Oct 24, 2013, 08:49AM

Theo Epstein's World Series Nightmare

A long winter for the Cubs’ leader.

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The 2013 World Series matchup of the St. Louis Cardinals vs. the Boston Red Sox features two of baseball’s more storied franchises and annoying fan bases. Between the Cardinals faithful droning on about being the “best fans in baseball” and their Boston counterparts serenading us with “Sweet Caroline” in the seventh inning stretch, World Series viewers will feel dirty in the morning. It beats having the insufferable Yankees in the Fall Classic but not by much. But if you think this World Series is going to annoy the holy hell out of you just imagine being in Cubs’ President of Baseball Operations Theo Epstein’s shoes.

Cardinals vs. Red Sox is Epstein’s worst nightmare. It’s everything he wants to be versus everything he used to be. As Chicago searches for a new manager, and a winning record, Epstein’s lasting image of the 2013 season will be either the rival Cardinals or his former employers celebrating with champagne showers.

The Cardinals are no doubt baseball’s model franchise—never mind their sloppy play in last night’s 8-1 loss to the Sox. They simply plug and play talent from the minor leagues and generally shrug at free agent departures. The loss of Albert Pujols to the Angels wasn’t such a loss after all. St. Louis spent some of the Pujols savings to ink playoff legend Carlos Beltran (day-to-day after injuring his ribs last night), used the compensation pick to draft budding ace Michael Wacha, and turned over first base to a pair of homegrown sluggers in Allen Craig and Matt Adams. When Beltran leaves this offseason for a big payday with the Yankees or Tigers or some other free-spending team desperate for postseason glory the Cardinals will simply move Craig to right field and carry on. It’s the Cardinals Way; just ask a St. Louis fan, they’ll tell you all about it.

The Red Sox rode some risky decision-making: ditched diva manager Bobby Valentine, improved starting pitching, and had a huge dose of good fortune to get to the World Series for the third time in 10 years. Epstein didn’t leave his hometown club on the best of terms but he is responsible for drafting and developing some of the key components of Boston’s on-field excellence. Epstein no doubt takes pride in the success of former underling and current Red Sox GM Ben Cherington but he may not feel so warm and fuzzy towards the team’s management: principal owner John Henry, Larry Lucchino and Tom Werner.

A Boston victory over St. Louis would be bittersweet for Epstein. He’s partly responsible for crafting the roster, culture and front office hierarchy of the Red Sox but left after several high-priced forays into free agency backfired and Terry Francona was left holding the bag. A victory for St. Louis would create an even greater chasm between the Cardinals and Epstein’s Cubs. With Joe Girardi already inked to a new deal in the Bronx, Epstein is not having a good month. My advice to Theo would be to skip the World Series. Head out to Arizona and watch Kris Bryant launch moon shots into the desert and Albert Almora chase down long fly balls, settle on a new skipper from the Brad Ausmus, Rich Renteria, Dave Martinez group, and spend the next few months avoiding calls from Robinson Cano’s agent.

Epstein’s last few seasons in Boston, and two years of watching the Cubs-Cardinals rivalry up close, should provide ample evidence that there are no quick fixes in baseball. If the Cubs want to be the type of self-sustaining baseball machine like the one in St. Louis it will take years of drafting, developing, and trusting the people and processes in place. The Cubs aren’t close to competing for a World Series title but they do have the right people making the baseball decisions and that’s a damn good start.

—Follow Dan Soderberg on Twitter @dadstimeout

  • I doubt Epstein is very concerned with who wins the World Series. Yes, he drafted and developed many of the players on the Red Sox, but this is Ben Cherington's team. 2012, on the other hand, was Epstein's. Just as the '03 team really belonged to Dan Duquette and the '04 team was Epstein's. Epstein may have drafted the core of the 2013 club (with Cherington's help, of course), but Cherington surrounded the core with his guys. Victorino, Gomes, Napoli, Koji (!), Breslow, Dempster (kidding). These players are the reason the Sox are in the series. Also, Wacha is not a budding ace. Everyone has been saying that recently because he's had three great postseason games. Since when are three games an indicator of future greatness. Don't get me wrong, Wacha is good, and I would love to have him, but in the words of Keith Law, "[he] could end up as a solid mid-rotation guy if that curveball gets just a little bit sharper."

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  • Wacha is pitching like an ace on the biggest stage. Who knows, or cares, what he'll do next year. He's on one helluva roll and at this point he's already been worth the first round selection if he never wins another game.

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  • I seriously doubt the St. Louis front office will think Wacha's draft was "worth it" if he never wins a game.

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