How Will Theo Epstein End The Cubs' Century Of Failure?

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Many have tried. All have failed. The Cubs' World Series drought has reached epic length. Can Theo Epstein be the one to break it?

The Chicago Cubs have not won the World Series since 1908.

If you listen to or watch virtually any national broadcast the Cubs are involved in, one of the announcers will mention this. Over and over and over, in fact. Frankly, Cubs fans are sick of hearing about it.

But it's the truth, and since then, four ownership groups, at least 18 general managers (or men with similar responsibilities) and 49 field managers have failed to bring another world championship to the North Side of Chicago. Some have come close; the Cubs were six outs from the World Series in 1984 and five outs away in 2003. (Let's see... carry the three... that means they ought to get there by 2079, one out closer every 19 years.)

Tuesday, Theo Epstein was put in charge of trying to bring the Cubs to the Promised Land, where trophies are won and parades given for winning baseball teams. He's accomplished that in nine years guiding his boyhood and hometown team, the Red Sox. You know the details; his leadership helped the Red Sox erase their drought, his teams made the playoffs six of his nine years, had winning records all nine, and won two World Series.

But Chicago is different. Two big-name managers who had led teams to World Series -- Dusty Baker and Lou Piniella -- were hired in recent years to lead the Cubs there. They knew how to do it, it was said. But when they both left Chicago, chewed up and spit out, both admitted they had no idea what they were getting into.

Theo Epstein said all the right things at his introductory news conference before what observers said was the biggest turnout ever for such an event at Wrigley Field, well over 100 reporters and photographers, including this writer. He praised the Ricketts family, Cubs fans and also his time in Boston. He said in addition to growing up a Red Sox fan, he also watched the Cubs on TV via WGN every afternoon after school, and understood what Cubs fans did about growing up that way, watching day baseball in an historic ballpark.

But he also understands that in modern baseball, analyzing data about players using modern metrics is important -- and he also understands it's not the be-all and end-all of player analysis. Epstein said, "The best organizations use both scouts and data. I want to hire the best scouts and best analysts, and view things through both an objective and a subjective lens."

This is something that's been missing from Chicago Cubs baseball since ... well, forever. Jim Hendry was an old-school guy, and while that might have worked when he first got into the game, modern baseball had passed him, and most baseball management people who feel that way, by. Epstein understands that building an organization from the bottom up, to have everyone do things "the Cubs way" -- even mentioning that there will be a printed manual having this -- is important. But he is also of the belief, as he stated Tuesday, that "every year is a new chance to win", and that bringing in players who care about winning is the way to establish a new mindset.

And he also said, perhaps most importantly, "If you think you know everything about this game, you get humbled pretty quickly." That's an excellent thing to admit, from someone who has been as successful as Theo Epstein has been. He clearly knows a lot about how to win -- but acknowledges he can always learn more.

There are no guarantees for the Cubs, who aren't anywhere near the team the Red Sox were when Epstein took them over after the 2002 season. Boston had five straight winning seasons going into 2003 and had made the playoffs twice in that span. While the Cubs have a pair of playoff years in the last five, their last two years have been quite poor and both the major league roster and farm system need quite a bit of work.

Nevertheless, through good scouting and metrics, Epstein built that kind of organization in Boston, and spoke almost wistfully of "all the families" he made happy when the team finally broke its World Series drought in 2004. It's not too much of a stretch to say that winning in Chicago might make the Red Sox celebration look like the proverbial church picnic.

Epstein summed it up well when he said, "It will be a lot of work. We are ready and hungry. It's not because of one person, it's because of all of us."

It will take a strong organization, top to bottom, to bring the World Series to Wrigley Field. As I wrote above, there are no guarantees, but Theo Epstein appears to be the person, via his background and experience, to do that. If he can, he might not just make the Hall of Fame, they might even name it after him.

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