It was a time when general managers had suddenly been turned into the iconic faces of franchises.
The Red Sox had engaged in a public and dramatic courtship of Billy Beane, the GM who was quickly coming to be portrayed as the single most important individual in the success of the small-market Oakland Athletics. The Sox flew him across the country on a private jet and toasted his agreement to become the GM who would end Boston’s 86-year championship drought, only to see Beane change course and elect to stay with the A’s.
That, in turn, opened the door for the Sox to promote 28-year-old Theo Epstein to the head of their baseball operations, making him the youngest person ever to occupy the post. In addition to his youth, Epstein brimmed with intellectual energy and passion for the game while displaying an atypical hipness for his job.
He became the guitar-playing GM who immediately served as the face of the new way of business on Yawkey Way. Beyond that, he gave the team’s blueprint its slogan, the crisply articulated notion of a “scouting and player development machine” immediately burning into the consciousness of New England.
Less than two weeks later, and with no real fanfare, Epstein unveiled his new front office structure, which included outside-the-organization hires such as Assistant GM Josh Byrnes and a pair of key evaluators in Bill Lajoie and Craig Shipley, both of whom were named special assistant to the GM. And then, there was one internal promotion.
Ben Cherington was elevated from assistant director of player development, the role he’d served during the 2002 season, to director of player development. It was the type of move that often gets lost in transaction listings, but internally, Cherington was being elevated formally to a pivotal role. After all, the idea of the scouting and player development machine would rest heavily on the man in charge of the team’s farm system, and who would eventually ascend to the title of Vice President of Player Personnel, with jurisdiction over both player development and amateur scouting.
Epstein had given the Sox their motto. But in many respects, Cherington was the man who was being asked to construct the so-called machine, meticulously developing the blueprint (and, literally, a manual) to turn a farm system that had yielded few impact major leaguers into a factory of young, inexpensive, dynamic talent.
When the reconfigured Red Sox front office got together to assess the state of the organization behind closed doors, sound bites gave way to substance, as the Sox committed to developing every minor leaguer in their system to his fullest potential. And inside the organization, Cherington -- who had spent most of 2002 working with Epstein, then an Assistant GM, to evaluate the entirely of the Sox system -- immediately became a critical voice, someone whose patience and methodical, comprehensive approach to problem-solving made him an ideal person to rebuild the farm system.
“That first [organizational] meeting, he spent a lot of time talking about the whole system, about our minor league talent. Ben’s knowledge of those players had him effectively leading the meeting,” Byrnes, now Padres Vice President of Baseball Operations, recently recalled. “It was his passion. I think it was his determination to make the Red Sox the type of organization that could develop impact homegrown players. He was a key part of that process.
“Theo and Ben set a tone that this was what we want to be. We talked about 100 players with 100 people in room. Those were long days. If nothing else, it set a tone that this was our organization, these are our players, and let’s build from within.”
Cherington has operated hand-in-hand with Epstein in the construction of the Sox organization during the latter’s tenure as GM. And so, at a time when it appears likely that Epstein will leave the Sox for the Cubs, and at which the Red Sox owners believe that their organization’s baseball operations model remains highly successful, Cherington represents the obvious successor to Epstein.
Cherington can provide an air of continuity and stability at a time when the organization is amidst potentially significant changes, a task with which he is familiar. It was, after all, Cherington who was appointed -- along with Jed Hoyer -- as co-GM of the Red Sox in 2005, when the Sox were keeping the seat warm for Epstein to return as head of baseball operations.
Cherington and Epstein harbor similar baseball philosophies, and Cherington often raves about the organizational culture created by Epstein, whom he describes as a mentor. Yet while the two are roughly the same age (both are 37) and share many beliefs, they also possess very different personalities and very different backgrounds.
TWENTY-TWO GOING ON THIRTY-FIVE
Amherst coach Bill Thurston recruited Cherington as a pitcher out of Lebanon High School in New Hampshire. While his stuff (highlighted by a mid-80s fastball) did not stand out, he had both control and an advanced knowledge of the game, and he was, in Thurston’s terms, “a baseball rat” who was determined to maximize his abilities.
