Ben Cherington pushing Sox to peak

BOSTON -- Boston Red Sox general manager Ben Cherington has become the modern-day version of Sisyphus.

In Greek mythology, Sisyphus was a punished king who was forced to push a boulder up a hill, only to watch it roll back again, and again and again.

After former Red Sox GM Theo Epstein decided to jump ship to become the president of the Chicago Cubs this past October, Cherington was left with a major mess. He needed to find a manager and a pitching coach, as well as tweak the roster in hopes of helping the Sox reach the postseason for the first time since 2009.

Despite how poorly the Red Sox have played on the field -- not to mention the season-long drama off the field -- Cherington believes this organization will get back to the top.

"When things aren't going well, it's not as fun as when things are going well," Cherington said. "But I don't feel any different than the day I took the job. I know the task. I know what [the] task is and what we need to do. I believe very strongly in the future of this organization and I believe in the outlook.

"We've got a lot of good things in place here. We have a good core of players. We have a strong farm system. We've got a lot of good people. The performance at the major league level is always going to be the focus, as it should be, and that needs to improve."

In the midst of an uneven season hovering near the .500 mark, fans and media members alike have been calling for first-year manager Bobby Valentine to be fired. But Cherington stood up and spoke publicly Monday afternoon, saying Valentine will be the manager for the foreseeable future this season.

As with any relationship, it hasn't been perfect between the players and Valentine, but Cherington hasn't turned a deaf ear to either side. He's worked tirelessly -- he even has some gray hairs to prove it -- to find relative peace and harmony that will translate into wins on the field.

For all the talk of "rats" and "snitches" in the clubhouse complaining directly to upper management and ownership, Cherington said that's simply not a realistic issue.

"I've talked to players plenty this year," Cherington said. "It's no different than any other year. I think, occasionally, it's appropriate for ownership to talk to the players. They have a lot at stake here and they should do that. I don't see it as different [from] any other year, and no players are running up the back stairs.

"I've had conversations with players in the open light of the clubhouse, I've had conversations on the phone, just like any other year. The content of those conversations will be private, but I will tell you that they've been constructive. They've been focused on what's been going on out here and trying to get this better."

Unlike most GMs in the big leagues, Cherington has a unique relationship with many of the current Red Sox players. Like many of them, he grew and developed in the organization; he was a scout, baseball operations assistant, coordinator of international scouting, assistant director of player development, director of player development, vice president of player personnel and assistant general manager before he was named to his current post.

He's built strong relationships with all the homegrown talent, including Dustin Pedroia, Clay Buchholz, Jacoby Ellsbury and Jon Lester.

"He's a good guy," Pedroia said of Cherington. "He gets it."

Those relationships, now more than ever, are crucial to this team's success.

"I think it's an opportunity because the relationships that were established with players previously allows me to be honest with them and to be candid with them," Cherington said. "Sometimes that's, 'Hey, guys, we all need to look at ourselves first. If there's a concern with what's going on, let's look at ourselves first.' Hopefully the relationship that exists allows me to have that conversation.

"Whenever there's frustration expressed, wherever it's coming from, you've got to go to the person that is the source of your frustration. I have to do that, players have to do that, Bobby has to do that, coaches have to do that, and that's happened."

Lester has struggled this season. For the first time in his career, he hasn't been the dominant, left-handed ace he's expected to be. After the All-Star break, when the team was in Tampa, Lester and Cherington had a conversation about everything other than baseball and pitching.

"That's nice to have, especially with your GM," Lester said. "I know he's being pulled in a million different directions, and his mind is going a million different ways, and for him to take 10 or 15 minutes to B.S. with me, I think that helps. It's a good thing for us to have that type of built-in deal where we can just talk.

"I wouldn't call it unique; I would say it's familiar. With Theo, you had to learn him and how he communicated and how he handled different things. Really, the only time I ever dealt with Theo was just during my contract because I never had any problems or any issues that I had to talk to him. This year, with Ben, it's been a little different just because of some personal stuff, and with my pitching, I feel like I've dealt with Ben a little more. It's that familiar relationship. He feels comfortable coming to me and not being a GM, and we can just talk. I think he's done a good [job] of being both present and able to communicate. I think he's done a good job, so far."

