As Epstein left Boston and the paparazzi that followed him, he took a lot of criticism for his most recent free-agent signings -- like Carl Crawford, John Lackey and Edgar Renteria -- along with the credit for the only two World Series championships the Red Sox have had since the Woodrow Wilson administration.
Epstein hasn't ducked the free-agent questions, but in the end, his legacy is that he completely changed the organizational philosophy to one dedicated to scouting and the human development of the players they sign. With three of his former assistants assuming general manager roles this week, Epstein left behind an organizational succession that allows Cherington to proceed with a managerial search, trades, signings and the offseason Minor League development with a baseball operations staff in place.
Everyone in the bowling alley in the bowels of Fenway Park known as Baseball Ops knows Cherington has been ready to be a Major League general manager for years. Everyone knows that Mike Hazen, who has ascended from farm director to player development director to Cherington's spot as the No. 2 man, is fully qualified, as well as exceptionally gifted, like Cherington, in people and evaluation skills. Brian O'Halloran is already entrusted with the inner machinations of the Baseball Ops, Ben Crockett is in place as farm director, Amiel Sawdaye is two years and two very good Drafts into the role of scouting director, Allard Baird and Jared Porter are three years into their roles in professional scouting and Craig Shipley, a tremendous evaluator, is nearly a decade into running the Red Sox's international scouting.
Cherington has the autonomy to add scouts and others to the process, and because he has spent enough time in the Yawkey Way office, everyone in the organization is comfortable and trustful. That he and Hazen have come out of the development process, they know the organization players well, be he Ryan Lavarnway or Felix Doubront, J.C. Linares or Josh Reddick or Alex Wilson. Because of the September collapse and the leakage about the workings of the clubhouse, the Red Sox expect to have Josh Beckett, Jon Lester and several others motivated to re-establish themselves above slippages and misconceptions.
There will be an immense pressure on Cherington because Red Sox fans have become what they panned Yankee fans for being -- people for whom anything short of the World Series is a failure -- but expectations in 2012 will be far different from the assumed greatness of '11, a year after which a drop in television ratings prompted the need for a splashy winter.
Does Cherington re-sign Jonathan Papelbon and consider Daniel Bard as a starter? Does he bring back David Ortiz and assume Kevin Youklis can come off two surgeries to play every day at third base? Does Cherington re-sign Jason Varitek or hand the catching job over to Lavarnway and Jarrod Saltalamacchia without the Varitek support system? Who plays shortstop? Can Reddick, Linares and Ryan Kalish be enough in right, or does he make a run at Michael Cuddyer? Who pitches the seventh and eighth innings? Are there a couple of middle-class starters on the market that fit the budget? How does Cherington address some of the conditioning and clubhouse issues?
Those are significant decisions, but they are not the restructuring issues that Epstein, Hoyer and Jason McLeod face with the Cubs. Yes, the Cubs are loveable and all that, but the club's information and technical systems are from the days of their College of Coaches. The farm system is thin, partly because the former owners wanted Jim Hendry to constantly go for it and trade kids for veterans, all the while refusing to allow the scouting department to ignore slot and sign the best players on the amateur market; Epstein has the freedom and wherewithal that Hendry did not have, but the Draft process takes years to build a contending team.
In time, Epstein will build a front office, development, scouting and informational staff comparable to what he developed in Boston. If one works for Theo, one knows that every idea and every report is read, considered and respected.
"It is remarkable the loyalty he commanded in his leadership," Cherington has said, but that will take time in Chicago. If you hung out in the bowling alley with the Baseball Ops folks, you would know that Cherington carries that same loyalty and respect and character, and the seamless transition from Epstein's news conference in Chicago to Cherington's in Boston spoke volumes about what an organization from top to bottom is about.
There was a burnout factor in Epstein's desire to leave, which he was going to do regardless after the 2012 season. It was as if he were stuck on an elevator between the ninth and 10th floors. His wife, Marie, and son, Jack, could not live normal lives. There often was an unmarked Brookline police cruiser at the end of his street because of a stalker and concerns about the family privacy.
But Epstein never stopped trying to build the model he dreamed of when he took over the Red Sox, and more important than the two titles and Fenway Park sellouts, he left the organization to his close friend far, far better than he found it, with a value system that reflects the family structure in which he was raised, a half-mile from Fenway Park.