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How Theo Epstein can bring a long-awaited title to the Cubs

It appears that the Chicago Cubs are going to pry away Theo Epstein from the Red Sox to be their new general manager. Epstein, 37, was the face of the new breed of ultra-young GMs, handed the reins of the Red Sox in 2002 and producing two World Championships in nine seasons as their top executive. His 2004 team became the first Red Sox club since 1918 to win a World Series, assuring that he'd never need a wallet in any New England bar for the rest of his life.

Now his move to Chicago, which comes on the heels of the Red Sox' late-season collapse, the departure of manager Terry Francona and some vicious press coverage of both, gives Epstein a chance to be a hero to the game's other long-suffering fan base. The Cubs and Epstein have agreed on the details of a new contract; it's just a matter of the Cubs and Red Sox agreeing on player compensation for a GM who was signed through next year.

Once the deal is finalized, Epstein will inherit a much different situation than he did in 2002, when the Red Sox promoted him to be their general manager. Epstein got his job months before the release of Moneyball by Michael Lewis, when there were still substantial gaps in the information teams used and how they used it. Epstein would exploit this to add players such as David Ortiz, Kevin Millar and MIke Timlin at low cost. He inherited a stronger core of talent there, with Manny Ramirez, Nomar Garciaparra, Johnny Damon, Pedro Martinez and Derek Lowe all at or near their primes. The Sox farm system held future stars such as Hanley Ramirez, Kevin Youkilis and Jon Lester, as well as many others who would go on to decent MLB careers -- most of whom were used by Epstein as trade bait to bolster the roster.

The current Cubs don't offer all that. This team is older, with more dead money and less building-block talent than the Red Sox had nine years ago. There's no one at the level of Ramirez or Martinez in this organization, and really, there are perhaps two, maybe three championship-caliber players to be found. The first is Starlin Castro, a 21-year-old shortstop coming off a season in which he led the NL in hits. He's raw, prone to silly mistakes in the field and silly swings at the plate, but Castro is, based on age, position and skill-set, one of the most valuable properties in baseball.

Epstein also inherits a good No. 2 starter in Matt Garza and a strong, if erratic, reliever in closer Carlos Marmol. There are some prospects here, if nothing the caliber of Lester and Youkilis. Outfielder Brett Jackson -- who is one of the players rumored as compensation for Epstein's services -- could step into rightfield next year. Bat-first catcher Wellington Castillo may push incumbent Genovany Soto aside as soon as 2012. There are some hard throwers who could improve the bullpen next year, like Chris Carpenter and Andrew Cashner, as well as talent buried deeper in the system like 2011 first-round pick Javier Baez and sixth-rounder Neftali Rosario. The rest of the roster consists of players in their 20s who are not good enough (Tyler Colvin, Darwin Barney, Randy Wells, Jeff Samadzija, Soto) and players in their 30s who are not young enough (Marlon Byrd, Alfonso Soriano, Carlos Zambrano) to build a team around.

In 2003, Epstein could focus on the final 20 spots on the roster because he had a championship-caliber core. Here, he almost has to start over around Castro, Garza and a crop of nearly-ready players who don't have superstar upside.

Then again, there are some advantages. First of all, the Yankees don't play in the NL Central, and for that matter, neither do the Rays. If you could place teams on some absolute scale of quality, the level you need to reach to be successful in Epstein's new division is lower than what he needed to reach in the AL East. In the nine seasons Epstein was in Boston, seven NL Central teams outscored their opponents by at least 100 runs; just two have done so in the last six seasons. In that same time, 17 AL East teams have turned the trick. The AL East had as many +100 teams this year as the NL Central has had in the last six. The job of winning the division is simply easier running the Cubs than it is the Red Sox.

