When he took over as the Red Sox general manager in November 2002 at 28, Epstein inherited a team coming off a 93-69 season and second-place finish in the American League East. He had Pedro Martinez and Derek Lowe, both 20-game winners in '02, a team that ranked third in the AL in ERA, second in batting average, eighth in fielding percentage.
In Boston, Epstein said he wanted to improve the player development. He also made shrewd moves. He signed David Ortiz to a $1.25 million contract, added Bill Mueller and Kevin Millar. Ortiz finished '03 as an MVP candidate, Mueller won a batting title and Millar provided clutch hits and contributed to clubhouse chemistry. In 2003, the Red Sox won the AL Wild Card and lost to the Yankees in a seven-game AL Championship Series.
The next year was magical, as the Red Sox ended an 86-year wait and won the 2004 World Series.
The Cubs have been waiting since 1908 to celebrate a world championship, and Ricketts is banking on Epstein leading the way.
Both the Cubs and Red Sox play in neighborhood ballparks loaded with more charm than state-of-the-art amenities. Both teams have a rabid fan base, play in large markets and rank among the top in terms of payroll.
But the Red Sox had Nomar Garciaparra, Jason Varitek, Manny Ramirez and Johnny Damon when Epstein arrived. The Cubs are coming off back-to-back fifth-place finishes. As of now, the roster doesn't include a starting first baseman or third baseman, unless you count prospects Bryan LaHair and Josh Vitters. Right field is wide open. The pitching has more questions than answers. The fielding was the worst in the National League.
Welcome to Chicago, Theo.
"I was ready for the next big challenge," Epstein said when officially introduced on Oct. 25.
That's what Ricketts was hoping for, and one of the reasons he offered Epstein the title of president of baseball operations, not general manager.
"It was my gut feeling that after everything he's accomplished in Boston, this would be the next great challenge for him, so we just had to go with the gut and hope it would come through," Ricketts said about calling the Red Sox for permission to talk to Epstein.
Ricketts interviewed Epstein at a neutral site, somewhere between Boston and Chicago.
"Within a few minutes of talking to him, I had a good feeling that this was the right guy for us," Ricketts said. "Obviously, the track record is terrific, the recommendations that I got from people in the industry were terrific.
"I wanted to make sure it was a person who I felt I could work with. You can tell in a short period of time. When he came in, he's very low key, very thoughtful, very team oriented -- all the things I thought would be great, not only for the baseball side, but for building a great baseball culture. It just all kind of fit."
Epstein was given the chance to create his dream team in the front office. He's reunited several members of the Red Sox's staff who helped him, including GM Jed Hoyer, scouting and player development director Jason McLeod and assistant Shiraz Rehman.
Ricketts was willing to give Epstein the higher status and add to the Cubs front office.
"I did see he had a comment to one of the papers toward the end of August about moving on that he'd like a bigger title," Ricketts said. "I was open-minded. I was like, 'It made sense -- we'll bring him in as president of baseball and everything flow up to him and he can build his own team underneath him.' I was comfortable with that."
If Epstein thought Red Sox fans were hungry for a World Series championship, he now faces a fan base that's riding the longest championship drought in professional sports.
"I'm not saying the timetable is immediate," Epstein said. "Over time, we'll get this thing done. It's not going to happen overnight. But we'll take every opportunity to win seriously."
When he took over the Red Sox, Epstein pledged to transform the team into a "scouting and player development machine." During his introductory news conference with the Cubs, he vowed to build "a foundation of sustained success," which begins with a commitment to the Minor League system.
The rule changes with the new Collective Bargaining Agreement may alter what the Cubs can do in the future. They spent $12 million in the 2011 June First-Year Player Draft, a huge change from the previous two years, when they spent $8.7 million combined.
Epstein is not afraid to make changes. The Red Sox roster at the end of 2003 had 17 players who were not on the team the previous year, and nine of those were not even in the organization when the season began. But the Cubs' and Red Sox's situations are not similar.
"It's unique," Epstein said of the Cubs. "Boston's not Chicago, Chicago's not Boston. Every city, every market has its own personality, its own idiosyncrasies. I don't pretend to understand them all yet.
"Having grown up in Boston, I have a better feel for that market. I'm a baseball fan. When I was with the Padres, I'd come through Chicago and we'd go through Wrigley Field and play the Cubs. I got a sense of what things were like here."
Does he? Epstein was surprised by a fan who recognized him at a Starbucks when he was in Chicago to look for housing. It didn't take long for "Theo-logy" T-shirts to appear around Wrigleyville.
Hiring Epstein was the biggest decision the Ricketts family has made since deciding to purchase the Cubs, a sale completed in October 2009. But Ricketts didn't expect the intensity of "Theo mania."
"As a Cub fan, I'm excited, and I expect other fans to be excited," Ricketts said. "I was a little surprised at the amount of excitement in general, but it's all good. People should be confident we have a really good baseball team, a good front-office baseball team, and they're going to make the right decisions to win next year and make those decisions without sacrificing something down the line [to build a foundation for sustained success]."