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Former Red Sox adviser Jeremy Kapstein was a major player

Jeremy Kapstein (right) with manager John Farrell in June.Jim Davis/Globe Staff

About two weeks ago, the Red Sox quietly parted ways with one of the most significant figures in baseball history — Jeremy Kapstein — when Dave Dombrowski didn’t renew his contract after 14 years as a senior adviser of baseball projects.

Kapstein, known to many fans as the man with the yellow headphones behind home plate at Fenway Park, was brought to the organization by Larry Lucchino, who had used Kapstein as an adviser in San Diego for many years. Kapstein reported to Lucchino, who has since stepped down as team president, replaced by Sam Kennedy.

“I’m very disappointed,” Kapstein said, “but I am grateful for the 14 seasons I was part of a great Red Sox organization. The many close friends I’ve made both off and on the field, and within the organization and throughout Red Sox Nation, are truly a treasure for me. I know the Red Sox have a great future.”

“I have the utmost respect for Jeremy for all that he’s accomplished in this game,” said Dombrowski. “He’s a friend and he’s helped me a great deal over the ears. I think the world of him. He’s a good man and I know he did so much to help the Red Sox over the years and I know most of his work had been with Larry Lucchino. As I was putting together our scouting staff I just couldn’t fit a full-time role for him.”


Kapstein, a former player agent, once represented, among others, Fred Lynn, Carlton Fisk, Rick Burleson, Jerry Remy, Joe Rudi, Rollie Fingers, Steve Garvey, Dave Concepcion, Tony Perez, Don Baylor, Dusty Baker, and Ken Brett, some of the biggest names in the game in the 1970s.

Kapstein was one of the first to use statistics to defend his players in arbitration, and he still owns one of the best records against the owners, including some classic battles with the A’s eccentric Charles O. Finley. Kapstein was considered one the greatest negotiators of his time. He was a pioneer, negotiating some of the first guaranteed contracts and no-trade clauses.


In 1989, Kapstein, a Rhode Islander, left his agent business to run the Padres, whom he turned around in a hurry. In 1990, he sold the Padres, on behalf of owner Joan Kroc, his mother-in-law, to Tom Werner for $75 million, which at the time was a hefty amount.

Kapstein then spent more than a decade running a homeless mission in San Diego, helping people get back on their feet, providing financial and moral support.

He returned to the Padres’ board of directors in 1997, and as a senior adviser to Lucchino with a new ownership group. Then Kapstein followed Lucchino to Boston, where in 2005, after general manager Theo Epstein had left the organization following a clash with Lucchino, Kapstein helped orchestrate the Mike Lowell/Josh Beckett deal.

“If it wasn’t for Jerry, we never would have got the deal done,” Marlins executive Jack McKeon said at the time.

Kapstein said on Nov. 27, 2005, shortly after the deal was made, “Mike Lowell is an excellent clubhouse guy, a great kid who everyone believes will rebound from his year last season. He’s an excellent fielder and his hitting style is as such he’s going to hit some balls off the Wall and over it. Josh Beckett is a front-line starter who keeps getting better.”


Some baseball people couldn’t believe the Red Sox took Lowell, who went on to be named MVP of the World Series in 2007. Kapstein was right on both players.

Kapstein had the uncanny ability to evaluate players and situations. He could tell you everything that was right and wrong with a player, and his percentage of being right was astonishing. Kapstein took great interest in the Red Sox farm system and always had the most honest evaluation of its players.

Kapstein graduated from Harvard and Boston College Law School. He served as a Naval judge in Washington. He was a researcher on ABC’s college football game of the week with Chris Schenkel and Bud Wilkinson, and also kept stats and did pregame research for Keith Jackson, Frank Gifford, Howard Cosell, and Don Meredith on “Monday Night Football,” introducing the statistics of time of possession and third-down conversions to the broadcasts.

Many in the Red Sox organization expected Kapstein to be the choice to run the PawSox, but Lucchino, now the principal owner of that team, had made other plans.

Kapstein would have continued the family atmosphere fostered by previous owner Ben Mondor, and likely averted the public relations nightmare Lucchino has encountered in his quest to move the team from McCoy Stadium to Providence.

Kapstein also made an unsuccessful run for lieutenant governor in Rhode Island, and was the first to suggest in his campaign that lawmakers not devote $75 million to Curt Schilling’s 38 Studios, as he saw numerous red flags. The business went belly-up.


Kapstein isn’t done.

“I certainly want to continue in baseball and make a contribution wherever that might be,” he said. “I love the game and the people in the game.”

