Ben Cherington spent years aspiring to be a major league general manager, working from obscurity as a ramen-eating intern in the Cleveland Indians front office to the bottom rung of the Red Sox organization and then slowly moving up. His goals were clear, and his curiosity in that pursuit was uncommon.
In 2009, his front office career was at something of a crossroads. He'd been with the Red Sox — the organization for which he rooted all his life — for more than a decade, and at a time when he'd risen as high as he could inside the front office (to assistant GM, with Theo Epstein in place for what seemed likely to be years), he wondered how he could avoid the trap of having his ideas becoming stale. He wanted a challenge.
So Cherington enrolled in a Harvard Business School Executive Education course on leadership, a rigorous on-campus program that required him to part with the team for two weeks in October (at a time when the Sox were getting swept by the Angels in the Division Series) and for two more in January (when he had to duck out of class, at one point, to take a call to settle an arbitration case).
The program shaped his views of leadership, in many ways giving greater definition to implicit beliefs he'd already held. Foremost, beyond the opportunity to have an experience with international executives that in many ways alleviated his regrets about not getting to study abroad while in college at Amherst, Cherington identified three critical aspects of leadership to which he aspired:
■ unflinchingly high standards, as demonstrated by the thoroughness of the course design;
■ authenticity that permitted those in a position to interact with him to know that there was no artifice in his personal conduct;
■ and accountability not just for his own actions but for those of any group that he represented, particularly in times of adversity.
Focus on improvement
Two years after taking that course, when Epstein left to become president of baseball operations for the Chicago Cubs, Cherington had the opportunity to assume the job he'd long awaited. And within months of becoming Red Sox GM, he was enmeshed in a state of crisis.
Cherington reminded himself during a hard 2012 season — the first unexpected descent into last place over which he would preside, and for which he would assume public responsibility at every turn — that numerous components of a road forward existed for the Red Sox. That was what he focused on.
He did not permit himself to wonder about his job security. It simply wasn't relevant.
"I've known for a long time that no matter what title I have or would have that there's going to be a time in life that that's over, after baseball is over or after a particular job is over," Cherington said in early 2014. "Being good matters to me. Being good at my job matters to me a lot. But I've never felt like the title defines who I am.
"We're just trying to be good, trying to be better, so I was just focused [in 2012] on doing whatever I could to help try to make the situation better. Whatever happened for me personally didn't matter. It just wasn't a thought in my mind at all.
"I just saw it as an opportunity — an opportunity to try to help make a situation better. And there were a lot of people I trusted who were trying to do it with me. I didn't feel anything about my job.
"It doesn't mean that it wasn't a fair question [whether he was in danger of being fired]. Look, this is a performance, bottom-line business. If you don't get performance, at some point, especially in a place like Boston, there's going to be change. We know that. But I never worried about that aspect of it."
Cherington acknowledged the finite nature of his position, the fact that it had an unknown expiration date that would arrive by unknown terms.
"There's no doubt that there are moments in this job that are a long way from what you envision when you set out to work in baseball," said Cherington. "There are thoughts you have about what working in baseball would be like with a sort of ultimate goal of being a GM. There are moments that are very far from what you imagined it and what you hoped it would be.
"When that starts to impact your ability to be who you are, to lead, to be the person who you want to be from day to day, you have to think about that. The question becomes, OK, I have an obligation, as long as I'm in this job, to provide something of value to the organization, to ownership, to the people who are employing me to do this and asking me to do this. If for any reason I can't do that, then I can't do that and I shouldn't be doing it.
"A big form of success, in my opinion, is being able to have a say or a voice in when that time is. Many people don't have that opportunity. And I'm not suggesting I will.
"But I've certainly thought about the amount of time that I can be a contributor in this job. I think that's different for everyone. It was different for Theo and it will be different for someone else.
"It's a personal thing. We all react differently. We all have different interests outside the game. We all have different visions for how our life is going to go, the different things we want to do. So it's not a current topic, but what's most important to me is it's important to me to be good at what I do.
"It's important to me to make a contribution, absolutely. It's equally as important to be part of something special for the Red Sox, the organization I've been with for 16 years now and the organization I've rooted for since I was 3, to be strong. Really strong.
"And that, in the long run, will have very little to do with me. It will have a lot to do with a lot of other people who are here past my time here. Whatever time I have in this job, I want to do whatever I can to help make sure that those things are happening — that the organization is strong and this can be a special place.
"If I ever feel like I'm not helping that, then I'm not helping it and I shouldn't do it."
Defining his tenure
That view of leadership almost surely informs a great deal of Cherington's current position.
In recent weeks, he revealed little discomfort at the idea that the Red Sox might explore the possibility of hiring a president of baseball operations above him; if it was in the team's best interests, they should do it.
He accepted and welcomed the opportunity to work with bosses. He had no qualms about hiring a former GM, Jerry Dipoto, as a consultant to evaluate the organization's players and decision-making — it was, in fact, a decision driven according to one team source "100 percent" by Cherington in a quest for improvement.
But Cherington declined to work as GM under Dave Dombrowski, at a time when he was invited to remain at least for the final year of his contract in 2016 (with the team holding options on his services after that). Given the lack of philosophical alignment (the use of analytics, prospect/player valuation) between the Sox under Cherington and the Tigers under Dombrowski, even for two executives who viewed each other with mutual respect, it made little sense to introduce a form of ideological tension that might be detrimental to the club.
The willingness to make himself available to assist Dombrowski with the transition process? Easy, given Cherington's commitment to leaving the Red Sox in the strongest possible position.
Cherington's tenure as Red Sox GM will be defined in the most straightforward of terms. He served as the head architect of a championship team in 2013 whose meaning to a battered region is hard to overstate. He oversaw two (and, by the end of 2015, almost surely three) last-place finishes. Those are the clearest ways of judging his work.
Beyond that, he presided over the refilling of a pipeline of talent to the big leagues that had run dry, leaving some foundation pieces — Xander Bogaerts, Mookie Betts, Eduardo Rodriguez, Blake Swihart, Henry Owens, Yoan Moncada, Rafael Devers, and others — who might be able to help establish the sustainable success that has been elusive.
Yet the fierce loyalty of those who have been working alongside him and the considerable respect for him from those around the game will have less to do with those measures than they do with the accountability, authenticity, and aspirations to excellence that characterized his leadership of the Sox.
Those traits — along with the World Series trophy, the last-place finishes, and whatever may come of the players he leaves behind for Dombrowski — defined his time as Red Sox GM. The title did not.
Video: Dave Dombrowski is ready for the challenge of leading the Red Sox
(Boston Globe) Dave Dombrowski is ready for the challenge of leading the Red Sox. (By Alan Miller, Globe Staff)
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