no exception. He inherits a $14 million contract for Ryan Dempster, who struggled with a 4.80 ERA and a 10-14 record last year, and $6.5 million for Marlon Byrd. Most difficult for Epstein to navigate around will be the $18 million each owed to Alfonso Soriano and Carlos Zambrano. 

Epstein also has to deal with a much smaller payroll than he grew accustomed to in Boston.  While owner Tom Ricketts has not publicly announced what his expected payroll for 2011 will be, he has said that he expects the entire baseball operations budget to remain near what it was in 2011; thus, it is unlikely that the payroll will increase dramatically from the $126 million spent in 2011. 

Epstein was able to spend $160 million in Boston in 2011, meaning he has over 20 percent less money to spend than he did last season. 

BOSTON - APRIL 12:  Executive Vice President and General Manager Theo Epstein of the Boston Red Sox looks on before their game against the Toronto Blue Jays on April 12, 2006 at Fenway Park in Boston, Massachusetts.  (Photo by Jim McIsaac/Getty Images)
Jim McIsaac/Getty Images

Lack of Depth in Minor Leagues

Epstein is unlikely to get much help from the Cubs' young talent. The team’s farm system was ranked 14th of 30 by Baseball America last week. The Cubs have also struggled to develop offensive talent internally in recent years. Of the team’s 10 leaders in at-bats in 2011, only three began their career with the Cubs.

They have been more successful in developing their bullpen, but the Cubs lack potential superstars in their minor leagues. While the Red Sox team he took over were already contenders only a few pieces away from a championship-caliber team, Epstein will have to decide early whether he wants to focus on building the Cubs' farm system or look elsewhere for talent.

No Longer the Only Show in Town

When Theo Epstein became GM of the Red Sox, he was a part of the small cadre of young baseball executives who were looking at baseball differently than their predecessors. Epstein was one of the first of the young turks to take the helm of a team, and his approach to building a team, coupled with the Red Sox's generous resources, allowed him to take advantage of the leagues’ inefficiencies.

Nine years later, the rest of the league has caught up, and the members of the Moneyball Generation fill the ranks of Major League front offices. Just as Billy Beane has struggled to maintain his edge over opponents who have embraced his philosophy, Epstein now must contend with those who share his approach to the game. 


The Cubs have spent years in the baseball wilderness, not due to any curse, but instead due to poor management that was unwilling to design a strategy and stick with it over the long haul. 

Owner Tom Ricketts has made a wise move in bringing in top talent at the general manager position, and if he gives the resources for Epstein to run the team effectively, there’s no reason the Cubs can’t improve beyond their current state—it would be hard to get much worse.

Theo Epstein surely is salivating at the challenge of delivering two star-crossed teams from their miserable fates, and he would write his ticket to the Hall of Fame if he could bring a World Series trophy to Wrigley. But while he deserves a great deal of credit for building the team that won two World Series in Boston, he was granted a large head start that he will not have in Chicago.

If Epstein can turn the Cubs into a championship contender, he will truly be the best general manager in baseball.