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

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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.

Clayton Kershaw might return to the Dodgers’ rotation next week

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Dodgers southpaw Clayton Kershaw is nearing his return to the mound, according to club manager Dave Roberts. Both Kershaw (left biceps tendinitis) and fellow lefty Rich Hill (left middle finger blister) are scheduled to toss simulated games on Saturday; depending on the outcome, Roberts says Kershaw could forgo a minor league assignment and slot back into the rotation by Thursday.

Kershaw, 30, was diagnosed with biceps tendinitis as the team closed out their Mexico Series at the start of the month. He has not made a start in several weeks, but was finally able to resume throwing on Sunday and managed to get through two successful bullpen sessions. Though Dodgers’ ace hasn’t been completely injury-free over his 11-year career in the majors, this is the first significant issue he’s had with his pitching arm so far. The team is expected to take every precaution with the lefty, and will likely limit him to just four innings during Saturday’s simulated game.

Prior to his injury, Kershaw was working on another dominant run with the club, sporting a 2.86 ERA, 2.0 BB/9 and 9.8 SO/9 through his first 44 innings of the season. While Kershaw, Hill and left-handed starter Hyun-Jin Ryu served their respective terms on the disabled list this month, the Dodgers utilized a combination of relievers Ross Stripling and Brock Stewart, both of whom impressed during their limited time in the rotation.