Barring a breakdown that would truly be Chicago Cubs-like, Theo Epstein, the General Manager who helped guide the Boston Red Sox to two World Series titles, will assume similar duties, albeit with a fancier title, on the North Side of the Windy City. He will undoubtedly bring a host of quantitative analysis skills and staff to Chicago, and he will also bring a unique firsthand knowledge of what it’s like to work with a large, maniacally obsessed fanbase whose ravenous hunger for a title is a vortex of need. If he succeeds, he’ll certainly be one of the few team executives inducted into the Hall of Fame at his earliest eligibility.
His first impact may not be in the free agent market; free agents may want to steer clear of a team’s whose last three seasons are of 83, 75, and 71 wins. Instead, Epstein could make an impact by improving the Cubs abysmal track record in getting their top prospects to translate their minor league success in the big leagues. During Epstein’s reign in Boston Jon Lester, Clay Buchholz, Jonathan Papelbon, Dustin Pedroia and Jacoby Ellsbury all moved smartly from stars at Pawtucket, Portland, Salem et al to stars at Fenway (and more talent is on the horizon with Josh Reddick and Ryan Lavarnway penciled in for a role on the 2012 Red Sox). By contrast few top Cubs prospects have done the same. Felix Pie, Tyler Colvin, Josh Vitters, Geovany Soto, Jeff Samardzija have all struggled. Only Soto has shown star like potential, and he has been maddeningly inconsistent. Starlin Castro has been the exception that proves the rule, but a player who has walked just more than five percent of his first 1200 plate appearances could crater at any moment.
The Cubs farm system is currently deep with players who project as solid but not star potential players: Vitters, Brett Jackson, Chris Carpeneter, Chris Archer and several others. With the Cubs track record, those players would likely top out as Quadruple A hitters and long reliever type players, but with a revamped set of instructors in the minor league system then they can become the supporting cast or better for the next winning team at Wrigley. It won’t be the most glamorous of tasks but it may be the easiest gauge to measure Epstein’s early performance.