Like new Red Sox first base coach and former Phillies GM Ruben Amaro Jr., former Red Sox GM Ben Cherington is not jumping back into another front office job. Unlike Amaro, Cherington’s alternate path comes as something less than a shock.
Cherington has been hired by Columbia University as an executive-in-residence for the spring semester. He will teach a class on leadership in the university’s graduate sports management program.
The idea of Cherington joining a faculty is a relatively natural outgrowth given how he approached his own career path. Most notably, in 2009, Cherington enrolled in a full-time, four-week course (two weeks in October, during the postseason, and two weeks in January, during arbitration filings) on leadership in the Harvard Business School’s Executive Education program.
The program offered Cherington, at a time when he was trying to ascend the final rung of the ladder to a GM role to which he’d aspired for years, a chance to challenge himself both within and outside of the game.
“A big part of developing as a leader is being comfortable with being uncomfortable, and exposing yourself in ways that maybe you’re not used to. … The [Harvard Business School] program itself is not designed for a baseball ops staffer, but it intrigued me in different ways,” Cherington once explained. “They’re not talking about the scouting process, negotiating major league contracts or any of that stuff. It’s a much different curriculum. But aside from the specificity of the curriculum, it appealed to me as something I could do perhaps to challenge myself.
“I had probably been uber-focused on baseball even before college but certainly from a professional standpoint since I was in college. During college that’s all I thought about doing, was working in a front office. I played baseball in college, didn’t go abroad because I didn’t want to miss a practice,” he added. “I don’t regret a thing from college other than maybe I didn’t spend time overseas. This was sort of an opportunity to see something different.
“I learned something about myself, about best practices and leadership, but a big part of it was just being exposed to the world. The world kind of came to Cambridge. I was in a workroom with an oil executive from Saudi Arabia and people I wouldn’t have had contact with were it not for the program. At the time, it was really good for me.”
Cherington’s interest in examining best practices in decision-making and business, his curiosity about challenging himself in different environments, intersected at times with his belief that there is a world in which he has a chance to make an impact (in this case, teaching) outside of the game – something he admitted to considering from time to time while in the job.
“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,” Cherington said in 2014. “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.”
At that time, of course, Cherington wasn’t contemplating a next career move. Indeed, he was nearing a multi-year contract extension. That said, once Cherington made the decision to leave the Sox after the team decided to hire Dave Dombrowski as the president of baseball operations, the chance to use the academic world as an opportunity to recalibrate should seem anything but surprising.