Does Theo Epstein Regret Leaving the Boston Red Sox?

Jonathan Cullen@@jcullen71Senior Writer INovember 13, 2013

Is Theo wishing that he had stayed in Boston?
Is Theo wishing that he had stayed in Boston?David Banks/Getty Images

After winning the 2013 World Series, the Boston Red Sox celebrated in Fenway Park for the first time in 95 years. As the night unfolded, I wondered if the man who might be most responsible for changing the Red Sox culture and fortunes this century was looking on.

If he was watching, I wondered how Theo Epstein must have felt viewing Red Sox ownership, manager John Farrell and former protege Ben Cherington standing in the middle of Fenway Park receiving the World Series trophy. 

It made me think, does Epstein regret leaving the Red Sox after the 2011 season? 

Epstein left Boston for the Chicago Cubs, taking over the only franchise with a more tormented history than the Red Sox. He was given the title of President and hired his former Red Sox assistant Jed Hoyer as his general manager. 

In the two years that Epstein has been at the helm, the Cubs look to be no closer to a World Series title than when he was hired. Epstein and Hoyer have improved the talent at the major and minor league levels, but the entire NL Central division has improved, making the path to the playoffs that much more difficult. 

It also illustrates that Epstein inherited a Red Sox team that was in far better shape than former general manager Dan Duquette was given credit for at the time. The Red Sox required some tweaks to improve the roster, moves that Epstein deftly made under the microscope in Boston. 

The Cubs were a team with a below-average farm system and devoid of significant talent at the major league level when Epstein took over from former general manager Jim Hendry. Hendry made the classic mistake of trading prospects for a quick fix at the major league level. 

If Theo knew he was looking at a massive overhaul in Chicago, would he have tried harder to resolve his problems with Boston owner John Henry and specifically team president Larry Lucchino? Lucchino and Epstein had a problematic relationship throughout Epstein's tenure as general manager of the Red Sox. 

The Cubs have already had to fire Epstein's first managerial hire, Dale Sveum, after only two seasons in which the team went 127-197. Sveum may not have been the answer, but it has to be alarming that someone that Epstein knew very closely was only given two seasons and cast aside. 

It took Pittsburgh Pirates' general manager Neal Huntington six years to get the Pirates back to .500 and into the playoffs. It is very possible that might be the same time frame Epstein has to follow with the Cubs.

Epstein in recent comments seems to sense that there is growing frustration and concern with the plan that he has put into place with the Cubs. Epstein has total control and if it doesn't work, there will be no confusion on who is calling the shots in Chicago.

For all of the problems that the Red Sox had in 2012, they still had a solid major league core of players including Dustin Pedroia, David Oritz, Jon Lester and Clay Buchholz. In Chicago, there is still a struggle to identify any core players besides Starlin Castro and Anthony Rizzo. 

The Red Sox seemed to have come out the other side after hitting rock bottom as an organization in 2011 and 2012. The collapse at the end of 2011, followed by the exit of Epstein and former manager Terry Francona, led to 2012 and the Bobby Valentine fiasco. These events seemed to be the necessary wake-up call for the entire ownership and management. It forced Boston to change. 

Theo can only hope for the same results in Chicago. The question now is whether Cubs fans will be patient enough to see this all the way through to the end. 

Information used from WikipediaJesse Rogers/ESPN Chicago, Baseball Reference