As a freshman, Cherington was Amherst’s No. 5 pitcher. By his sophomore year, he was the No. 3 pitcher on the squad, though in stature, he was something more than that.
“The players had so much respect for Ben as a person and a player and his work ethic, even though he was a No. 3 pitcher, he was the leader on the pitching staff,” said Thurston. “He was a leader not because he said a lot, but because of his actions.”
Yet Cherington’s baseball career would take a dramatic -- though perhaps inevitable -- turn after that season. The winter of his junior year, he started playing hockey. While working out with the hockey team, he suffered a shoulder injury that turned out to be an undiagnosed torn labrum.
When he went to spring baseball practice, Thurston saw immediately a changed arm angle that suggested an injury. Initially, Cherington held out hope that it was just a strain before an accurate diagnosis revealed the need for surgery. The pitcher would miss the rest of his junior year, and his attempt to return as a senior likewise proved unsuccessful.
As a player, his career was done. Yet the injury commenced Cherington on his professional path in baseball.
“He wasn’t a paid coach,” said Thurston, “but he wanted to be around the team.”
Cherington served informally as a coach, working with the pitchers for his senior year. Then, after graduating from Amherst, he got a Master’s from the UMass Sports Management Program while serving as the pitching coach at his alma mater for a year. It was then that Thurston became convinced that Cherington had a future in a big league front office.
The former pitcher asked uncommonly astute questions, showed strong skills as an evaluator of talent and his interest in learning about the game and competence both stood out. His maturity was also striking, a fact that became comically evident on a spring baseball trip through Florida in which Cherington roomed with another assistant coach, Chuck Roys, who was on the Amherst staff after decades as a college head coach.
“After two nights, I was having breakfast with Chuck in the morning,” recalled Thurston. “[Roys] said, ‘How old is Ben, 35?’ That’s his maturity. Ben was 22 years old.”
Thurston reached out to one of his former players, Red Sox GM Dan Duquette, suggesting that he hire Cherington.
“I said this kid’s a serious kid, sincere, really knows the game, someone you can really count on,” said Thurston.
Duquette said that he did not have an opening at the time, but recommended that Thurston contact fellow Amherst alum Neal Huntington, the current Pirates general manager who was then an assistant farm director for the Indians. It was there that Cherington spent a pivotal year in his professional development.
NOURISHED BY BASEBALL (AND FREE MAC & CHEESE)
When Cherington joined the Indians front office in 1998, Cleveland was amidst a run of five straight AL Central titles. That run was fueled by an extraordinary young core of players on the field and a group that could be described in similar terms in the front office.
The 1998 Indians featured seven current or future general managers. In addition to Cherington (assuming one counts his tenure as co-GM of the Sox), GM John Hart had a staff that included Mark Shapiro (now Indians president after a decade as GM), Dan O’Dowd (Rockies GM), Huntington, Byrnes (who went on to become Diamondbacks GM) and Paul DePodesta (former Dodgers GM).
That front office, as much as any, was responsible for changing the landscape of baseball operations. The profile of the traditional “baseball man” who had played and/or scouted before graduating to a front office was being challenged, with the Indians unleashing a wave of liberal arts-educated twentysomethings who were ready to rethink traditional forms of talent evaluation.
Cherington fit right into the mold. He was named video advance scout -- a role previously held by Byrnes and DePodesta -- in which he was solely responsible for breakdown of the opposing teams whom the Indians were preparing to face.
The hours were long, the work all-consuming but immensely rewarding.
“I still go back to that time as a pretty important and fundamental experience for me in my career. … In some ways it was the Moneyball theory looked at through a different lens,” Cherington recalled this spring (in this podcast). “It was finding undervalued assets, finding people who could make an impact on the team through good decisions, and finding them when they were young, finding them when they would work incredibly cheap, when they would work incredibly long hours, and putting them in an environment where they could learn enough about the game and where they would interact with the staff and scouts to eventually be in decision-making positions and impact the team.
“The year that I was there, a 100-hour week was a light week,” he added. “[The hourly pay] was embarrassing. I lucked out, because at the time, I had a friend from college who’d gotten a job from Nestle, which was based in Solon, Ohio, just outside of Cleveland.
