Sports: How The Chicago Cubs Lost the Red Sox-Dodgers Deal

During his first year as the General Manager in Boston, Theo Epstein got a solid dose of Red Sox Nation frustration by experiencing the 2003 Game 7 ALCS meltdown.  Now, in his first year on the job running the Chicago Cubs front office, Epstein is getting a solid dose of what it’s like to be part of the Windy City’s long suffering base, but the losses are quieter and much less public.

This weekend’s mammoth blockbuster (yeah it really requires two gargantuan adjectives) trade that sent a quarter of a billion dollars in contracts and the talents of Adrian Gonzalez, Carl Crawford, Josh Beckett and Nick Punto from Boston to the Los Angeles Dodgers in exchange for James Loney and some minor league players  is startling; rarely does a perennial contender gut its roster in the late stages of the season, but the sense of WTF in the Chicago Cubs front office must have been audible and long.  Now a second avenue of rebuilding has become more treacherous and narrow.

When Epstein took over last November, it was widely assumed that he would build the Cubs in the same manner that helped the Red Sox break their curse and win two World Series.  However, weeks after Epstein accepted the Cubs position, Major League baseball announced a new collective bargaining agreement that made it harder for teams to build through the annual summer draft, thus diminishing one of Epstein’s key tools.  With the potential pool of talent through the draft now narrowed, Epstein found a tighter market at the July 31 trade deadline; few teams were willing to trade top flight young talent for eight week rentals of veteran players to help their drive toward the playoffs.

The alternative and far less geeky scenario for roster reconstruction in Chicago was to be aggressive in the free agent market (sort of an MLB equivalent to being the NFL’s Washington Redskins), and to be a willing home for team’s unwanted players (kind of an MLB equivalent of football’s Cincinnati Bengals).  The first scenario will play out this winter, but toward the second end, Beckett was probably near the top of Epstein’s list.  Yet now it appears that the Dodgers are interested in playing that game too.  This summer they also acquired former Miami Marlins infielder Hanley Ramirez.  And unlike the barren cabinet that Epstein inherited from his predecessor, Jim Hendry, the Dodgers system is stocked with prospects that will attract trade partners with embattled players to move.

For some Cubs fans this weekend’s trade will spark daydreams of trading Jeff Samardzija and Josh Vitters for Jon Lester and Jacoby Ellsbury, but I think the Red Sox are done dealing.  I think they wanted to rid themselves of Crawford and Beckett, and giving up A-Gonz was the price of doing business.  Any NBA fan will tell you that to lose bad contracts, you usually have to give up talent (the exception involves trading with the Wizards who seem to like bad contracts).  As constituted, Red Sox GM Ben Cherington goes to the winter meetings looking to build on a foundation of homegrown talent like Lester, Ellsbury, Dustin Pedroia, Clay Buchholz, a pretty nice core four, plus emerging talent in Will Middlebrooks and Ryan Lavarnway.  That nucleus plus a wad of cash could be turned into a contender pretty quickly.

Meanwhile, at Wrigley, the road to reversing their curse–no titles in 104 years and counting–gets longer.  Epstein knew he was taking on a complex challenge, but he probably had to idea that the degree of difficulty would spike.


About jmartin437

I've worked in and around the world of high end cheese for 27 years. I've been everything from a department manager who hired and fired and trained staffs to a weekend warrior who shows up ties on an apron the middle of a rush and talks to customers and cleans up the place. I enjoy it all, and I especially like my current situation conducting informal seminars about cheese at area bars and in class at the 92nd St. Y. The current schedule is always up at In addition I conduct private events that are perfect to lead off birthday parties for foodies and sommeliers and also they make great entertainment for corporate team building events and associates meetings at law firms. In addition, I've been a freelance journalist for 27 years. Currently my profiles of leading musicians and filmmakers appear in the Wall Street Journal and I also wrote about sports for the Root, and for five loooong years, which included the entirety of the Isiah Thomas Knicks era, I wrote about the NBA for the New York Sun. I enjoyed writing about basketball so much that I now do it here at rotations for free.
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