The two met three more times during the season to finalize details, and on Wednesday, Ricketts announced a new five-year extension for Epstein, who has guided the Cubs from a 101-loss team in 2012 to a 101-win team this year with five games left to play.
"It's everything I could have asked for," Epstein, 42, said. "There's no place I'd rather be. I think I said five years ago, it's a great day to be a Cub, and I still feel that way. I still envision feeling that way for the foreseeable future."
Epstein was given the opportunity to totally rebuild the Cubs' organization, and did so, bringing in several of his Red Sox staff, including general manager Jed Hoyer and player development and scouting director Jason McLeod. Both Hoyer and McLeod are expected to receive contract extensions as well.
"We had some good pieces and we had some good players in the beginning, but the organization itself was not in a position where you could believe there was sustainability and consistency and success on the field," Ricketts said, sitting in the visitors' dugout at PNC Park before the Cubs faced the Pirates.
"Obviously, Theo and the guys he brought with him five years ago took the organization down to the studs and started rebuilding," Ricketts said. "I give a lot of credit to Theo and Jed and everybody on that team, but I also give a lot of credit to all of our fans who basically heard our story, listened to us throughout. I think the time and energy to do it the right way has paid off with a team that should be successful for years to come."
Epstein has emphasized the need to build a foundation for sustained success, and the Cubs now have a young core of players to build on. Under Epstein, the Cubs were 61-101 in 2012, 66-96 in '13, 73-89 in '14, and 97-65 last year, earning a Wild Card spot and advancing to the National League Championship Series.
This year, the Cubs won the NL Central in convincing fashion, and they have reached 100 wins for the sixth time in franchise history and first time since 1935. They will finish the year with the best record in the Major Leagues.
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"I see this contract and show of faith from the Ricketts [family] in me as a validation of everybody," Epstein said. "The contract is a product of all the hard work that literally hundreds of people have performed to make this a healthier, better baseball operation."
When Epstein left Boston to take on the challenge of rebuilding the Cubs, who have not won a World Series since 1908, the longest championship drought in professional sports, he talked about how the change came at the right time in his life.
"When you're in one place for 10 years and have some success, pressure builds and things get more complicated sometimes," Epstein said. "The more success you have, the bigger things get and sometimes the heavier the burden as well. Just given my personality, I felt like a new challenge would help me restore my passion and my spirit for the job, and being able to start anew and build something from the ground up was really appealing to me.
"This has been a wonderful environment in which to work, in which to build, in which to make great new friends and stand shoulder to shoulder with some amazing people from the top to the bottom of the organization, as we try to accomplish something that has a lot of meaning to all of us in the organization. I'm thrilled with the decision, I'm thrilled with how things have gone."
One of the key moves Epstein made was to hire Joe Maddon as manager, and the Cubs could average 100 wins in his two seasons at the helm.
"It's a feel-good story," Maddon said of Epstein. "He's earned it, he deserves it."