In Theo We Trust?

Theo Epstein is in the midst of his third winter as the man in charge of the Chicago Cubs, but he’s still not giving Cubs fans much to be excited about. Epstein was the general manager who led the Boston Red Sox to their first World Series championship in 86 years when they won in 1918, and a second title in 2007. In 2011, he left the Red Sox for the Cubs to have more control over baseball operations and for a chance to become a legend in the world of baseball executives. Winning in Boston is one thing, but to also be the guy to lead the lowly Cubs, the most miserable franchise in professional sports, he could be the greatest executive of all time. Since then, the Cubs are still among the worst teams in baseball, while the Red Sox team he left in the hands of Ben Cherington followed up their hitting of rock bottom in 2012 with a World Series title in 2013. Should Cubs fans still have faith in Theo to take them to the promised land?

First off, let’s compare the levels of misery that the Red Sox and Cubs had been through prior to Theo Epstein. A lot of people like to lump Red Sox fans and Cubs fans together as kindred spirits, but the reality is that Cubs have been so much worse throughout their history that it’s not fair to compare. The Red Sox went 86 years without winning the World Series, but at least they were relevant in the years between. The Sox made it to Game 7 of the World Series four times in that span, falling to the St. Louis Cardinals in 1946 and 1967, the Cincinnati Reds in 1975, and the New York Mets in 1986. There were other years where they were close, falling to the Yankees in heartbreaking fashion most notably in 1978, 1999, and 2003. When the Red Sox only managed 69 wins in 2012, it was their worst season in 50 years, but for the Cubs that’s a much more regular result. The Cubs last won the World Series in 1908, and last reached the World Series in 1945. They have the occasional year like 2003 or 2008, but inevitably crumble in October. They’re the Cubs. That’s what they do. After that, they fall back to earth the following year and become the awful team we know and love yet again. With the Cubs, losing is familiarity, with the Red Sox, losing is agony becuase they were so close to winning.

The most overrated aspect of Epstein’s job performance in Boston was his ability to to actually build a championship roster. In reality, Theo inherited a very good roster built by Dan Duquette. The Cubs may have had some young talent in the system when Theo arrived in Chicago, but the Red Sox of the early 21st Century already had Jason Varitek, Derek Lowe, Tim Wakefield, Nomar Garciaparra, PEDRO MARTINEZ, and MANNY RAMIREZ. That’s right. It’s a lot easier to build a World Series winning roster if the roster you’re given already has one of the best right handed pitchers and one of the best right handed hitters in the history of baseball on it. In 2005, Theo left the Red Sox during the offseason, but was brought back before the 2006 season started. During the interim, Epstein’s assistants Jed Hoyer (who is now the Cubs’ GM still working under Theo) and Ben Cherington (who is now the GM of the Red Sox) made a franchise altering trade that Theo never would have made when they sent shortstop prospect Hanley Ramirez to the Florida Marlins in exchange for starting pitcher Josh Beckett and veteran third baseman Mike Lowell. Even though things did not end well with Beckett and the Sox, this was a good deal for the team. The Red Sox do not win the 2007 World Series without this deal, as Beckett was the ALCS MVP and Lowell was the World Series MVP that year. It’s hard to give Epstein a ton of credit for that one.

The Red Sox and the Cubs are both committed to building their teams through the draft and their respective farm systems, but so far Ben Cherington is looking like more of a genius than his former boss. Epstein and Cherington did a good job of drafting and developing prospects who are now producing for the Red Sox. The Cubs’ farm system was in bad shape when Theo took it over, but he’s been reluctant to make any big free agent signings to help the team compete in the meantime. Cherington won a World Series by striking a balance between young prospects like Xander Bogaerts and Will Middlebrooks and affordable veteran signings like Shane Victorino, Mike Napoli, David Ross, and Koji Uehara to go with the core of David Ortiz, Jacoby Ellsbury, Dustin Pedroia, and Jon Lester, who were all on the 2007 team. Epstein is being patient with the farm system, but if he was in a different city, his seat might be a little hotter going into 2014.