Chicago Cubs: The best and worst of Theo Epstein

(Photo by Jamie Squire/Getty Images)
(Photo by Jamie Squire/Getty Images) /

Theo Epstein achieved immortality with the Boston Red Sox and Chicago Cubs. But forgotten among the highs are the lows that come with any executive.

In his young, but lengthy career building baseball teams, Chicago Cubs President of Baseball Operations Theo Epstein led two major franchises out of the wilderness to World Series victories.  He is, almost with a doubt, headed to Cooperstown.

One month out from the nonwaiver trade deadline let’s review the track record of the most impactful Cubs executive since Andy MacPhail.

Please note, as we take a look at Theo’s greatest hits and swing-and-misses, I want to be clear. This is not some hit piece nor is it a rah-rah effort, but rather an attempt at a sober-eyed analysis.

Boston Red Sox signings and trades

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Everyone remembers the flier Theo took on David Ortiz in 2003.  Theo signed the on-and-off slugger to a one-year, $1.2 million deal.  Ortiz then went on to play 14 seasons with the Red Sox racking up two World Series wins, six Silver Slugger Awards, nine All-star appearances and two postseason MVP awards.

in 2011 as Theo’s tenure came to an end in Boston, Peter Abraham at reviewed Theo’s transactions far more succinctly than I could here. There were some outstandingly good moves and some busts (hey, no one is perfect, especially in baseball).

What struck me was the very good signings and that among the free agent blunders how many were pitchers.

The biggest risk a front office can take is to sign a player to a long-term, big money deal.  If that deal works out you get only what you paid for, and if it doesn’t you look really bad.  What is notable in Boston is that Theo’s best signings were mostly short-term deals like the Ortiz deal.  Among his worst were long terms deals–and especially long-term free agent deals for pitchers.

Chicago Cubs signings and trades

It is impossible to compare Theo’s actions in Boston vs. Chicago because the two teams were in completely different places when Theo took over.   When Theo became GM in 2003, this was a team ready to win.  Many of the pieces were in place to win the 2004 World Series and compete well beyond 2004.  The Cubs in 2012 when Theo arrived were, in short, a catastrophe in every way as ESPN’s Tim Keown described.

But now we have a body of work to gauge Theo’s efforts.  Like in Boston, it reveals on balance better trades than free agent signings and some very shrewd moves.  Trading Scott Feldman and Steve Clevenger for Pedro Strop and Jake Arrieta makes the Brogglio for Brock trade look like a baseball card deal between kids.

But his signing of free agent pitcher Edwin Jackson ranks as one of the worst moves of his tenure in Chicago.  And while many will want to assert the Darvish signing is worse, we just don’t know yet.  I’m sure we’ll cover that topic ad nauseam all six years of Darvish’s contract.

There are not many baseball executives more capable than Theo Epstein.  You could rightfully argue that Astros general manager Jeff Luhnow is better, but only by degrees.  As much as one might try to find a pattern, one doesn’t exist except in one case–signing free agent pitchers.  Everyone has their kryptonite and that might be Theo’s.