Theo's 'monster' now haunts Ben

Although Theo Epstein is on to a new city, a new team and new problems, his impact is still being felt in Boston -- and will be for years to come.

The former Red Sox general manager helped bring two World Series titles to Boston, built the farm system from the ground up and instilled a culture of winning that wasn't present before him. But he also leaves behind some bad contracts, free-agent signings that he acknowledges were a deviation from the core principles of patience and self-reliance he helped introduce.

Epstein admitted as much in a series of interviews he conducted as his Cubs prepared to host the Red Sox for a weekend series at Wrigley Field.

We're glad he got it off his chest. The fact remains, however, that Theo "giving in to that monster" of the team's win-now business culture is now Ben Cherington's problem.

Exhibits A and B in the case against Theo are John Lackey and Carl Crawford, whose free-agent contracts signed during the last two offseasons of Epstein's reign have yet to pay any dividends.

Crawford, who had his worst season as a major leaguer during his first year in Boston in 2011, has yet to play a game in 2012 because of wrist and elbow injuries. He had his wrist surgically repaired in January. While he was rehabbing during spring training, he suffered an elbow strain. Crawford only recently began hitting and throwing and hopes to return to the lineup later this summer. Meanwhile, his seven-year, $142 million deal looks worse and worse every day.

Year 3 of Lackey's five-year, $82.5 million deal will be a complete washout as the right-hander recovers after offseason Tommy John surgery. There is one silver lining, however. Epstein included in his deal a clause that added a sixth-year team option at the major league minimum should Lackey go under the knife for an elbow injury at any point in the deal.

At the time of the Lackey signing, the Red Sox baseball operations department discussed "preserving" and "maintaining" as much starting pitching as possible. Management knew the pitchers it developed, including Jon Lester and Clay Buchholz, would complement veterans such as Josh Beckett, Curt Schilling and Daisuke Matsuzaka.

"We were trying to horde as much good starting pitching as possible, because we felt like that was part of what would allow us to remain good in the American League East, to protect the starting rotation. That winter, Lackey was the best starting pitcher on the market," Cherington said Thursday in an interview with Boston sports radio station WEEI.

It's quite obvious that the only people Lackey wants to play for and impress are his teammates. He despises the media and would like to be left alone. As he said in a brief discussion during spring training, he plans on coming back stronger and wants to win a World Series in Boston so he can shut everyone up.

"He's pitched hurt," Cherington said. "That's the reality for the better part of his time in Boston. ... He's pitched through a lot of pain and gutted it up, specifically last year. But it's gotten in the way of him being what he had been in the past. I remain stubborn in my belief that John Lackey will be a very good pitcher for us again once he's healthy."

Epstein's mistakes did not end with the starting rotation.

Every offseason during his tenure, Epstein would reiterate that there was too much risk and not enough reward in signing a relief pitchers to big-money contracts. Instead, he would mix and match the arms in the bullpen, to varying degrees of success. Then, prior to the 2011 season, Epstein gave right-handed reliever Bobby Jenks a two-year deal worth $12 million.

Due to a slew of injuries, Jenks has pitched only a total of 19 games since coming to Boston. He had back surgery last winter and when he arrived in Fort Myers, Fla., for spring training, acknowledged that he had suffered life-threatening complications from that procedure. His health and career status are unclear at this point. The Sox reportedly are seeking a settlement that would end his tenure with the team.

Cherington was Epstein's hand-picked successor, and he even sounds like him in both tonality and vocabulary. So how do we know Cherington won't fall victim to the same pressures that pushed Epstein into decisions he'd later regret?

We don't. But at least the current GM recognizes the give-and-take struggle between the baseball operations and business side of the team.

"The success of the team on the field is the gasoline that runs the engine of the business," Cherington said. "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."

Fans and players have been spoiled by the fact that the Red Sox won the World Series in 2004 and again in 2007. After failing to reach the postseason the past two years, and a lot of money seemingly wasted at this point, Cherington is trying to right the wrongs.

"Building winning teams is the best recipe for the baseball business in Boston, and it's our job in baseball operations to go and execute that," Cherington said. "Every decision has a short, medium and long-term impact, and it's our job to balance all of those things."