Theo reflects on his time with Red Sox

While he was adamant that he was proud of his overall body of work in Boston, former Red Sox general manager Theo Epstein acknowledged Wednesday that late in his tenure he veered from the philosophy of patience he helped to instill in order to try to win immediately.

“Some of the offseasons that we had were more offseasons of convenience -- giving in to the need to be good next year,” said Epstein, who was a guest on Boston sports radio station The Sports Hub on Wednesday afternoon (listen to the interview HERE).

The result of “giving into that monster,” as Epstein put it, was spending big in free agency when it might have been more prudent to stay patient.

“It’s a natural push and pull that exists in any sports organization,” Epstein explained. "When you are in a big market and then you win, and you’re up against the Yankees, and ratings are what they are and attendance is what it is, no one wants to go backwards, as a business, you don’t want to go backwards. …

“Sometimes on the business side it’s important to sort of have something with some sizzle in an offseason. It’s the baseball operations department’s job to push back against that, just as it’s the business side’s job to sometimes advance those thoughts. It’s my responsibility if we got out of whack. And then you could always execute better, too. … we didn’t execute well in big name free agency.”

Over the last two offseasons of his 10-year tenure as general manager of the Red Sox, two big free-agent signings stand out as albatrosses: John Lackey (5-year, $82.5 million deal) and Carl Crawford (7 years, $142 million).

When specifically asked by The Sports Hub about the Lackey signing, Epstein spoke mostly in generalities about the pitcher -- who is currently recovering after Tommy John surgery -- but did shed some light on the environment around the team at the time of the signing.

“If I have a regret about the way we handled that offseason (after the 2009 season), it was that instead of being more patient and saying ‘We’ll strike when the time is right,’ there was a lot of pressure in the environment at the time to do something,” Epstein said. "If I learned a lesson from the offseason it’s never feel the need to do something. If you’re trying to avoid one move that you don’t think is going to work out, don’t then settle for a different move that maybe doesn’t check all the boxes. Be true to the philosophy and understand the bigger picture. There’s always another day to fight, you don’t have to get everything one in one offseason just because of what’s going on in the environment around you.”

Epstein, whose Chicago Cubs will host the Red Sox this weekend at Wrigley Field, said he was most proud of the organizational philosophy he helped instill in Boston and his work in player development and the draft.

“I can look the people I worked for in the eye and know that we did really well,” Epstein said. "It wasn’t perfect but we won a couple of World Series, changed the franchise for the better. We left a real foundation of scouting and player development, a lot of great people in place to continue that work and left a lot of talented young players who are serving the team well and will continue to do so.”

Epstein said he thought the struggles of this year’s Red Sox team were in large part due to injuries, but also acknowledged a team can go through periods when players you have come to count on -- in particular, pitchers -- will struggle.

“If multiple starting pitchers underperform at the same time, it’s always going to leave you in a stretch where it’s hard to play better than .500 baseball,” Epstein said.

While the Red Sox (30-32) have gotten better outings from their starting pitchers as of late, the team still has a 4.87 ERA from its starters this season, which ranks 12th of 14 teams in the American League.

As for his first season as president of the Cubs, Epstein says he is “putting an emphasis on the long term” as he starts the rebuilding process for a struggling club that is just 21-40, deeply entrenched in the NL Central cellar.

“We’re at a different point in the evolution of this franchise,” he said. "We’re having to start some things from the ground level and build up. It’s going to be a bit of a longer process.”