Ruben Amaro Jr. was fired by the Phillies in September.AP


Amaro familiar with Sox players

Ruben Amaro Jr. will begin his second baseball career in a pretty nice situation. As first base and outfield coach for the Red Sox, Amaro will inherit one of the best defensive outfields in baseball.

He already has tremendous knowledge of his new players. After all, as GM of the Phillies, he tried to obtain some of them for Cole Hamels. Mookie Betts was the apple of Amaro’s eye. Jackie Bradley Jr. was another Red Sox player the Phillies discussed. The others were Blake Swihart, Xander Bogaerts, and young outfielder Manuel Margot, who will be in camp and could play as high as Triple A in 2016.

“We certainly did a lot of scouting and eyeballing of them,” Amaro said. “To have that information is helpful, but I look forward to working with them every day and getting to know them as people and what makes them tick.

“The Mookie, Bradley Jr., and [Rusney] Castillo group are obviously very talented. I’ve contacted them to begin the process of introducing myself to them and seeing what we can do to improve whatever is needed.

“I think the fun part and the important part is being able to get together and discuss things as a group or individually and really break things down and discuss the game. That’s the joy of it. I’ve always had a very good relationship with the players. I was probably in the clubhouse more in my earlier years as a GM than I was later, but it was still something I enjoyed doing.”


Did Amaro ever come close to acquiring them?

“That’s not something I really want to discuss,” he said. “Through the process, I had so much admiration and respect for Ben Cherington. Out of respect for Ben I wouldn’t reveal those conversations, nor would I now in my current position.”

Amaro eventually traded Hamels to the Rangers for a haul of impressive prospects.

“Ruben is smart,” said Diamondbacks chief of baseball Tony La Russa. “He can instruct, teach, do anything.”

Ex-Phillies closer Brad Lidge recently spoke about Amaro spending a lot of time in the clubhouse talking with players. In that respect, Amaro should have no problem with his change of hats. Amaro played the outfield as a converted infielder over eight big league seasons.

Apropos of nothing

1. The situation with the Marlins gets worse by the minute. Don Mattingly is the latest to dive into a scene that usually doesn’t end well. Mattingly, just fired by the Dodgers, wanted to stay in the game, so Marlins owner Jeffrey Loria decided he would be the eighth manager he’d hired in the last six years. Dan Jennings was fired last week after being told he could return to his GM job from the role of interim manager. Loria probably did Jennings a favor. Jennings, who has two years left on his contract and is owed about $2 million, wanted to stay on as manager feeling he had gotten the hang of it, but he was kicked back upstairs, told he’d be the GM, and then got fired. “[Loria] fired his best friend,” said former Marlins manager Ozzie Guillen, who is also still being paid by Loria.

2. Alex Anthopoulos walking away from a five-year extension to remain GM in Toronto was the shocker of the week. Many thought new team president Mark Shapiro would concentrate on business, but evidently his role in baseball decisions will be greater than anticipated. In the end, it was no different than the Dave Dombrowski-Ben Cherington dynamic with the Red Sox, where Cherington couldn’t work under someone who would have the final say. Anthopoulos, who orchestrated trade-deadline deals for Troy Tulowitzki and David Price, made the Blue Jays the most exciting team over the last two months of the season. There are no GM openings, but Anthopoulos will certainly figure into future jobs, such as Cincinnati, where Walt Jocketty plans to retire after next season. Anthopoulos said his departure had nothing to do with Shapiro, but you have to wonder.

3. Bob Nightengale of USA Today wrote a compelling piece on the lack of diversity in baseball. There will no African-American managers in 2016 if the Dodgers don’t hire one. There will be only one minority manager, Atlanta’s Fredi Gonzalez. There are only four minority front office executives. The story links the lack of diversity to the use of analytics. As GMs rely more on analytics, they tend to hire managers of a similar mind-set. Does that mean minorities are not analytical? That seems to be the implication. It has shut out deserving candidates such as Demarlo Hale, Alex Cora, and even second and third chances for Dusty Baker and Don Baylor. It’s baseball’s next big problem.

4. Two players that could be big in free agency are Toronto’s Marco Estrada and Texas’s Yovani Gallardo. You hear their names a lot as possible affordable arms. Estrada had a breakout season, while Gallardo left Milwaukee and pitched well in Texas. Both teams are interested in re-signing them.

