The Chicago Cubs and Boston Red Sox have been linked for decades. The two organizations were members in a fraternity of failure, with the Red Sox going 86 years in between World Series wins, and the Cubs still without a championship since 1908. The two nearly met in the 2003 Fall Classic, before both clubs fell to their Championship Series opponents, and Boston's victory in the 2004 World Series took some of the drama out of any future matchup between these teams.
The general manager who helped bring Boston to both that 2003 attempt at glory and the actualized victory of 2004 is now working for the Cubs, keeping a link between the two organizations intact nearly a decade later. A year into his new gig, both he and his new team would be well-served to follow the blueprints drawn up in Boston. By all appearances, that's just what's happening.
While the situations Epstein landed in were different in each city – the Red Sox had won 93 games and finished in second in the AL East in 2002, while the 2012 Cubs featured an aging core that had missed its chance – there were similarities on the farm. Epstein inherited a farm system that had produced little for most of a decade's time, with Nomar Garciaparra arguably the only item worth bragging about from an eight-year period under Dan Duquette, at least until Kevin Youkilis was selected in the former GM's final year at the helm.
Boston had abundant financial resources, and had signed players like Pedro Martinez and Manny Ramirez to lucrative, long-term deals in order to bring them in or keep them around. But they were never able to complement those signings with products from the farm – no, Shea Hillenbrand doesn't count – and it kept Boston from accomplishing the goal they had tried for much of a century to realize.
One of the first things Epstein did when he took over as the team's general manager before the 2003 season was to address this issue. Epstein claimed Boston would turn into a "scouting and player development machine," but was also aware that the Red Sox had "a chance to win it all" in 2003. That's where those financial resources came into play, and will come into play for the Cubs down the road when the time is right. But for now, in year two of a plan that is more longterm than that, the key item from Epstein's arrival in Boston is that player development machine.
Boston expanded its front office under Theo and he has done the same in Chicago, over time hiring or promoting many who are now the general managers of other teams – Padres GM Josh Byrnes, Boston's Ben Cherington, and Chicago's own Jed Hoyer were all assistant general managers under Epstein. An emphasis was placed on scouting and spending on the draft, and it helped lead to Boston's second World Series of the last decade in 2007, when products of the farm system such as Youkilis, Jon Lester, Jonathan Papelbon, Jacoby Ellsbury, and Rookie of the Year Dustin Pedroia contributed significantly both in the regular season and under October's bright lights.
To limit what Boston accomplished under Epstein to that would be selling him short, though, as not only did the Red Sox make good on his promise to become a "player development machine," but they outperformed everyone else in the majors in the process. Wins above replacement is an imperfect stat, but in general, it can give you a good sense of scale over a long period of time. Before the 2012 season, Fangraphs researched who the most successful farm systems of the previous decade (2002-2011) had been, measuring the cumulative wins of all the products of each team's minor-league system. Whether they played for their original team or not wasn't important – the purpose was to measure how effective each team had been at drafting and developing talent over the last decade, whether that talent was used for the team in question, or as part of a trade to another club.
Towards the bottom of the list, coming in at No. 27, were the Cubs. They had produced roughly 20 wins from players they developed over a decade's time. In the same stretch, Theo's Red Sox dominated by producing 100 wins from their minor-league system.
Boston developed tons of talent – more than any other organization according to the above – but they didn't hoard it all. Epstein made trade after trade, sending out prospects for established major-league players to boost the Red Sox' chances of success in the present. He didn't sacrifice the future to do so, though, holding on to essentially all of the very best pieces the farm had to offer, but plenty of worthwhile major-league talent was sent packing from Boston in order to increase the odds of competing in the present.
Pedroia, Ellsbury, Lester, Papelbon, Clay Buchholz, Daniel Bard, and others all stayed put, but the Red Sox made significant trades of significant prospects to achieve their goals of competing. Hanley Ramirez and Anibal Sanchez went to Florida to bring Josh Beckett and Mike Lowell to Boston. Brandon Moss and Craig Hansen returned Jason Bay in mid-2008, when Boston needed to replace Ramirez, who was headed to Los Angeles in that three-team deal. Justin Masterson and Nick Hagadone were packaged for Victor Martinez a year later to solve Boston's catching issue as well as bolster an already potent lineup. Casey Kelly and Anthony Rizzo brought in the last year of Adrian Gonzalez, as well as an opportunity to extend him. David Murphy, Jorge de la Rosa, Freddy Sanchez, Matt Murton, and many more were sent out in similar deals over the years.
If you're as successful as Theo's Red Sox were at drafting and developing players, this is precisely what has to be done with pieces that are far more extraneous than their level of talent implies. Rosters are only so large, whether you're talking about the 25- or 40-man variety, and only so many players can be protected at a time. Trading all of the above while holding on to the pieces that suit the team's needs best makes the most sense for sustained success. Maybe the Red Sox didn't win every single year that they made these trades, but ask yourself this, as Cubs fans: How many prospects would be too many if it meant even one World Series title for your team? Epstein, to his credit, secured two with the help of trades, and pieces from his final years in Boston could be part of the next Red Sox club with the chance to win it all to boot.
The Cubs aren't at that stage of their rebuilding process yet, but with any luck, they'll move into that territory later this decade. They have the basics down already, with a young, talented major-league shortstop in Starlin Castro, the aforementioned Rizzo holding down first base at the age of 23, and outfielder Brett Jackson looking to stick in the majors after debuting in 2012. Jorge Soler was one of Epstein and Co.'s first major youth acquisitions, and he, along with many other far-off pieces, will likely make the Cubs' lower minors more intriguing than the big-league team. While that's depressing in the present, it means positive things for the future – the cavalry could very well arrive at the time that Castro, Rizzo, and Jackson are hitting their respective peaks, and, to bring it back to how Epstein built his teams in Boston, the Cubs have the financial resources to make that time frame count.
That idea of reinforcements is one that Epstein and Hoyer both believe in – Hoyer felt the lack of deep waves of talent was a significant issue in San Diego, one he and current Cubs VP of scouting and player development Jason McLeod helped to resolve in their short time there. Chicago's minor-league talent might all be pooled in the lower portion of the minors now, but consider that the first wave of what, if history is anything to go by, will be many.
There will be some significant differences in how Epstein and his front office can approach the issue of their own player development machine, thanks to the most-recent iteration of the collective bargaining agreement. It puts a cap on international spending while instituting a draft budget based on the number and location of draft picks. Everyone else has to play by those rules as well, though, and Epstein has already shown an aptitude for working within the draft's rules. The right decisions – and the right people making those decisions – can carry Chicago a long way, as they did the Red Sox.