Theo Epstein: The Cubs Messiah?

When the Chicago Cubs relieved Vice President/GM Jim Hendry of his duties on August 19, 2011 the rumor mill began swirling hard and fast. All across America (and Canada don’t worry we see you up there Alex Anthopoulos) GM’s and their many assistants turned their heads to focus in on the developing situation at Wrigley Field. With the Red Sox toppling the mighty Yankees and putting Babe Ruth’s ghost to rest by winning a World Series in 2004 (they threw in one in 2007 just for fun) the Cubs now stand alone as baseball’s longest losers. The Cubbies have become known as the “Loveable Losers” a fun nickname but not one you want hanging over your franchise. After another year under .500 in 2011 the drought now sits at 103 years with no end in sight.

The Cubs have money (they checked in at $126.4 million ranking 6^th in all of baseball in 2011), a new ownership group led by the Ricketts family, and the allure of becoming a man, a myth, and a legend for bringing a winner to Wrigley. The Cubs job has attracted connections to many of the biggest names in baseball. Billy Beane, Brian Cashman, and (a loud gulp from Red Sox Nation) Theo Epstein have been linked as possible candidates to take over the Cubs. The possibility of Theo Epstein leaving the friendly confines of Fenway for the view from 1060 West Addison Street, Chicago Il is dumbfounding to most members of the Nation but it’s not as far fetched as one might think. Many of you are asking why would Theo leave a team with the magnitude of resources as the Boston Red Sox have for the dreary forecast of Chicago wind? Quickly followed up by the question of what would the Red Sox next move be?

Let’s answer the first question here of why Theo would even consider heading to Chicago to take over the Cubs organization. When he first took over as GM of the Red Sox in late 2002 they were sitting on a 84 year drought while playing in a division with the mighty Yankees. The Red Sox job was the ‘it’ job (right Billy Beane? Wait, you accepted then reneged) while the challenge was daunting and to the man who could conquer the demons of almost a century of losing would go the spoils. He would be revered as a savior in a city where the Red Sox will always reign supreme. In only his second year on the job Theo did just that putting together a conglomeration of players that exorcised the demons and swept the overmatched St. Louis Cardinals in 4 games. Theo had done it, the challenge had been completed though for good measure he thrown in another title in 2007 (again sweeping the over rested Colorado Rockies). In between however Theo resigned after the 2005 season due to a rift with President and CEO Larry Lucchino (see: exiting the building in a gorilla suit). On the outside the two men claim that their relationship has never been better but underneath the public love affair there is zero chance the animosity has left the building. You’re now asking yourself ok if Theo hates Lucchino so much why has he stayed around this long? Let me explain my dear reader why he has stayed around and what makes the Cubs job so enticing to a man like Theo Epstein.

Outside of Lucchino, Epstein has a great working relationship with principal owner John Henry and manager Terry Francona. Francona and Epstein have teamed up to win 2 World Series titles in a 9-year span. His resources in Boston seem to be unlimited and unable to matched by any organization this side of the Evil Empire but not so fast. The Ricketts family since taking over the role as principal owners has promised to spend on talent to upgrade the roster. The promise of spending might be fulfilled this winter if the Cubs go after SP C.J. Wilson from Texas and either Albert Pujols or Prince Fielder. The team also has talent on the big league roster in Matt Garza (hate that spitting habit), Starlin Castro (hey, batters this way, pay attention!), Carlos Marmol, and Jeff Samardzija (kid should’ve stuck with football) with some blue chippers in the minors in the forms of 3B Josh Vitters and OF Brett Jackson. The part of the Cubs situation though that would most intrigue Epstein though is being able to resurrect a franchise and become the one who brought them a championship after over a century of drought. He would have statues and monuments built in Chicago alongside Michael Jordan and Mike Ditka. Now that we’ve addressed Theo going to Chicago lets look at what my faithful Boston Red Sox would do.

In my eyes I don’t see the Red Sox taking a huge step backwards if Theo exited the building. The Red Sox have two in-house candidates who could step in almost immediately in assistant GM Ben Cherington and vice president of player personnel and professional scouting Allard Baird. Remember just because Epstein would have left Boston the Red Sox aren’t going to suddenly spend less money on big league talent or allocate fewer resources towards the draft and international signings. As GM of the Red Sox, Theo has always had the ability when drafting to over reach for players (Casey Kelly, Ryan Kalish, and Blake Swihart were all high schoolers considered too expensive to sign) because he knew finances weren’t in an issue and a mistake could be patched financially. More risks can be taken when cash flow isn’t a major issue. A mistake (hey how you doin’ Mike Cameron?) can be made and be quickly covered up and moved on from with little to no hesitation.

Don’t get me wrong Theo Epstein’s fingerprints are all over the Red Sox organization and the team that they field every night. He has done a marvelous job of architecting a juggernaut that isn’t going anywhere any time soon. The organization is flush with talent even after making a major trade for Adrian Gonzalez and giving up 3 of the their top prospects. The major league squad has the second best record in baseball and is a powerhouse thanks in part to Theo’s philosophies and actions over the past 9 years. What I am saying though is that a figure such as Baird or Cherington would be able to step in and work with the Henry group, a great ownership group who are always looking to win, and keep the Sox going strong. Though the Royals never won a championship or a playoff game under Baird he did bring in talent such as Johnny Damon and Carlos Beltran before being hamstrung by ownership to get rid of all those talented kids he drafted and watched grow. With the Red Sox resources I think he could do a wonderful job and keep the team on the platform they’ve reached for years to come. 

Don’t worry Red Sox Nation if Theo Epstein leaves your beloved Boston Red Sox the team will continue to function as a top tier organization and win ball games in bunches. It’ll just have to be done under someone other than the only man to architect this centuries first multiple championship baseball organization.

Until we cross paths again,

Geoff Jablonski