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NESN Debates: Will Theo Epstein Lead Cubs to World Series Within 10 Years?

Editor’s note: Each week, two members of NESN.com’s editorial staff will debate a topic via email in a feature called “Field Judges.” After reading both sides of the argument, NESN.com readers can give the final say by voting below.

Theo Epstein became the president of baseball operations with the Chicago Cubs this week. It comes nine years after he was introduced as Red Sox general manager, an announcement that came with much less fanfare than his news conference Tuesday in Chicago did. 

Epstein was introduced in Boston as a relative unknown before ascending to the status of a local legend after guiding the Sox to a world title in 2004 and then another in 2007. He’s no longer a relative unknown, and he heads to Chicago with many hoping he can be the savior the Cubs need to end a century-long title drought.

Never mind winning the club’s first World Series since 1908. If we give Epstein 10 years in Chicago, can he get the Cubs to their first World Series since 1945? Assistant Editors Mike Cole and Ricky Doyle will battle this one out in NESN Debates.

Cole: OK, Rick. We know what Theo Epstein is capable of when he’s put in a position to win. He came in to Boston, and within a couple of years, he was exorcising 86 years of demons with a fat 2004 World Series champions ring. Can he play Ghostbuster in Chicago? Since you’re younger, and I’m also better looking, I’ll defer to you for the first shot here. Have at it.

Doyle: I believe you mean “phat” –- with a p-h. Either way, thanks for bringing this question up, because it will allow me to have my response on record for when my prediction comes to fruition. While I hate buying into the hype, I can’t help but do so. Steve Bartman, get your arm loose, because within the next decade you’ll not only be able to come out of hiding, but you’ll be throwing out the first pitch at Wrigley Field — a la Bill Buckner at Fenway in ’08. There’s work to be done in Chi Town, and it’s going to be a difficult process, but: In Theo The Cubs (and I) Trust.

Cole: As a certain Boston sports radio personality would say, “You’re making my point.” There is work to be done in Chi Town –- and a lot of it. At this rate, Epstein has a better chance of fixing the economic mess this country is in than bringing the Cubs to the World Series. He inherited a team in 2004 that was already built. Sure, he put on some of the finishing touches (David Ortiz, Curt Schilling, Keith Foulke, Dave Roberts, Doug Mientkiewicz), but he doesn’t have that immediate luxury in Chicago. They haven’t won more than 83 games in the last three years. They have some real bad contracts. And their farm system isn’t necessarily anything to write home about.   

Doyle: Wow, those are some really nice “finishing touches.” Look back at that ’04 season once again and you’ll see how big of a role each of those guys played in bringing a title to Boston, particularly the first four. I’d argue Ortiz and Schilling might have even been the two most important players of that playoff run, and you couldn’t have asked for more from Foulke (one earned run in 14 innings in the playoffs). As far as the Cubs having some bad contracts, we might be overstating that a bit. Alfonso Soriano is signed through 2014, which is obviously tough, but Carlos Zambrano’s contract is up after next season. And it’s not like we haven’t seen the Red Sox put up some wins throughout Theo’s tenure while being plagued with some poor contracts.

Cole: Zambrano actually has a vesting player option according to Cots. If he finishes in the top four in Cy Young voting in 2012, it will kick in and he’ll make almost $20 million — so there’s that. But again, your response is right up my alley. You can’t argue the fact that the Sox didn’t win a playoff game from 2008 under Epstein. Now, that doesn’t take away from the World Series titles, but I do think it plays to a certain “inability” to gauge free agents and their potential impacts. The track record, particularly toward the end of his Boston tenure, doesn’t lie. Until he proves that he can buy the right talent, I’m not buying his chances of turning around a rather hapless franchise. 

Doyle: You have a better chance of seeing Cy Young himself pitch a game in 2012 than Zambrano finishing in the top four. And while I understand Theo made some lackluster free-agent signings throughout his tenure, particularly toward the end (although I’m not ready to write off Carl Crawford like a lot of people have already), I’m encouraged by what he’s going to bring to the table in terms of player development. And I think that’s just as big of an issue for the Cubs right now.

As you mentioned, their farm system isn’t anything to write home about, which is going to handcuff Theo from the start because he won’t be able to be as bold on the trading market as he was during his early years in Boston. But you can’t deny the success the Sox had in drafting players throughout Theo’s tenure. It included players that helped the Sox win a World Series and players that helped yield a solid return. I have no doubts that he can help do the same in Chicago.

In other words, I said he’ll help bring a World Series to Chicago within the next 10 years, not next year

Cole: Your point on the farm system is well-taken, but  don’t be too quick to write off the fact that there are a lot of scouts and the sorts that won’t be joining him on the North Side.

I still don’t think the Cubs will be in the World Series in the next decade. That said, I do think the Cubs will get better, and there definitely is plenty of room for improvement.

However, all bets are off if Theo is lucky enough to have a gift like this fall into his lap.

Doyle: You’re absolutely right about that. But I know one executive who will be joining him, Jed Hoyer. The same Jed Hoyer that worked alongside Theo for both World Series titles. And also the same Jed Hoyer that, along with Ben Cherington, helped land Josh Beckett and Mike Lowell — as you probably recall, two of the biggest components of that ’07 title.

So, yes, I agree there’s more that went into those two Sox titles than what immediately meets the eye. But given Theo and Jed’s reputation, and the fact that the Cubs do have ownership committed to fielding a winner (willing to spend cash, etc.), I feel like the wheels are finally in motion for some October glory for these Cubbies … with or without Henry Rowengartner and 700 innings from Chet Stedman.

Will Theo Epstein lead the Cubs to a World Series within 10 years?