NEW YORK — There was no rush to the next thing.
Ben Cherington had spent his entire adult life working for the Boston Red Sox. When he parted ways with them last August, electing to leave his post as general manager after the hiring of Dave Dombrowski as president of baseball operations, he felt a need to process both his 18-year history as an employee of the Red Sox and the abrupt end of that tenure.
Undoubtedly, there could have been opportunities to race forward. Cherington’s relationships throughout the game are such that a number of teams would have welcomed him to their front offices. But Cherington wasn’t interested in racing into something so close to what he’d just left behind, particularly given the difficulty of his last two seasons with the Red Sox.
Last year, after the amateur draft in June, Cherington worked with team ownership to examine what led the Red Sox into two straight disappointing seasons, an examination that included Cherington’s own role in the matter. When he left the Sox, he recognized that his investigation remained incomplete.
“Although I think I learned something from that exercise, when you’re still in the middle of the fire and the trees are kind of burning around you, it’s hard to see where the fire started,” said Cherington. “Although I didn’t leave under the circumstances I wanted to, I did have the benefit of some distance to look at it again.
“I was pretty quickly well past the acceptance part of it. Are there things you’d do different? Sure. Were there mistakes made? Sure. Did it lead in some way to short-term results not being there? Sure.
“And so once you sort of get past that, I think it’s sort of easier to just keep looking at it. Then it’s just about trying to learn from it, sort of past the point of whether, ‘Wait, did I have anything to do with this?’ ”
Any hesitation about answering in the affirmative was erased by what happened after his departure. The Red Sox had long cultivated a belief that one of the fundamental responsibilities of their organizational leaders was, in Cherington’s words, “to find your replacement.”
So there was some satisfaction when Dombrowski promoted Cherington’s assistant GM, Mike Hazen, to the GM role, and likewise a feeling of pride when Dombrowski retained nearly every other member of Cherington’s front office. Yet there was also a corresponding conclusion.
“In some ways, that made it hard, too — because there’s sort of one change, and that was it,” Cherington said with a chuckle.
Cherington felt he could re-examine his career in a productive way so long as he wasn’t immersed in the day-to-day operations of a team. Because he was no longer working for the Red Sox, he could hold a wide variety of conversations that had been impossible in his former job. He could engage other baseball executives in a way that would have been almost impossible with a competitor. He also had the time to reach out to people in other walks of life.
Among the people he contacted was Vince Gennaro, president of the Society for American Baseball Research and the director of the sports management program at Columbia University’s School of Professional Studies.
“I was No. 63 on the list,” Gennaro joked of Cherington’s conversations.
Gennaro and Cherington had met briefly on a couple of occasions, but didn’t know each other particularly well. Still, Gennaro found it hard to contain his enthusiasm about the prospect of involving a former major league GM, just 2½ years removed from a championship, in his program.
“As a potential guest lecturer . . . Ben would have been an unbelievable get,” said Gennaro. “I immediately started thinking, ‘Wow — if Ben was willing to become involved in some way with the program . . .’ ”
‘It sort of fit’
Over lunch, Gennaro proposed that Cherington join the program as a guest faculty member for the spring term. Within a couple of days, he agreed.
The idea of teaching resonated, particularly as the conversation quickly focused on the idea of Cherington teaching one of three sections of the class on “Leadership and Personnel Management.”
Cherington had gone to graduate school for sports management at the University of Massachusetts. In 2009, while working in the Red Sox front office, he’d taken part in a Harvard Business School Executive Education course on leadership.
Whereas the idea of a front-office job at this stage wasn’t appealing, the class represented a sort of vehicle, said Cherington, “to just really understand more about what had happened and what my role in it was.”
Moreover, the opportunity to work with students would hearken back to some of Cherington’s favorite experiences with the Sox, chiefly working with other members of the organization on solving problems.
“It sort of fit where I was in my life with everything,” said Cherington.
The roughly three-month class would visit individual topics each week, using readings (some on sports, but also from other areas such as the Civil War), case studies, academic research, guest speakers, and Cherington’s own experiences to illuminate a subject. Former Sox pitcher Craig Breslow, for instance, joined a class on “Leadership Models: Identifying Mission and Building Culture.”
Another lecture was titled “High-Functioning vs. Dysfunctional Teams and Team Chemistry.” The description in the course syllabus: “Professor Cherington will discuss . . . highly functional and dysfunctional units, with consideration of all factors that impact a favorable work environment.”
