Thinking About Thinking

The 10 Worst Moves By Red Sox GM Theo Epstein

Posted in Uncategorized by larrycheng on August 17, 2009

Since it’s the dog days of summer and the Red Sox are wilting, I need to drown my baseball sorrows by evaluating Theo Epstein’s 10 worst moves as Red Sox general manager.  VCs are often defined by their winners, rather than their losers.  Unfortunately, life isn’t so easy for baseball GMs.  Without further ado:

  1. Freddy Sanchez (.300 career batting avg, all-star), traded with Mike Gonzalez for Jeff Suppan, Brandon Lyon, and Anastacio Martinez. 
  2. Matt Clement, free agent pick-up.  4 years, $40M.
  3. J.D. Drew, free agent pick-up.  5 years, $70M.  He’d be #1 or #2 except he actually plays once in awhile. 
  4. Julio Lugo, free agent pick-up.  4 years, $36M. 
  5. Edgar Renteria, free agent pick-up.  4 years, $40M.
  6. Doug Mirabelli, traded away Cla Meredith (3.57 career ERA) and Josh Bard (.261 career batting avg). 
  7. Eric Gagne, traded away David Murphy (.280 career batting avg) and Kason Gabbard. 
  8. Bronson Arroyo (4.35 career ERA), trade for Wily Mo Pena. 
  9. Jeremy Giambi, traded away Josh Hancock (4.20 career ERA). 
  10. Daisuke Matsuzaka, 6 years, $52M plus $51.11M posting fee.  Tough call, but not looking good.

If there’s a lesson learned from Theo’s free agent mistakes that in its own way applies to the venture business – it is to be willing to pay up for the sure thing.  Now you could say there is no sure thing, which is fair.  But the closest thing is someone like Mark Texeira who had 30–40 home runs and .380 OBP in his bad years prior to being signed by the Yankees (away from the Red Sox).  Alex Rodriguez in his bad years still hit 30 home runs with a .400 OBP prior to once again being signed by the Yankees (away from the Red Sox).  Theo seems to like to pay $10M-$15M/year for above average historical performance (J.D. Drew, Julio Lugo, Matt Clement, Daisuke Matsuzaka, etc.), but not $20M for spectacular historical performance.  Ironically, a great example of the latter category is Manny Ramirez, not a Theo signing, but also an example of a sure thing (when mixed with PEDs). 

That all being said, the Boston Red Sox have have won two World Series championships during the Theo Epstein era.  So, I am still a Theo Epstein fan.  Maybe like VCs, baseball GMs are defined by their winners after all. 

11 Responses

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  1. busyevent said, on August 17, 2009 at 11:41 pm

    Make it easy on yourself . . . become a Cardinals fan!

    Pujols, now Holliday, Yadie, Schumacher and the pitching . . . oh my!

    And . . . $35MM LESS salary that the BoSox. And . . . arguably the best player in baseball makes about the same as Drew (you wonder why we let him go?).

    So, seriously, ease your pain, relax and enjoy the sound of hitting, sliding, roaring crowds and a great NEW ballpark . . . ain’t it obvious?

    • larrycheng said, on August 26, 2009 at 10:24 pm

      The Cardinals seem to pick up our cast offs – Julio Lugo, John Smoltz – and turn them into all-stars. It’s painful to watch – kudos to their coaching I guess.

  2. David Desrochers said, on August 18, 2009 at 9:16 am

    This is a good list and it shows that Theo seems to have a blind spot when it comes to signing free agents (Drew, Lugo, Rentaria, Clement). I suspect that a similar list could be compiled for any GM in any sport. Even Auerbach made a mistake now and then (any one remember Sidney Wicks and Curtis Rowe).

    This list has the benefit of hindsight. After Matsusaka’s first or second year when he won 15 and 18 games respectively he probably would not have made the list. Likewise when the Red Sox traded their 5th starter and 5th outfielder for a former Cy Young award winner (Gabbard and Murphy for Gagne) who would have guessed that the Cy Young winner would be out of baseball, the outfielder would be a decent everyday player and the pitcher would be re-acquired by the Sox. Both GMs and VCs need to be able to determine who will be a winner and who will be a non-winner and all measurements will be made from the decision point forward. Few will remember how sound the investment was when the actual decision was made.

    A VC is usually looking just at the farm system and making decisions to determine who will make the big league. The farm system (not unlike a VCs “deal flow”) has far more non-winners in it than it does winners.

    VCs and GMs are both defined by their winners. Their non-winners is what keeps them focused and determined to find the best available investment.

    • larrycheng said, on August 26, 2009 at 10:25 pm

      David – totally fair that everyone has their fair share of bad deals. I’m still a Theo fan, he’s done a great job all and all.

  3. Desmond Pieri said, on August 19, 2009 at 10:54 am

    Great list. Thank you (I think) for putting all the bad news in one post! The scary thing is that when you go from 1st to 10th, they are all such bad moves; the “quality” never drops off. Any one of them could be put at the top of the list.

    Alas, I too remain a Theo fan. True, he is only able to get away with this because his “fund” is so large (i.e. Henry’s wallet.) But what he’s done best is the quality of the farm system. It is so refreshing to see these players come up and do so well at such a young age.

  4. Phil said, on August 27, 2009 at 2:15 pm

    I think Smoltz should be on the list too, maybe Penny. These two bad moves may end up costing them the 2009 season

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