Now, a 37-year-old Yale graduate, who knows something about dealing with great expectations, will take over the Cubs, who haven't won a championship since 1908 -- the longest drought in professional sports.
Theo Epstein will formally be introduced as president of the Cubs' baseball operations at an 11 a.m. CT news conference on Tuesday at Wrigley Field, live on MLB.com. He agreed to a five-year contract, reportedly worth $18.5 million. Cubs fans are already putting bottles of champagne on ice.
Epstein got a head start Monday at Wrigley Field. He went to lunch with some of the Cubs' baseball-operations staff at a restaurant near the ballpark, Vines on Clark. Among those who accompanied him were interim general manager Randy Bush, player development director Oneri Fleita, baseball information manager Chuck Wasserstrom, traveling secretary Jimmy Bank, statistical analysis manager Ari Kaplan and baseball operations director Scott Nelson.
Epstein's first deal will essentially be for himself. When the Cubs and Red Sox announced on Friday night that Epstein was resigning as Boston's general manager, compensation had not been determined.
He will pick up negotiations with Ben Cherington, Boston's assistant GM who will be promoted to the top job with the Red Sox on Tuesday. Both teams will hold news conferences at their respective ballparks then to introduce their new front-office staffs.
If no resolution is reached between the Cubs and Red Sox by Nov. 1, Commissioner Bud Selig said he will get involved. The Red Sox are entitled to compensation because Epstein had one year remaining on his contract.
"They have until Nov. 1 -- Theo and Ben and all the parties involved," Selig said on Sunday night in Arlington, Texas, where Game 4 of the World Series was played. "Hopefully, they can get things done. I always encourage clubs to try to get things done between themselves. Somehow, the Commissioner has enough things of controversy [to deal with].
"They'll either get it done or they won't. If they don't, then I will."
Epstein is expected to reunite his old Boston band in Chicago. The Cubs received permission from the Padres to talk to GM Jed Hoyer about also relocating to Chicago. Epstein and Hoyer joined the Red Sox staff in 2002, and led the team to two World Series championships in 2004 and '07. Hoyer would be named the Cubs' GM, their 14th since 1934. Epstein also reportedly wants to bring aboard Jason McLeod, who was the Red Sox scouting director, and is currently the Padres' assistant GM.
Epstein will be given more of a chance than E.R. "Salty" Saltwell, who was head of concessions at Wrigley Field when tapped by owner P.K. Wrigley to be the GM in 1976. Saltwell lasted one losing season. Epstein can only hope for an extended run like Jim Gallagher, a sportswriter for the Chicago Herald-American. Wrigley challenged him to back up his words, and Gallagher was GM from 1940-49. That stretch included the Cubs' last trip to the World Series in 1945.
The addition of Epstein, Hoyer and McLeod will result in a realignment of the front office under Cubs chairman Tom Ricketts, who wanted someone to take over the team and not only develop players from within but also a winning culture.
Neither Epstein nor Hoyer played in the big leagues, like former Cubs GMs Dallas Green or Ed Lynch. The bombastic Green charged into Wrigley Field after the 1981 season, and in '84, the team won its division and made its first trip to the postseason since 1945.
The Cubs did reach the playoffs again in 1989, '98, 2003, '07 and '08 -- the latter three trips under GM Jim Hendry, who was dismissed in August. But now, they are coming off back to back fifth-place finishes in the National League Central. Epstein has some work to do.
Does he keep manager Mike Quade? Quade is under contract for 2012, but wasn't able to pick up where he left off in 2010 -- when the Cubs went 24-13 after he took over for Lou Piniella. Hitting coach Rudy Jaramillo, bench coach Pat Listach and bullpen coach Lester Strode also have contracts for next season. If Quade goes, does Epstein hire Ryne Sandberg? The Hall of Famer, who managed the Phillies' Triple-A team this season, was not added to the Phillies' big league coaching staff for '12.
Carlos Pena and Aramis Ramirez combined for 54 homers and 173 RBIs, and both will be free agents. Does Epstein bring the corner infielders back? Ramirez, 33, who has a mutual option for 2012, has said he wants a multi-year deal.
What do you do with Carlos Zambrano? The volatile pitcher has apparently been talking to new Marlins manager Ozzie Guillen, and would seem a perfect fit there. But Florida most likely does not want to pick up the $19 million owed Zambrano next year. The Cubs' starting pitching needs help. Losing Andrew Cashner and Randy Wells to injuries after their first turns in the rotation this year revealed the lack of depth in the system.
The Cubs have payroll commitments of $72.6 million for 2012, including $19 million for year No. 6 of Alfonso Soriano's eight-year contract. Remember, Epstein did deal Manny Ramirez to the Dodgers.
When Epstein joined the Red Sox in November 2002 at the age of 28, he inherited a team that won 93 games. In his first offseason, he signed David Ortiz and Bill Mueller and added Bronson Arroyo and Kevin Millar. The Red Sox ended an 86-year wait when they won the World Series in '04.
He's had some missteps with free-agent signings such as Matt Clement, Edgar Renteria, Julio Lugo, Bobby Jenks, John Lackey, and, possibly, Carl Crawford. But the Red Sox also developed their own players, such as Jonathan Papelbon, Dustin Pedroia, Jacoby Ellsbury and Clay Buchholz. Epstein is not afraid, which he showed in July 2004 when he traded popular shortstop Nomar Garciaparra to the Cubs.
In the week since he agreed to the Cubs' offer, Epstein most likely has put together a "to do" list of his own, evaluated what's in the system, who is on the baseball-operations staff. On Tuesday, Cubs fans will get their first look at the new guy.
Carrie Muskat is a reporter for MLB.com. Muskat writes a blog, Muskat Ramblings, and you can follow her on Twitter@CarrieMuskat. This story was not subject to the approval of Major League Baseball or its clubs.