UMass, Amherst alum could be next Red Sox GM
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University of Massachusetts professor Lisa Pike-Masteralexis remembers Ben Cherington sitting in her office when he was a graduate student in the sport management department, talking about his aspirations.
"I remember him sitting there saying 'I want to work for the Red Sox,'" Pike-Masteralexis said Wednesday. "He's from New Hampshire. He was a die-hard Red Sox fan. He was sitting in my office saying he wanted to get into the front office of baseball."
Not only has Cherington, now 37, achieved the goal of working for the Red Sox, he appears to be on the cusp on leading the team he grew up cheering. Cherington is the presumed front-runner to become the next general manager of the Red Sox, replacing Theo Epstein, who is reportedly leaving for the Chicago Cubs. Several media outlets have reported that Cherington has already been chosen for the post and that an announcement would come shortly.
Pike-Masteralexis has been regularly checking the news for updates and across town at Amherst College, members of the baseball program are paying similar attention. Cherington pitched for the Jeffs and their legendary coach Bill Thurston for three seasons before a torn labrum ended his playing career.
While Cherington is universally described as quiet, he makes a strong impression quickly. Thurston made Cherington a pitching coach when he was unable to play after his shoulder injury.
"When I got to know him as a coach, he asked a lot of good questions," Thurston said. "He was a good evaluator. I could see how much baseball he really knew and how much he loved the game."
After he graduated, he kept his role with the Jeffs for a year while attending the sport management program at UMass.
His first paper in Pike-Masteralexis' sports law class got her attention. The class included several lawyers, who were hoping to work in sports.
"I always grade my papers objectively. I don't have the students write their names, just a student number," she said. "When I graded the papers, I thought this first one, the highest grade, must be written by a lawyer. As it turned out, the highest grade in class was Ben's, who was also the youngest person in class.
"That threw me for a loop because I had seasoned lawyers in the class and here Ben comes out on top. That shows his attention to detail. He can make an argument and see both sides."
Pike-Masteralexis' regard for him grew throughout Cherington's time at UMass. She also works with the Diamond Management baseball agency and has stayed in touch with her former student personally, and at times professionally, since he left.
"He'll outwork anyone. He's willing to do whatever it takes. He has no sense of entitlement going into a job," Pike-Masteralexis said. "He puts his nose to the grindstone and figures out what needs to be done, no matter how many hours it takes."
Cherington's hiring would further elevate the status of the two schools in Amherst as the training ground for future general managers. In addition to Harry Dalton, who was an Amherst College alumnus and general manager for three Major League teams from 1966 to 1991, the private liberal arts school boasts former Red Sox and Montreal Expos GM Dan Duquette, and current Pittsburgh Pirates general manager Neal Huntington among its graduates.
If Cherington is hired, three of the 30 Major League Baseball general managers would have graduate degrees from the prestigious sport management program at UMass. Chris Antonetti of the Cleveland Indians was a classmate of Cherington's. Huntington, like Cherington, went from Amherst to UMass. In Pittsburgh, Huntington followed Dave Littlefield, who holds both undergraduate and graduate degrees from UMass.
Both schools have several other alumni working in lower positions in front offices throughout baseball.
Path to the Red Sox
When Cherington graduated from UMass in 1998, he took a scouting job with the Indians based on Thurston's recommendation to Huntington, who then worked for Cleveland. Both Thurston and Huntington then suggested Cherington to Duquette, who hired him in Boston in 1999.
"Those guys recommended his baseball acumen. It was clear he's very passionate about baseball and has excellent instincts for identifying talent," said Duquette, who now owns the Duquette Sports Academy in Hinsdale. "It was clear Ben had a good background, good recommendations, good passion and good skills. He gets along well with people, which is a good trait."
When the new Red Sox owners came on board in 2002, Cherington was one of two Duquette hires who were retained and he continued to rise in the organization. He worked first as farm director, then as director of player development, and helped identify and draft current players Jonathan Papelbon, Clay Buchholz, Jacoby Ellsbury and Daniel Bard.
And Cherington was an advocate for drafting Dustin Pedroia, whose body and swing had many scouts convinced he was not good enough to make the majors.
Even Thurston wasn't convinced after Pedroia's first season in the minors.
"Ben and I were talking on the phone and I said 'Geez Ben, I don't think Pedroia is going to be a major league player. His skills don't look good. He's got that big swing,'" Thurston said. "He said 'Coach, I think you're wrong.'"
Cherington quickly pointed out that Pedroia had more extra base hits than strikeouts and that his tendency was to start slowly at every level before eventually finding the groove.
"Ben had done his homework," Thurston said.
Since becoming the Red Sox second baseman, Pedroia is a three-time All-Star, and was rookie of the year in 2007 and the American League Most Valuable Player in 2008.
Cherington briefly served as a Red Sox GM once before. He and Jed Hoyer were co-general managers for 44 days in 2005 when Epstein briefly left the team over a front office dispute with team president Larry Lucchino.
Epstein won't likely be back this time and if Cherington is elevated, his former mentors expect him to thrive in the role.
"I think he and Lucchino will get along great because Lucchino is the type of guy that questions everything, kind of a devil's advocate. Ben is going to have good answers, based on good information," Thurston said. "He's extremely focused. You ask him to do something and it's done right and done on time. And he doesn't leave any stones unturned."
Pike-Masteralexis agreed.
"What Ben brings to the table is the combination of the academic, the stats, the sabermetric base, but that's not the be-all, end-all. You still have to be able to go out and watch the player and see the game," she said.
"I think Ben can bring both of those things to the table. He can bring that combination of factors together to build a team," Pike-Masteralexis added. "I've seen him as he's grown and I'd be very proud to see him in this role."
Matt Vautour can be reached at mvautour@gazettenet.com.
