Due to a very public power struggle with ownership’s Larry Lucchino, the fan favorite resigned and went to Chicago to become the President of Baseball Operations. After breaking the Curse in ’04 with Boston, Epstein struck gold again and directed the Cubs to a World Series title in 2016.
Due to the immense success in Chicago, many fans may wonder what could have been if he had stayed in Boston?
During his tenure in Boston, Epstein oversaw the team win two World Series titles – a ground breaking run in 2004, followed by a domination of the Rockies in 2007.
It was the later part of Theo’s career with the Red Sox that saw both exhibited strugg;es. Theo briefly left the team in the winter of 2005, after a struggle with ownership. Despite the brief hiatus, the young GM returned under a new contract.
Theo is credited with reconstructing the Red Sox farm system by drafting the beloved names of: Jon Lester, Jonathan Papelbon, Kevin Youkilis, Jacoby Ellsbury, Xander Bogaerts, Jackie Bradley Jr and Mookie Betts.
Epstein was a cornerstone and pioneered some huge acquisitions for the Red Sox:
November 2002: Traded four prospects to Arizona for Curt Schilling
December 2003: Signed Free Agent pitcher Keith Foulke
January 2003: Signed Free Agent 1st Baseman / DH David Ortiz
February 15, 2003: Signed Kevin Millar
July 31st, 2004: Acquired Orlando Cabrera, Dave Roberts, and Doug Mientkiewicz while trading away Nomar Garciaparra.
Summer 2004: Selected Dustin Pedroia in 2nd round of draft (65th) overall pick
July 2008: Traded Manny Ramirez to the Dodgers in a three-team deal that saw Boston acquire Jason Bay.
July 2010: Traded for Victor Martinez of the Indians
However, Theo also made mistakes along the way. Who could forget trading away pitcher Bronson Arroyo to the Reds for Wily-Mo- Pena in 2006? Carl Crawford was also a colossal bust.
Overall in his eight seasons as GM of the Red Sox, he was the best of the best, and he has continued his success now with the Cubs.
If Theo had stayed, would we have ever had ever said goodbye to Terry Francona? What about 2012, would we have had Bobby Valentine trade away, Kevin Youkilis? Would we now be under Dave Dombrowski who has acquired big name players such as Craig Kimbrel, Chris Sale in trades, and signed David Price?
While Dombrowski is not Theo, he is a veteran front-office man who’s been around baseball for over 30 years and at one time was the youngest GM in Baseball, when he was the GM of the Montreal Expos in the 1980’s.
Sadly, Dombrowski has piece-by-piece dismantled the farm system pipeline that was once so bountiful under Theo.
As a Red Sox fan, I am forever grateful for the eight years that Theo was here in Boston, and will again be forever grateful for the two World Series titles that the team won.
Red Sox Nation should remain confident that under Dombrowski, as we have seen back-to-back AL East Division titles.
Next step, a World Series ring.