While Cherington said he’s been careful not to betray confidential information, he’s been open to examining some of his own choices as Red Sox GM — both good and bad — in conversations with his students.
“I don’t mind talking about my own shortcomings, my mistakes,” said Cherington. “I think there is plenty we did right over time. I don’t mind talking about the things that we didn’t or that I didn’t — even things I would do differently. In that sense, I’m fine being in the dunk tank.”
That said, the perch has been relatively comfortable. More than half of Cherington’s students are from abroad, and the group is more interested in questions about managing executive-ownership relationships and balancing short- and long-term interests than about the decision to sign Hanley Ramirez.
But there have been topics that would offer considerable fascination — the Sox’ inability to fulfill their dual ambition to “win today, preserve tomorrow”; the nature of managing relationships within organizations; and the difficulty of remaining true to one’s leadership principles given the competitive demands and context involved in the job.
The topics seemingly have sharpened Cherington’s views of what happened during his time in Boston. Even as the organization’s emerging young core — which Cherington proved resolute in preserving — appears to have the team back on a promising track, he understands why he is no longer GM of the Red Sox.
“Results do matter,” he said. “In Boston, you know they matter. That’s fundamentally a part of the job.
“Yes, there were reasons why we did everything we did, but the bottom line is we didn’t perform well enough for two years. When that happens in a place like Boston, there’s a lot of pressure on the institution to make change, because it’s a business.
“That change happened. If I’m going to learn something from it, I think I have to embrace that the results weren’t there, and why was that.”
To Gennaro, Cherington’s involvement has meant a great deal, starting with the publicity it generated.
“ ‘Applications above replacement,’ I don’t know what Ben’s value is there,” said Gennaro. “I wouldn’t be surprised [if his presence increased applications]. I get it referenced in some applications.
“Columbia has an iconic brand, but when you can marry that with the announcement that we were able in our program to attract Ben Cherington, it means a lot. We had letters from high school kids around the country who wanted to know if they could audit the class.
“It made more people aware of our program than might have been.”
Gennaro has invited Cherington to continue with the program in the fall. Cherington is not ready to say whether he’ll accept.
What lies ahead?
The semester is nearing its end, and with it will come the question of what comes next.
“I need to figure out what the rest of life looks like,” said Cherington, who now resides outside of New York. “I’ve really enjoyed it, so in theory, I’d like to do it again. Whether I can or not, whether it fits, I don’t know yet.
“I haven’t ruled anything in or out, other than I’m going to work again. I’m 41, I’m sort of, roughly, I don’t know, halfway through working life or something like that — most people would say that. So I know I’m going to work. Really, that’s what I’m thinking about. What do I want to do, what do I enjoy doing, who do I want to do it with?
“I think doing it in baseball is definitely still something I think about a lot. That’s as far as I’ve gone with it. Teaching I’ve enjoyed a lot. Should I continue to teach? Maybe, if it fits in the life.”
He is watching — truly watching — more baseball now than he did before he was GM, and it’s clear that he continues to devote plenty of thought to the game. He seems at peace with his Red Sox past.
“I’m definitely glad I did it,” said Cherington. “I don’t know that I can answer in a simple way what the job was like, but I’m definitely glad I did it.
“I had a couple conversations with people this fall who were entering into their first GM experience. One of them asked me, ‘So are you glad you did it?’ I said, ‘Absolutely, because even when it doesn’t go well, even when you have really tough moments and it didn’t end the way you wanted it to, it’s still an incredible experience.’ ”
Given the difficulty of what he experienced at the end, it seems fair to wonder: Would Cherington want to be a general manager again?
“There probably was a time in my career where I was aspiring to a title because at a certain point in your career, and if you have aspirations to be a GM, which I did, there are steps you have to do to get there,” he said. “There are titles that are of importance to some degree as you’re sort of building yourself to be prepared to be a GM and then be a GM. I was aspiring to that. I don’t feel that anymore.
“It dawned on me at the end of class. I asked everyone to come up with an example of someone they consider a leader in their life. There were a lot of parents, a lot of teachers, coaches, bosses, what you would expect.
“Nobody said themselves. That’s something that we’ve spent time on. Don’t wait for it to happen around you, don’t wait for the leadership to happen, don’t wait for this stuff to happen. You have to do it yourself.”
It’s an aspiration that will help guide Cherington’s future, as he pursues something both meaningful and enjoyable — in a place where he can remain true to the leadership principles that he values.
For now, he seems to have discovered both in a classroom setting that is far removed from the thrilling and sometimes overwhelming chaos of 4 Yawkey Way.