“They used to own Stouffer’s and a bunch of other food brands. And he would give me supermarket coupons where you could literally go into the supermarket, and it wasn’t a discount, it was free. You could grab a Stouffer’s mac and cheese and it was free. So I would go to the supermarket once a week, haul out 50 boxes of Stouffer’s frozen foods, and that’s what I lived on for the summer. That, and I paid rent, and that was my life.”
Just as Byrnes and DePodesta had done before him, Cherington made a strong impression with his work. Though he was a one-man department in his video advance role, he connected to other parts of the Indians front office, producing strong work at the same time that he tried to absorb the rich opportunity that existed in the Cleveland front office.
“To see Ben interact first hand with a major league staff member, with a player, the general manager, the assistant farm director, the baseball operations assistant, in that role, he showed us very quickly that he had a good feel for what played, why it played and how it played at the major league level in his role as an advance scout,” said Huntington. “He showed an advance baseball feel at a young age, as well as a maturity and an intelligence beyond his years.
“Ben had the ability to impact an organization on both fronts, the subjective front and the objective front. Obviously the intelligence to understand, maybe not perform advance metrics, but to understand advance metrics. And then, having the baseball background -- despite not having played professionally -- to understand evaluation, development and projection. That’s what led him to a variety of roles in Boston.”
BACK TO BOSTON
Duquette had not forgotten about Thurston’s glowing recommendation of Cherington. Only one other time had his former coach -- a widely respected evaluator in his own right who worked as a consultant to Dr. James Andrews at the American Sports Medicine Institute in Birmingham, Ala. -- spoken so highly of a player, and that was when Thurston convinced Duquette to hire Huntington in Montreal. Within six months of that hire, Duquette had called Thurston and pronounced Huntington to be a future GM.
And so, after the 1998 season, Duquette saw an opportunity to bring Cherington to the Sox, hiring him initially as a Mid-Atlantic area scout. Almost immediately, Duquette saw someone with the potential to one day assume his own job.
“When people come into a work situation and have talent, it’s obvious. That’s a guy that had talent,” said Duquette. “It was obvious to me that if he applied himself, he could be a general manager.”
For that reason, Duquette wanted to expose Cherington to as many different aspects of baseball operations as possible. He served initially as an amateur scout, was brought into the front office and then spent two years as the coordinator of international scouting.
It was a far-reaching cross-section of experiences that reflected the potential that was evident in Cherington even in his early-20s.
“He’s a bright guy, and he has a lot of passion for baseball. My idea was to get him as much exposure as I could to all aspects of baseball operations so he could learn the business from the ground up,” said Duquette. “I knew that in order for him to build a foundation, he needed exposure to amateur scouting, professional scouting and player development, so I tried to get him into a position where he could benefit from the experiences he had from the best people in our operation.”
A SUCCESSOR, BUT NOT A CLONE
Once the current Sox owners came on board in early 2002, many members of the Duquette front office were purged. Cherington -- who, along with Director of Minor League Operations Raquel Ferreira is one of just two remaining Duquette-hired front-office employees on the Sox -- was not among them.
Instead, Cherington was named the assistant director of player development in May 2002 before a promotion to head of player development with Epstein’s ascent to GM. He shared Epstein’s beliefs that the foundation of long-term success were to be found in a fertile player development system.
In philosophy and demeanor, he was the right person to work with Epstein to author the 300-page manual that outlined the principles that would guide instruction at every level of the minor league system. By 2005, when the Sox had a Double-A Portland team that featured a star-studded class that included Jonathan Papelbon, Jon Lester, Dustin Pedroia, Hanley Ramirez and several other future big leaguers, the fruits of that effort started to become apparent.
After his stint as co-GM in 2005, Cherington assumed the title of Vice President of Player Personnel, in which he was in charge of the team’s Player Development and Amateur Scouting. He later moved into the role of Assistant GM in 2009, shifting his focus to major league personnel and contract negotiations.
Cherington’s career path has given first-hand experience of virtually every baseball operations department. His familiarity with the Sox organization is unrivaled. He and Epstein are like-minded on most baseball matters, to the point where some who have worked with both cannot recall subjects of meaningful disagreement between the two.
Even on the matter of organizational culture, Cherington points to the model cultivated by Epstein as an ideal one.
