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Theo Epstein in Chicago: Can he break a second curse?

Oct 12, 2011, 10:29 AM EST

Theo Epstein

The first thing most people thought when the rumors of Theo Epstein possibly joining the Chicago Cubs began to circulate was “can he do it again?”  Can the man credited with ending baseball’s most famous world championship drought end baseball’s longest?  Now that Epstein and the Cubs have a deal, it’s worth taking a look at the challenge facing him in Chicago and asking ourselves if Theo Epstein can make lightning strike twice.

There are no guarantees in life, but there is reason to be optimistic about Epstein’s chances to turn the Cubs into a winner. Why? Because many of the same challenges he faced when he took over the Red Sox exist with the Cubs.

Epstein is very familiar with the overall milieu in which the Cubs currently find themselves. When he took over in Boston he inherited a franchise with a dispirited and fatalistic fan base and a team which called a near-dilapidated ballpark home.  He changed the mood soon after he arrived and helped change the narrative as ownership embarked on substantial ballpark renovations.  No, you can’t credit Theo Epstein with all of that — it was John Henry’s dollars which transformed Fenway Park from a place which had seen better years into a perpetually-sold out gem — but Epstein knows what faces the Cubs in this regard.

More substantively, at the top of the Cubs’ list of baseball-needs is fixing a farm system that, while recently spitting out a gem in Starlin Castro, seems to be much better at coming up with role players instead of future stars.  WEEI’s Alex Speier writes today about how back in 2003 Epstein made it his first mission to build a “scouting and player development machine.” While many of Epstein’s big-ticket free agent signings have been busts recently, he and his able assistants — many of whom went on to become general managers themselves — revamped the Red Sox’ player development apparatus.

Indeed, in his first three drafts, Epstein chose Jonathan Papelbon, Dustin Pedroia, Clay Buchholz and Jacoby Ellsbury. It may be hard to see player development as a strength of Epstein’s today given that he’s become more notable for high dollar free agent signings — and given that the young talent that he has acquired in recent years has been dealt to land players such as Adrian Gonzalez — but a steady stream of talent has been developed under Epstein’s watch and such an approach should be Epstein’s first task when he starts work this fall.

Finally there’s the matter of all of that expensive aging talent on the Cubs’ roster.  Yes, we are fixated on the Red Sox’ big bad contracts right now (e.g. John Lackey and Carl Crawford), but it doesn’t take too much effort to look back at what Epstein did in his early years in Boston to see that he’s the right man to fix the Cubs’ case of Chronic Bad and Expensive Syndrome.

Epstein cast off popular but aging and expensive stars like Pedro Martinez and Nomar Garciaparra. He got rid of Manny Ramirez despite his still-elite production when his antics became too much to bear. He made what we forget now were bargain moves like snagging David Ortiz and locking up young stars like Pedroia, Jon Lester and Kevin Youkilis to long-term contracts before they got expensive in arbitration.  He stuck with the then-young and rising Lester and declined to include him in a package for what was thought to be a sure-fire ace in Johan Santana.

Now transfer those examples to the Cubs.  Is there any doubt with that track record that Epstein will be able to figure out that the next winning Cubs team will not have guys like Alfonso Soriano and Carlos Zambrano playing critical roles? Is there any doubt that he’ll be able to ensure that Starlin Castro gets locked up and becomes the centerpiece of the club going forward? That he won’t make shortsighted moves to trade for veterans who, while well-known, aren’t suited for where the team currently finds itself on the success cycle?

Like I said above: there are no guarantees.  If the last month of baseball has shown us, predicting baseball is a sucker’s game.  Epstein may flop in Chicago and the title drought may go to 200 years before it ends.  But as one looks around the game, one would be hard-pressed to find a person more familiar with the challenges facing the Chicago Cubs and with a more successful track record at addressing those exact challenges than Theo Epstein.

It’s a great hire. And one that should give Cubs fans real hope for the first time in a long time.

  1. yankeesfanlen - Oct 12, 2011 at 11:07 AM

    I can see it now- 2014 World Series, game 5 in Wrigley field- top of the ninth, ARod and Granderson on, batting fifth Jesus Montero- it is high, it is far, it is gone- Yanks up by two, Robertson puts ‘em down in order- Yanks capture Championship #30.
    See?- I’m better now!

    • uyf1950 - Oct 12, 2011 at 11:28 AM

      How are you doing today my friend? I see you are being very conservative in how many championships the Yankees will be going for in 2014. That’s a joke.

      I think it’s going to take longer than 2014 for the Cubs to be in a World Series game.

    • phukyouk - Oct 12, 2011 at 12:07 PM

      so if Grandy and Arod are on base then Robbie struck out?

      • brianbowman16 - Oct 12, 2011 at 3:16 PM

        no, arod struck out, but a new rule implemented by Torre allowed him to bat again, and he singled

    • jaguar49 - Oct 12, 2011 at 3:22 PM

      Typical dumbass Yankee fan — how about commenting on something related to the Cubs getting Epstein. After all, that’s what the story is about, not you bunch of has been millionaires.

