So many questions on Epstein, Cubs

  • The date of Theo Epstein's arrival in Chicago is yet to be determined.

    The date of Theo Epstein's arrival in Chicago is yet to be determined. Associated Press

Updated 10/18/2011 7:04 PM

The NFL trading deadline passed Tuesday afternoon and the Red Sox still hadn't dealt Theo Epstein to the Cubs for Chris Harris.

Boy Wonder Airways apparently grounded all flights from Boston to Chicago, leaving Epstein to sit on the runway dining on baked beans instead of deep-dish pizza.


Goody goody. The lag time in consummating the transaction allows us to ponder pressing questions swirling around Epstein's inevitable arrival.

Q. What has been the hang-up in finalizing the deal?

A. The Cubs offered Crane Kenney as compensation. The Red Sox moaned, "No, no, dear God, no," and asked for Ronnie Woo-Woo instead. The impasse stands at Alfonso Soriano.

Q. People keep warning that Epstein isn't a Messiah or a savior, so what is he?

A. If any Cubs general manager isn't a Messiah or a savior, what he is essentially is overmatched.

Q. So why are the Cubs, their fans and the local media so excited about Epstein?

A. Mostly because Mensa Magazine ordained him the most qualified Theo since Kojak and Huxtable.

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Q. Didn't the Cubs hire someone like Epstein at least once before?

A. You're probably thinking of 1994 and Andy MacPhail, who had won two World Series in Minnesota like Epstein has in Boston.

Q. How did that work out here?

A. All you need to know is that the Cubs still haven't won a World Series in 103 years.

Q. So why are the Cubs considering revisiting the Boy Wonder model?

A. Mostly because it's always a good idea to bring in a fresh set of previously successful eyes to tell ownership how messed up the Cubs are.

Q. That's it?

A. That and no matter who owns the Cubs, whether it be the Wrigley family or the Tribune family or now the Ricketts family, they always believe that if they aren't going to win a World Series they might as well not win one with somebody who already has won one or two.


Q. Like MacPhail and now Epstein, you're saying?

A. And Lou Piniella and Dallas Green and going all the way back to Leo Durocher and all the way forward to myriad players who failed here like Derrek Lee.

Q. OK, so how old is this latest so-called Boy Wonder named Theo Epstein?

A. By the time he gets to Wrigley Field, 37 going on 104.

Q. The Red Sox had problems with players drinking beer in the clubhouse during games, so is that what we can expect from the Cubs after Epstein gets here?

A. Not at all. The Cubs' new agreement with Old Style dictates that all drinking by players during games must take place on the mound and in the batter's box.

Q. You're being silly now, aren't you?

A. Considering we're talking about a franchise that hasn't won even a pennant in 66 years, no, I'm dead serious.

Q. Do you think that by the time this deal is finalized Epstein will understand what he's getting into?

A. THEOretically, yes, considering he helped the Red Sox break an 86-year-old curse. Realistically, no, not anymore than Custer did when he joined the Cubs.

Q. What if negotiations collapse and Epstein doesn't wind up here.

A. The Cubs go to Plan B.

Q. Which would be what?

A. Ronnie Woo-Woo as general manager and Crane Kenney as field manager.

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