Epstein is also escaping one of the few teams that may have more bad contracts than do the Cubs. It's his own doing, of course, but the staggering amount of money due Carl Crawford, John Lackey and Daisuke Matsuzaka -- all of whom were lousy, injured or both in 2011 -- may tie the Sox' hands in the short term. Throw in megadeals for currently productive players like John Beckett and Adrian Gonzalez and it's not hard to see even John Henry saying, "Uncle," before reaching into his pocket for the next big free agent or trade acquisition. The Cubs are, famously, saddled with bad contracts for Alfonso Soriano ($57 million through 2014) and Carlos Zambrano ($19 million in 2012), but the load is lighter and only Soriano and Marmol ($9.8 million in 2013) are signed past '12.

The Cubs also have revenue -- and therefore payroll -- upside that the current Red Sox may have reached. According to USA Today's salary database, in 2002, the year before Epstein arrived, the Sox' payroll was $108 million. It was $161 million in 2011. The Cubs were at $125 million last year, so there's room for growth for a team that is a tentpole franchise, the most popular one in a two-team town, with an icon of a ballpark and access to tremendous local-media revenues. Like the Red Sox nine years ago, the Cubs are a team the locals want to love, and baseball fans around the country want to get behind -- and when they succeed, the money will pour in and be used to further the team's success.

You don't make it all happen in one offseason, of course, but once Epstein is putting salads on his hot dogs, having pop with them and reacquainting himself with the letter "r", here's what he should be doing to put the Cubs on the path to their first National League pennant since 1945 and their first World Series title since 1908:

1. Fielder, not Pujols. Albert Pujols is the better player of the two, and as he's shown in this postseason, his advantages on the bases and in the field over the younger Prince Fielder are substantial. For the Cubs, though, there are two strong reasons,among others, to favor Fielder. One, they already have a very old roster, and adding a 32-year-old, even a great one, adds to their risk profile. Two, they could use a left-handed bat, as only Jackson among their projected 2012 and '13 starters swings from that side. Pujols' huge run down the stretch also means he may be the more expensive of the two players, so chasing Fielder could be slightly less costly. Finally, whereas the Cardinals desperately want and need to keep Pujols, the Brewers seem to have resigned themselves to losing their slugger, so it may be easier for the Cubs to spirit him away. The Cubs need to pick one of the two and target him -- Fielder is the better play.

2. Not at Wrigley, Carlos. Carlos Marmol has peaked early, as many max-effort short relievers do. Nonethless, he's due nearly $20 million through 2013, and he's a replaceable talent -- especially for an organization whose strength at the moment is in live arms. Epstein should move Marmol to a team whose bullpen was a big part of its failure in 2011, playing up the righthander's strikeout and save totals. The return in a deal like this isn't as important as moving the overpaid player to free up money for better use, but possible destinations include Boston (Marmol as compensation for Epstein, or for one of the Red Sox' two third-base prospects, Will Middlebrooks or Kolbrin Vitek?), the Angels (who had a big falloff after rookie Jordan Walden) or the Mets (who enter the offseason with no closer and a lot of money coming off the payroll).

3. Don't worry about 2012. The Red Sox won the wild card and came within one run of the AL pennant in Epstein's first year. That may be a bit too much to ask of next year's Cubs, who will still be transitioning out of the Jim Hendry era in 2012. The biggest thing the team can do next year is try to get value for players on their final seasons of deals. Zambrano, Ryan Dempster (assumed to be exercising a player option) and Marlon Byrd are all free agents at the end of the year. All should be given every chance to pick up trade value, even if it means a slight performance hit over the available alternatives. At the same time, the Cubs can use next year to establish Jackson, Carpenter, Cashner and Castillo in major league roles with an eye toward 2013. Pushing too hard to make '12 a big year -- to match the success of the '03 Sox -- isn't sensible based on the talent on hand or what's available on the market.

Let's be clear about this: Theo Epstein is one of the best general managers in the game, and he's going to put the Cubs in position to get back to, and win, the World Series. He surrounds himself with talented people, he is open to both sides of player evaluation -- scouting and statistical analysis -- and he's always willing to improve his own processes. For all the chaos the Red Sox have descended into this month, Epstein spent nine years making that organization a model one, aided by a good owner and a slew of talented assistants. All of that is replicable in Chicago. This move will go down as one of the best in Chicago baseball history, and it will eventually produce a long-elusive World Series championship banner for the Cubs.

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