“Yes, there’s a reporting structure and technically, people report to someone, and there’s an organization chart and all that, but it’s a very flat environment in terms of the kind of back-and-forth that exists,” Cherington said in the spring. “In Theo’s office, I might be in there one minute, then an assistant the next, then an intern the next.
“That’s actually pretty rare not only in baseball but also probably in most businesses. That really speeds up the development for someone who’s in that position. They get to engage with, I’m biased, but the best GM in the game. That’s a pretty unique opportunity. … We’re lucky to have a GM who really supports that and allows for a very cultivating environment to exist in the front office.”
While it is a culture that Epstein has created, Cherington has been a passionate advocate of the flat hierarchy that prevails in the Sox front office. At one point, he circulated James Surowiecki’s “Wisdom of Crowds” among baseball operations staff members, encouraging the idea that the most intelligent decisions are made collectively rather than individually.
Cherington’s approach to decision-making in many ways reflects the conclusions of that book. He seeks broad cross-sections of opinion from people with different perspectives and backgrounds in order to come to the most thorough decision. His tone comes across almost unfailingly as serious and earnest, and he is described nearly universally (from Thurston to current members of the baseball operations department) as a great, patient listener.
That trait, in turn, helps to differentiate the two, whose demeanors, in some ways, represent a tortoise and hare phenomenon.
While Epstein’s office is typically open to everyone in the baseball operations department, from the Assistant GM to interns, he sometimes possesses an edginess that borders on impatience. He has a sharp, sometimes cutting, sense of humor, in contrast to the more sincere Cherington.
Epstein seeks input from most of those with whom he works, but his personality sometimes lends itself to quick decisions and can render him exasperated when conversations drag on. That, in turn, results in colleagues who sometimes feel as if they are on the clock with him.
That’s not necessarily a bad trait -- indeed, it may help to explain why Epstein is considered by many inside and outside the organization to excel while working against deadlines -- but it does represent a distinction between the current Sox GM and his potential successor.
Cherington, in contrast, is meticulous, someone who wants to leave no stone unturned while always trying to find new lenses through which to explore topics to ensure a comprehensive perspective. He is not averse to forsaking expedient outcomes in favor of thorough decision-making processes. Despite a fiercely competitive nature, he rarely reveals a change in his earnest, thoughtful demeanor.
One colleague once referred to Cherington as being like “the Ice Man,” someone who can grind tirelessly through a subject in order to achieve as thorough a conclusion as possible. As with Epstein’s more impatient style, that can be good and bad, empowering colleagues to voice their opinions at the same time that it can leave peers eager for resolution.
And yet, while Epstein and Cherington have personality differences, the two often arrive at similar conclusions, a reflection of their shared values and philosophies. While the process might be different, the end result is often the same, something that has allowed the two to work together closely to shape the Red Sox front office, and something that likely would make the transition from one to the other seamless.
ARRIVING AT AN UNSURPRISING POINT
In some ways, the different trajectories of the current Red Sox GM and his likely successor represent their personalities. Epstein rocketed to prominence in his 20s, when he became the youngest GM ever. The same restlessness and ambition that landed him the position of Red Sox GM at such a young age may now be pulling him in a new direction, away from the team for whom he grew up rooting.
Cherington, on the other hand, has taken a more deliberate route. After his tenure as co-GM, he was open about suggesting that he did not think he wasn’t sure he was ready at that point to serve in such a capacity. But, six years later, his résumé has now been rounded out. He has experienced virtually every front office position save for that of a GM. His preparation for the highest position in a baseball operations department is now thorough to the point that there is little to suggest that he is no longer ready to take his next step forward.
And so it seems fitting that, at a time when Epstein appears close to moving to his next station as a head of baseball operations, Cherington is the man whose first such opportunity may just now be arriving. If he does emerge as the next Red Sox general manager, few who have known him throughout his career will consider it a surprise.
“Ben always had that high ceiling. The personality traits, the traits that he already had, and the experience he’s had on different fronts, which is what Boston ended up doing for him, it was a great developmental curve for him,” said Huntington. “For me, without question, [those experiences] definitely make him ready to tackle significant challenges.”