What is Theo Epstein getting himself into?

What is Theo Epstein getting himself into?
October 13, 2011, 11:40 pm
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Theo Epstein convinced himself that hes ready for the platform that could one day put him in Cooperstown. The only way this ends as a total success is if hes cruising down Michigan Avenue on a float during the championship parade.

Andy MacPhail was a hotshot executive with two World Series rings from his time with the Minnesota Twins, but he never got it done here. Jim Hendry had the Cubs one victory away from the pennant in 2003, and assembled a 97-win team five years later, but he couldnt sustain it.

Dusty Baker and Lou Piniella are two of the best managers of their generation, and both could wind up in the Hall of Fame, but each man was worn out by the end.

Epstein is sold on the challenge, with only the final details to be worked out between the Cubs and Boston Red Sox. The deal will give him almost absolute power over baseball operations for a franchise that hasnt won a World Series since 1908.

But at some point across the next five years perhaps after what Piniella once termed a Cubbie occurrence Epstein will almost certainly pause and think: What did I get myself into?

This is the lay of the land youve inherited.
Take the power back

As baseball czar, you will have to unify a divided front office. There are Hendrys buddies, the numbers guy (Ari Kaplan) hired by chairman Tom Ricketts and the new people Epstein will inevitably bring into the organization. There is a team president (Crane Kenney) who awkwardly inserted himself into baseball matters, but should now be focused solely on business operations.

Fans dont want to read anymore about how ownership instability undercut Hendry, but its foolish to think that it didnt impact the on-field product, and nave to think that freezing the major-league payroll wouldnt have consequences. The Cubs have paid the price after going all in when Tribune Co. had the team up for sale. The worst of it seems to be almost over.

Look in the mirror

Ricketts wanted an adaptable leader, not some slash-and-burn executive who would fire everyone. There are some capable people already in place, but it will be up to Epstein to decide whether Mike Quade is the right manager to lead this team. The Cubs view Ryne Sandberg as having a problem with Hendry not a grudge against the entire organization after being passed over for the job last year.

Bench coach Pat Listach has a presence in the room, and players trust hitting coach Rudy Jaramillo. First-base coach Bob Dernier has institutional memory and good relationships with the young, homegrown players after being a minor-league coordinator. You have a reputation as a good guy to work for, someone respected by the people on the ground. They all deserve answers as soon as possible.

Build an empire

The Cubs were late to the game in the Dominican Republic, and slow to expand their international scouting operations, but they essentially cover the globe now. You have to pour more money into those efforts. Ricketts already gave a four-year contract to vice president of player personnel Oneri Fleita, to maintain a sense of continuity and keep some major projects moving forward.

Even if Fleita doesnt keep the same title or portfolio, he has a valuable network in the Dominican Republic, where the Cubs will soon break ground on a new academy, and family roots in Cuba. Ricketts loves Jose Serra, Fleitas Latin American coordinator, the scout who signed Starlin Castro and the godfather to Carlos Marmol. All the kids Serra scouts want to be the next Castro. You must capitalize on that buzz.

Invest in the future

Roughly 48 hours before the 2007 draft, scouting director Tim Wilken still didnt know exactly which direction his staff could go or how much money would be allocated for their picks. The sale of the team, and the uncertainty at the top of the organization, handcuffed the department. If the next collective bargaining agreement doesnt bring major changes to the amateur draft, you should spend big.

Wilken is signed through 2012 and has been assured by Ricketts that there will be a place for him in the organization next season. Wilken once worked for future Hall of Fame executive Pat Gillick, back when the Toronto Blue Jays were winning World Series titles, and signed Roy Halladay and Chris Carpenter out of high school. Find the next big thing in the draft.

Feed the beast
Hendry went underground when he had to, but he also built up goodwill by talking with the media and telling his side of the story (and a steady stream of off-color jokes). Despite his silence during this search, Ricketts slowly seems to be learning this lesson: You have to be accessible. Otherwise the offhand quotes a guy to watch my baseball guy never go away.

Just like in Boston, the narrative will play out almost 12 months a year. Maybe the local media wont be as obsessed with your personal life, because you didnt grow up here. But all the questions exhausted even Piniella, who came of age in the middle of the New York tabloid newspapers wars, while the Bronx was burning. This wont be a holiday weekend on Marthas Vineyard.

Act in cold blood

As much as Ricketts appears to be committed to player development, the chairman really finds comfort in numbers. He wants data to drive more decisions. Hendrys interpersonal skills enabled him to close deals and bring in talent, but he sometimes got too close to the players. Then again, you made some of the same mistakes with free agents.

This could mean fewer no-trade clauses, holding off on the extra year tacked onto the contract, perhaps telling Aramis Ramirez to find a multiyear deal elsewhere. If you have any questions about the office politics and turf battles to come, you can always call Hendry, who thought highly of your work in Boston.

Soon it will be time to build a new machine here in Chicago.