  2. Nick C - Oct 12, 2011 at 11:12 AM

    Much bigger job in Chicago IMO. While Boston consistently came close and then failed, the Cubs rarely even come close. Also, Wrigley Field is a dump and there are few options for fixing it. They will not be getting money from the City of Chicago (broke) or Cook County (broke) or the State of Illinois (broke) for renovations. Thus all $$ to fix/upgrade it will have to come from the owners’ pockets.

    On top of the stadium issues, you have a farm system that is bereft of any high end talent especially on the pitching side. On the other hand, the Cubs do have some payroll flexibility. I could easily see them landing Prince Fielder. Even if they land Fielder, they have holes at 3b and RF, they have subpar players at LF, 2b, and CF and they have a rotation that is average at best with no frontline starter. Oh and they have the enigmatic Marmol at closer.

    Theo will help (impossible to be worse than Hendry) but I don’t see them winning a World Series anytime soon.

    • 18thstreet - Oct 12, 2011 at 12:47 PM

      Wrigley Field is not a dump. It needs a better scoreboard. It needs some paint. But it’s a fine place to watch a game.

      All these people who want to blame the ballpark: explain how the Twins won in the Metrodome?

      • Alex K - Oct 12, 2011 at 4:32 PM

        I don’t think there is anything wrong with the scoreboard. Would a jumbotron enhance your enjoyment of the game that much? Or do you really want the Cubs to get more advetising revenue?

        Wrigley is a wonderful place to watch a baseball game. It’s not the nicest facility, but it’s not like there is no upkeep done.

  3. proudlycanadian - Oct 12, 2011 at 11:12 AM

    The answer to the question posed by Craig is NO!

  4. Chris St. John - Oct 12, 2011 at 11:15 AM

    I put together (as best I could from MLB Trade Rumors and Baseball-Reference) a transaction history for Theo Epstein in a Google Doc. It’s missing a lot of the numbers for signings, but should have a lot of the names: http://stealofhome.wordpress.com/2011/10/11/theo-epsteins-transaction-history-with-the-boston-red-sox/

  5. Kevin S. - Oct 12, 2011 at 11:22 AM

    Zambrano and Soriano are in no way comparable to Nomar, Pedro and Manny. The latter three were dealt/let go when they were still providing surplus value on their contracts. The former two represent four years and $76 million of dead weight. Yes, I’m sure Theo wouldn’t re-sign Soriano right now. Too bad he doesn’t get to make that decision until November 2014.

    • El Bravo - Oct 12, 2011 at 11:56 AM

      You’re right. Soriano isn’t going anywhere. He was literally signed the off season directly after his career year. Everyone knew it, stat geeks and traditionalists alike, yet that ownership at the time bit hard and long term. Epstein would never have made that move, he was too busy making good ones and winning championships. Despite the albatrosses left on the roster, I think the Cubs have a lot to root for b/c whether or not he’s good, he’s better than his predecessor by a long shot.

      • bigharold - Oct 12, 2011 at 6:10 PM

        “Epstein would never have made that move…”

        No, he’d make moves like Rentiria, Drew Lugo Cameon, Lackey, Matsuzaka, Jenks and Crawford.

        Frankly, I’d say we’re about to find out just how good Epstein is, (and personally I think he’s been overrated), because his past history with FA signing, especially big dollar ones, is pretty bad.

        He is a bit better a player development but can he turn the Cubs around before he gets canned? If he can he’ll be a baseball God. But, there’s no Manny, Ortiz, and Martinez on the Cubs. If he can’t, he’ll be remembered as the guy that took Dan Duquett’s team and broke the curse then won another WS due in large part to two players, Beckett and Lowell that he didn’t trade for because he took it on the lam in a gorilla suit. And, in the end left the RS in disarray, .. including their farm system.

  6. jb4820 - Oct 12, 2011 at 11:48 AM

    Let me see if I get this straight….the bosox get rid of Epstien and Francona, two guys who ended an 86 year curse, after winning two championships in 4 years??? Sounds eerily similar to selling the Babe after winning 3 championships in 4 years. Unreal.

    • fieldingmellish - Oct 12, 2011 at 12:38 PM

      Yeah, selling the best baseball player, i.e. the man who is the best person at actually playing the game of baseball on a field, is definitely comparable to letting go of a (good) manager and a (good) general manager.

      Jesus, you’d think they just let John McGraw and Branch Rickey walk.

    • bozosforall - Oct 12, 2011 at 2:10 PM

      Then again, the Red Sox organization is HISTORICALLY one of the most inept franchises in MLB. Even a blind squirrel finds a nut every once in awhile (2004, 2007) though the nuts that they found were shrivelled up due to the excess steroid usage by their big heroes, Ramirez and Ortiz.