From the time Lester became a pitching prospect in the Red Sox organization, he has not seen a change in the way Cherington deals with the players or handles certain situations.

"I don't feel like he has," Lester said. "I'm sure it's pretty stressful for him, but it doesn't seem like it's gotten to him, which is good. Hopefully, he can continue that. This is a tough place to be anything, and to be a GM, a first-time GM in this organization, I'm sure it hasn't been easy for him. With those little bits he does of grabbing individuals and just talking to them, I think that eases a lot of, I wouldn't say tension, but he is the GM and you have that boss-type of relationship with him, and when he's able to do something like that, it eases any problems because you feel comfortable addressing it with him.

"The on-field stuff, you deal with your manager, but when there are other things that need to be addressed, whatever it may be, to be able to feel comfortable enough to go up to him and say, 'I don't agree with this' and he'll listen to you and not tell you to get the hell out of the room. That's a plus and that obviously makes working conditions a lot easier. He's done a good job."

Buchholz agrees that Cherington has remained consistent.

"Every time I see him, he says hi and we'll talk a little bit. It's not like a friendship because that's one of the things you have to keep away from each other. Part of the job, if a player is getting traded or getting released, it would be pretty hard for two friends to be saying that to each other. He keeps it good in that aspect of it and he's an easy guy to talk to."

Buchholz added, "He probably has a better relationship with the 2004 and 2005 group that was in the minor leagues when he was the coordinator. He's always been a guy you could talk to. He's always been good. He's always told me the truth and never beats around the bush, and that's what every guy in here would ask for.

"He's organized, he knows the game and he's able to talk to players if they were going through some issues, and everybody has their issues. In that aspect of the job, I don't think there's a better person for it."

Red Sox catcher Kelly Shoppach was one of the top prospects in the organization before he was sent to the Cleveland Indians in 2006 as part of a six-player trade in which Boston acquired outfielder Coco Crisp. Shoppach knew Cherington well in those early days, so when the Red Sox wanted to sign a veteran receiver for one season until current prospect Ryan Lavarnway was ready for the big leagues, it helped Cherington sign Shoppach as a free agent.

"He's pretty much the same as he was," Shoppach said. "Now, at this level, it's been weird but it's cool. To have a previous relationship with a guy, and I'm sure he knew, without a big interview process, what kind of guy he was getting in me during this offseason. I'm sure he felt some comfort in knowing what he was going to get. You build a lot of relationships with a lot of people over the years, and you try not to burn any of them because you never know when you're going to need them again."

When Shoppach was originally with the Red Sox, Cherington was director of player development. Now, he's the boss.

"He's obviously in a tough spot because it's a different job," Shoppach said. "Even though it's the same players, some GMs treat it differently than others. Our GM in Cleveland [Mark Shapiro] was kind of behind the scenes, and we saw him occasionally. He's a good guy, and would stop and have a conversation with you. In Tampa, [Andrew] Friedman's in the clubhouse every day virtually hanging out, so everybody has their own style and I know that Ben is trying to build one at this level because it's the first time he's been in the public eye. Anytime you have a job for the first time, whether you know the players or not, there's a learning curve for everyone."

Carl Crawford signed with the Sox last season, and found that both Epstein and Cherington were always accessible to the players.

"Theo was open, too," Crawford said. "They're both pretty much the same. They're easy to approach if you need to talk to them about something. It's not hard to get that conversation going. Communication is always good. If there's an issue that comes up and you need to talk to him about it, it's good to have that open line of communication."

In an email response to ESPNBoston.com, Red Sox owner John W. Henry said he "agreed" with the players' comments that Cherington has been "impressive" in his first year as GM. "But it's been a long day, so let's leave it at that for tonight," Henry wrote.

No matter how this season ends, Cherington, who graduated from Amherst College with a degree in English, hopes his story will ultimately diverge from a seemingly Sisyphean fate. It's up to his Red Sox to once again reach the pinnacle without everything falling back downhill -- again.