Theo Epstein says he lost patience

While he was adamant that he was proud of his overall body of work with the team, former Boston 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," Epstein said in an interview with Boston sports radio station 98.5 The Sports Hub.

The result of "giving in to 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," said Epstein, now the president of the Chicago Cubs. "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."

Current Red Sox GM Ben Cherington acknowledged Thursday that the give-and-take struggle between baseball and business still exists.

"I think Boston is like some bigger markets in baseball, where expectations are going to be high every year and along with that the business are different than they might be in a different city," Cherington told Boston sports radio station WEEI. "In places like that, and certainly Boston is one of those, the success of the team on the field is the gasoline that runs the engine of the business and the business needs to run to then pay for that team on the field. There needs to be a symbiotic relationship between the baseball side and the business. And we need to have that here.

"In any relationship like that, there needs to be collaboration, but with collaboration sometimes there are necessary pushbacks. The business side should challenge baseball operations and baseball operations should challenge business side. There are some decisions baseball operations just makes on our own. There are others we collaborate on. Ultimately it's up to us to execute on the decisions we make."

During the last two offseasons of his 10-year tenure as Red Sox general manager, two big free-agent signings by Epstein now stand out as albatrosses: pitcher John Lackey (five-year, $82.5 million deal) and outfielder Carl Crawford (seven years, $142 million).

When specifically asked by The Sports Hub about the Lackey signing, Epstein spoke mostly in generalities about the right-hander -- who is 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 done in one offseason just because of what's going on in the environment around you."

Epstein, whose 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 says he thinks the struggles of this year's Red Sox are in large part because of 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 received better outings from their rotation as of late, the team entered Wednesday night with a 4.87 ERA from its starters this season, 12th out of 14 teams in the American League.

"We're not building a team in a vacuum here," Cherington told WEEI. "In the end, building winning teams, that is the best recipe for the baseball business in Boston. It's our job in baseball operations to go execute that. Every decision has a short, medium and long-term impact. It's our job to balance all those things."

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."