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.

The 2017 Yankees are, somehow, plucky underdogs

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There’s a lot that has happened in the past year that I never, ever would’ve thought would or even could happen in America. Many of them are serious, some are not, some make me kinda happy and some make me terribly sad. I’m sure a lot of people have felt that way in this oddest of years.

There’s one thing in baseball, however, that still has me searching my feelings in a desperate effort to know what to feel: The New York Yankees are the postseason’s plucky underdogs.

This is not about them being lovable or likable — we touched on that last week — it’s more about the role they play in the grand postseason drama. A postseason they weren’t even supposed to be in.

None of the three writers of this website thought the Yankees would win the AL East or a Wild Card. ESPN had 35 “experts” make predictions back in March, and only one of them — Steve Wulf — thought the Yankees would make the postseason (he thought they’d win the division). I’m sure if you go over the plethora of professional prognosticator’s predictions a few would have the Yankees squeaking in to the postseason on the Wild Card, but that was nothing approaching a consensus view. Their 2017 regular season was a surprise to almost everyone, with the expectation of a solid, if unspectacular rebuilding year being greatly exceeded. To use a sports cliche, nobody believed in them.

Then came the playoffs. Most people figured the Yankees would beat the Twins in the Wild Card game and they did, but most figured they’d be cannon fodder for the Indians. And yep, they fell down early, losing the first two games of the series and shooting themselves in the foot in spectacular fashion in the process. Yet they came back, beating arguably the best team in baseball and certainly the best team in the American League in three straight games despite the fact that . . . nobody believed in them.

Now we’re in the ALCS. The Astros — the other choice for best team in the American League if you didn’t think the Indians were — jumped out to a 2-0 lead, quieting the Yankees’ powerful bats. While a lot of teams have come back from 0-2 holes in seven game series, the feel of this thing as late as Monday morning was that, even if the Yankees take a game at home, Houston was going to cruise into the World Series. Once again . . . nobody believed in them.

Yet, here we are on this late Wednesday morning, with the Yankees having tied things up 2-2. As I wrote this morning, you still have to like the Astros’ chances given that their aces, Dallas Keuchel and Justin Verlander, are set to go in Games 5 and 6. I’m sure a lot of people feel still like the Astros’ chances for that reason. So that leads us to this . . .

It’s one thing for no one to have, objectively, believed in the Yankees chances. It’s another thing, though, for the New York Yankees — the 27-time World Champions, the 40-time American League pennant winners, the richest team in the game, the house-at-the-casino, U.S. Steel and the Evil Empire all wrapped into one — to officially play the “nobody believed in us” card on their own account. That’s the stuff of underdogs. Of Davids facing Goliaths. Of The Little Guy, demanding respect that no one ever considered affording them. If you’re not one of those underdogs and you’re playing that card, you’re almost always doing it out of some weird self-motivational technique and no one else will ever take you seriously. And now you’re telling me the NEW YORK FRIGGIN’ YANKEES are playing that card?

Thing is: they’re right. They’ve totally earned the right to play it because, really, no one believed in them. Even tied 2-2, I presume most people still don’t, actually.

I don’t know how to process this. Nothing in my 40 years of baseball fandom has prepared me for the Yankees to be the David to someone else’s Goliath and to claim righteous entitlement to the whole “nobody believed in us” thing.

Which, as I said at the beginning, is nothing new in the year 2017. I just never thought it’d happen in baseball.