So who better to enter that caldron of despair than a man who survived it in Boston? Theo Epstein, the general manager who helped the Red Sox reverse their own epic curse dating to 1918, is close to completing his transition from Fenway Park to Wrigley Field.  According to a Red Sox official speaking on condition of anonymity, Epstein is nearing a deal to become the Cubs’ top baseball operations executive. Another Red Sox official said the Boston front office widely expects him to leave.  Multiple reports have said Epstein has a five-year agreement in place with the Cubs, with an average annual value between $3 million and $4 million, which almost certainly would make him the game’s highest-paid general manager. Because Epstein was signed with the Red Sox through 2012, the teams must agree on how the Cubs would compensate the Red Sox.  Epstein, a Boston native who grew up dreaming of a job with his hometown team, was the youngest general manager in baseball when the Red Sox named him to the position in 2002 after Oakland’s Billy Beane turned down an offer from the team. Now 37, Epstein has helped build two champions, in 2004 and 2007, merging traditional scouting methods and modern statistical analysis.  But he would be leaving the Red Sox at a precarious point. The team lost the American League wild-card spot despite leading the Tampa Bay Rays by nine games on Sept. 2. The collapse resulted in the departure of Manager Terry Francona, who resigned Sept. 30, citing, in part, a lack of support from ownership.  John Henry, the Red Sox owner, could have refused the request of Tom Ricketts, the Cubs’ owner, to interview Epstein. Even though Epstein’s new job could include the title of president, Epstein would essentially perform the same role for the Cubs as he has for the Red Sox, as the head of their baseball operations.  But nine years as the Red Sox general manager may have been enough for Epstein, who is married with a young son. While the Cubs clearly have their own rabid fan base, there may be no more intense baseball atmosphere than the one in Boston.  In an interview with the Boston radio station WEEI last week, Henry hinted that Epstein might be losing patience.  “I think there’s a certain shelf life in these jobs,” Henry said. “You can only be the general manager if you’re sane. You can only be the manager for a certain amount of time. Tremendous pressure cooker here — 162 games, it’s a long season and the pressure here is 365 days, so Theo is not going to be the general manager forever.”  Epstein will leave behind a stable baseball operations staff, with his assistant, Ben Cherington, expected to be promoted as his replacement. And as badly as the Red Sox folded in September, their offense did lead the majors in runs this season.  But Epstein also leaves a roster of sour personalities who tuned out Francona and dissolved into clubhouse disharmony down the stretch. Two of the players he signed to lucrative contracts — starter John Lackey (entering the third year of a five-year, $82.5 million contract) and left fielder Carl Crawford (entering the second year of a seven-year, $142 million contract) — have flopped.  Epstein shrewdly acquired players like Keith Foulke, David Ortiz and Curt Schilling for the 2004 championship team, and oversaw the drafting of Jacoby Ellsbury, Dustin Pedroia and Jonathan Papelbon, who starred for the 2007 team. But he also had costly misfires on acquisitions like Matt Clement, Julio Lugo, Edgar Renteria and Lackey.  The Cubs’ roster does not have the same quality core players Epstein inherited in 2002 from his Boston predecessors, Dan Duquette and Mike Port. That team had Johnny Damon, Pedro Martinez and Manny Ramirez, among others, and had just won 92 games. The Cubs were 71-91 this season, and have finished in fifth place in the National League Central in each of the last two years.  Epstein will also find a bloated payroll in Chicago. The 2012 Cubs will have $50 million tied up in three players of minimal value: Alfonso Soriano, Carlos Zambrano and (if he exercises his player option) Ryan Dempster.  The Cubs have won recently, with division titles in 2007 and 2008, but they are not considered a progressive organization in the way they evaluate players and make decisions. Epstein will try to change that, although the Red Sox may limit how many colleagues he can take with him from the Boston front office.  Epstein secured his legacy in New England with the two championships, but his tenure apparently will end with the embarrassment of a team that stumbled to a 7-20 record in the final month of the regular season. Just a few days ago, one person who knows Epstein well said he doubted Epstein would quit under such unhappy circumstances.  “Knowing the way he is, I can’t imagine him walking away from such a failure,” said the person, who spoke on condition of anonymity because Epstein had not authorized him to discuss his future. “He is an extremely competitive person.”  Then again, there are challenges everywhere, and the prospect of lifting the Cubs to glory would be invigorating for any competitive executive. Soon it will be Epstein’s task to soothe many decades of disappointment for one of baseball’s grand old franchises. If previous experience is required for the job, he just might be the perfect fit.
Officials with the Red Sox said they expected their general manager, Theo Epstein, to reach a deal to take over baseball operations with the Chicago Cubs.