Updates on nine

1. Ben Cherington, former general manager, Red Sox — He has taken a teaching job in sports management at Columbia University. There are reports that the Pirates are trying to add him to their front office. New Blue Jays president Mark Shapiro has always enjoyed a good relationship with Cherington, so you wonder if that would work. But it would require Cherington, who turned down offers to interview in Philadelphia and Seattle, to reassess whether he’d want to work under someone in a GM role.

2. Ron Gardenhire, former manager, Twins — Gardenhire hasn’t been able to catch a break since leaving the Twins after the 2013 season. He’s been on the fringe of a couple of jobs and had two interviews with the Padres before they went with relative unknown Andy Green. According to one major league source, “Gardie can take certain direction with analytics and numbers, but he’s his own man. He’ll manage the game the way he sees fit, and not by how someone in the front office sees it. He always had that freedom in Minnesota.”

3. Ben Zobrist, INF/OF, Royals — No doubt Zobrist is a valuable player who can help at second base, shortstop, third base, or the outfield, but there’s a problem. “It’s Father Time,” said one American League executive. “Ben is 35 years old. He keeps in great shape and does the job, but he’s not someone you’re going to devote big dollars to over a long-term deal.” Agent Alan Nero sees it differently. Nero feels Zobrist can get a three- or four-year deal on the market. Nero has not discussed Zobrist with the Royals yet, and doesn’t know whether they are open to retaining him.

4. Torii Hunter, former OF — Now that Hunter has retired, the time will tick off on when he will consider a managing job. He’ll spend the next couple of years watching his kids play major college sports, but afterward teams will come after Hunter. He often told Twins GM Terry Ryan he aspired to be a GM.

5. Dave Magadan, hitting coach — Magadan and the Rangers parted ways last month after three years. The ex-Red Sox hitting coach is entertaining the thought of working closer to his Florida home and also a scouting/front office opportunity. He’s already had a couple of conversations with teams. Magadan thought manager Jeff Banister wanted his own hitting coach, even though the Rangers finished third in the majors in runs. “I don’t blame Jeff for wanting his own guy,” said Magadan. “I think Jeff and Jon [Daniels, the GM] and I just saw things differently.”

6. Josh Hamilton, OF, Rangers — Magadan said that if Hamilton ever gets healthy “he still has the ability to be what he was. His bat speed is still there, but when you’re injured and you’re not right, it’s awfully tough to get there. But if he gets healthy, he can be a force offensively. It just seemed every time he was about to get there, something would pop up.”

7. Dave Wallace, pitching coach, Orioles — Wallace will return after manager Buck Showalter asked him to stay, according to a major league source. It was a trying season for the Orioles pitching staff, and it may get worse if Wei-Yin Chen, their most consistent pitcher, leaves as a free agent. The other concern is managing prospect Dylan Bundy’s innings. Bundy has been injured off and on for two seasons, so asking him to pitch a lot of innings is probably not in the cards.

8. Gabe Kapler, farm director, Dodgers — Kapler remains the leading candidate for the Dodgers managing job, according to team sources. The former Red Sox outfielder speaks the same language as team president Andrew Friedman, so they’d be a good match. Kapler managed one season for the Red Sox in Greenville and drew rave reviews. A lack of major league managing experience no longer seems to be a factor in landing the job. Cubs bench coach Dave Martinez’s name also pops up quite a bit.

9. John Valentin, assistant hitting coach, Dodgers — Valentin remains in limbo, awaiting word on whether he’ll survive or get rehired by the new manager. It’s not known whether Don Mattingly will take some of his Dodgers staff to Miami. Rick Honeycutt and Tim Wallach could be possible Marlins coaches.

Extra innings

From the Bill Chuck files — “Gerardo Parra and Yoenis Cespedes each hit .291 and had an OBP of .328; Parra hit 14 homers and whiffed 92 times, while Cespedes had 35 HRs and 141 K’s.” Also, “Two division champs had the highest batting averages against the AL East in 2015: the Royals (.277) and Rangers (.275). But the Mets only hit .220.” . . . Happy birthday, Coco Crisp (36) and Carlos Rodriguez (48).

Power play

A pair of young sluggers, Rockies third baseman Nolan Arenado and Nationals outfielder Bryce Harper, each belted 42 homers this season, putting them in select company. Only 28 players in baseball history have hit that many homers at age 24 or younger, and 15 went on to be enshrined in the Hall of Fame.

Compiled by Richard McSweeney

Nick Cafardo can be reached at cafardo@globe.com. Follow him on Twitter @nickcafardo. Material from interviews, wire services, other beat writers, and league and team sources was used in this report.