  7. El Bravo - Oct 12, 2011 at 11:49 AM

    The Cubs should consider this a coup. Unbelievable really. I don’t think Epstein leaves if the Sox had made the playoffs, or perhaps went a bit deeper into the playoffs, at least. I think there was a direct correlation between the clubhouse collapse and this move. The Cubs won’t be great immediately, but I expect to see some positive gains in their system fairly soon and that should give returns out on Wrigley field in a few seasons. It is cause for optimism, but pessimism rules on the North Side, so a lot of ground shaking will have to be done to uproot that mentality.

  8. diehardcubbiefan4life - Oct 12, 2011 at 11:59 AM

    Being a Die hard Cubs fan, I will admit that the Cubs won’t be great immediately. But with the way that Theo drafts, builds, and rebuilds, I think we can expect a decent contender by 2015

  9. Nick C - Oct 12, 2011 at 12:04 PM

    Joe Posnanski weighs in as only he can: http://joeposnanski.si.com/2011/10/12/the-cubs/

    • El Bravo - Oct 12, 2011 at 1:01 PM

      I know a lot about the Cubs but still I feel a bit enlightened after reading that.

    • Kyle - Oct 12, 2011 at 1:28 PM

      That guy is pretty good at writing words about sports.

      • 18thstreet - Oct 12, 2011 at 3:32 PM

        That guy is good at writing about grass growing and paint drying.

  10. evanhartford - Oct 12, 2011 at 12:22 PM

    Craig, almost all of the positive moves you referenced regarding Theo had nothing to do with 2004 and ending the world series drought. Also, you can’t simply give Theo all the credit for all the good that’s happened to the Red Sox in the last decade without blaming him for all the bad. With the benefit of hindsight, Theo has made plenty of smart moves and dumb moves with the Red Sox.

    But the same can be said for most baseball GMs. So long as you’re a subscriber to Sabermetrics, have you looked at Theo’s WAR as compared to other GMs? Have the Sabermeticians even developed a way to measure manager and GM performance besides the “outdated” metrics, like wins and world championships? A lot of things go into winning a world championship. I’d argue that most GMs have a relatively small impact due to their very limited shelf life and the fact that they don’t start with a clean slate. Theo will inherit the Cubs issues and will have basically 5 years to turn them around significantly. The expectations will be unreasonably high and it will force him to make higher risk moves. Were I a betting man, I’d bet against them winning a world championship during his tenure.

  11. icanspeel - Oct 12, 2011 at 12:28 PM

    Find a way to sign Albert Pujols and he will turn it around very quickly.

  12. 18thstreet - Oct 12, 2011 at 12:48 PM

    I love Theo, but there are a lot of smart GMs out there. Good managers, I think, are a lot harder to find.

  13. bozosforall - Oct 12, 2011 at 2:11 PM

    The Red Sox organization is full of idiots. Brings smiles to the faces of Yankee fans everywhere.

  14. j0esixpack - Oct 12, 2011 at 2:45 PM

    As a Red Sox fan I’m really pulling for Theo to break another curse

    As a Red Sox fan I also know that Theo’s made his fair share of bad moves (many good ones too) and that its time for him to move on.

    But nothing would make most Red Sox fans happier than to see the Cubs end their long and painful drought.

  15. Old Gator - Oct 12, 2011 at 3:25 PM

    I think it may be premature to credit Theo with having broken the curse. Judging from the way things are going in Boston now and especially by the way they imploded this season, it may be that he only stunned the curse – and is fleeing to Chicago upon realizing that, like Cthulhu, the Curse is rising again in a new and even more virulent form.

  16. goldensombrero3000 - Oct 12, 2011 at 8:06 PM

    What’s going to happen to Theo’s and Peter Gammon’s Band now that Theo is in Chicago? Wail with Jeff Tweety? Yeaaah (devil horns). stupid.

  17. diablito0402 - Oct 12, 2011 at 11:49 PM

    Wow if this young punk can pull this off, he will be an imortal baseball god, two curses broken,, this guy will get all the a$$ he wants

  18. pisano - Oct 13, 2011 at 12:08 AM

    It all depends on how much money the Cubs will let Boy Blunder blow before they dump him. I don’t think there are many teams that will let him throw away money on the useless free agents that he brought to Boston. 220 mil alone last year on two of the biggest disappointments in baseball. If he keeps on the rail he was on, he won’t last the five year contract. Theo, keep the gorilla suit handy.

  19. txnative61 - Oct 13, 2011 at 3:03 AM

    I’m a Mariners fan and we never even sniffed a World Series, much less won one. Never heard mention of a curse. There is an attitude I find helpful however. The standings are always going to include many teams in big middle, ones on the bottom, and a few near the top, but only one at the top. There is a point for highly paid players that money ceases to have meaning or motivate them. Young, inexperienced, lower paid players often perform better, have more enthusiasm, and enjoy playing more, even if losing. I enjoy watching the kids play more than calloused veterans. Nice to see Doug Fister doing well, and sometimes seems we are actually the league’s farm system, but in the end, well, somebody’s got to fill the spot in the standings.

  20. diablito0402 - Oct 13, 2011 at 9:41 AM

    What about the yankees, spend around 300 mill every year this past decade and one championship to show for it?? Sorry, trying to buy a ring dont work!!

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