Theo Epstein: Boston Red Sox GM Should Take His Talents to Chicago Cubs

For the last nine years, Theo Epstein has run the Red Sox with Moneyball statistical analysis and a payroll second only to the New York Yankees.

His tenure includes two World Series rings in 2004 and 2007, but a change of scenery might be beneficial for both parties after missing the playoffs two out of the last three years.

With the high-budget Chicago Cubs in need of a new General Manager and his Red Sox in revolt, here are some factors that may influence Theo’s next employment contract.

Job Security

Many GMs have World Series credentials; some even have multiple rings, but there is only one man credited with ending the 86-year Curse of the Bambino in 2004.

Theo’s major move that year was to trade franchise shortstop Nomar Garciaparra for two utility-level players, Orlando Cabrera and Doug Mientkiewicz—a decision that would have been roundly panned had it not worked perfectly. The 2004 outcome and 2007 reminder kept Theo in the good graces of Red Sox fans until the 2011 team underwhelmed every performance expectation.

Theo must now leave the AL East for a fresh start and the job security that comes with it.

Roster Turnover

If you were a GM, would you rather dump bloated contracts from your existing team or clear the fodder from a new one?

Theo can stick around Boston to reshape a pitching staff beset by the contracts to Daisuke Matsuzaka and John Lackey or he can go to Chicago and avoid final responsibility for these disastrous deals.

Is it better for your reputation to stress about another six years of Carl Crawford (for $20 million apiece) or to go to Chicago, where signing Alfonso Soriano wasn’t your fault?

Theo may be a better GM for the Cubs, as he won’t feel undue loyalty to bad contacts and will have a clear mind to retool the roster.  

Legacy

Theo will always be known for changing the expectations in Boston after his 2004 success but this will matter more to historians than the Boston faithful should another terrible season follow the 2011 collapse.

If he were to land in Chicago and have similar success for the longest-standing championship drought in American sports, well…a first-ballot Hall of Fame induction is only the beginning.

Despite the salary JD Drew collected for the last few years, Theo could be considered the best GM of his generation.

Ultimately, the ceiling is lower in Boston than it could be in Chicago and you have to expect a man with his ambition to become the youngest GM in baseball history to reach for the eternal glory of a Cubs World Series victory.

Odds to leave for Chicago: 75%