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Dom Amore: Craig Breslow reimagined Red Sox with bold moves. It's no shock to ex-teammates.

Dom Amore, Hartford Courant on

Published in Baseball

HARTFORD, Conn. — After a frustrating 2 1/2 months, the Red Sox falling a low as five games under .500 and more than 10 games out of first place, signs of life appeared. And then on June 15, they completed a three-game sweep of the Yankees at Fenway Park, allowing only four runs.

That night, with much of New England beginning to believe again, the word came out: Craig Breslow, the chief baseball officer, or GM, sent the franchise’s long-time star, Rafael Devers, to San Francisco for mostly unproven talent.

“I acknowledge that on paper, we’re not going to have the same lineup that we did,” Breslow explained later. “But this isn’t about the game that is played on paper. This is about the game that’s played on the field. We are trying to put together the most functional and complete team that we can.

“… I do think that there is a real chance that at the end of the season, when we’re looking back, we’ll have won more games than we otherwise would have.”

It may have been surprising, shocking to many, not only trading Devers, which felt like a white flag, but for Breslow, the Yale-educated executive often accused of over-reliance on analytics, to acknowledge the chemistry piece as critical to building a winning team.

But to the guys who’ve known him from his days at Trumbull High, it’s pure Craig Breslow in action.

“Craig has always trusted his instincts, on and off the field,” says Mike Buswell, who played with Breslow on Trumbull’s 1998 state championship team. “He’s the ultimate example of someone who bets on himself, and that’s exactly what’s made him successful. Some of the moves you’ve seen him make may come across as surprising or knee-jerk moves, but that’s never what they are if you know Craig Breslow. Craig is always playing chess while others are playing checkers.”

Sure, the Red Sox initially felt the absence of Devers’ departure, losing eight of 12 following the trade, but then the fruits of that and Breslow’s other moves began to ripen. They won 10 in a row, 12 of 13 games heading into the All-Star Break, and with the best record in MLB (24-11) since June 4, have surged into the thick of the AL East and wild-card races.

If there was an executive of the year named at the All-Star break, Breslow would be it. With the trade deadline two weeks away, the Red Sox are baseball’s hottest team, and they have a hot hand at the craps table.

“Last year, when he was making the moves to get pitching, that was right up his alley,” said Donny Anicelle, another Trumbull teammate. “Pitching and defense wins championships, we grew up with that. Fundamentals, our coach (Jerry McDougall) drilled that into our heads. That’s what wins.”

Three of Breslow’s offseason acquisitions — Alex Bregman, Garrett Crochet and Aroldis Chapman — made the AL’s All-Star roster, and he picked the right time to promote from the organization’s enviable stockpile of young talent, namely Roman Anthony, who’s hitting .341 in July, and Marcelo Mayer. Kristian Campbell, the third of Boston’s top prospects, made the team out of spring training, started strong but struggled and was sent back down.

Breslow traded other prospects to get Crochet (10-4, 2.23 ERA) from the lowly White Sox.

 

Breslow signed Bregman, who played on championship teams with Houston, but was also involved in the Astros sign-stealing scandal, to a three-year, $120 million contract, even though he played third base, Devers’ position. Devers balked at moving to play first base, and controversy lingered leading up to the trade.

“He has some of the best young prospects in the game,” Buswell said, now vice chairman of the Trumbull Town Council and a travel ball coach. “He does not want them poisoned by a disgruntled veteran. Craig is the ultimate clubhouse guy. At the end of his playing career, teams wanted him around in a mentorship role for the younger guys in the locker room. If he feels he has a piece that is not going to fit with his master plan, he’s going to address it.”

Bregman, hitting .298 with 11 homers, is coming back from an injury. Chapman, nearing the end of a storied career, was procured for one year, $10.5 million, and he’s shown his fastball still has its old zip. Breslow and his scouts stole a first-string catcher, Carlos Narvaez, from the Yankees, who’d had him in their minor league system since 2015.

Breslow’s teammates at Trumbull also included Jamie D’Antona, who later played in the majors with Arizona. The ace pitcher, Breslow threw 159 pitches, his teammates vividly recall, to win the semifinal game in 1998, then with a couple of rainy days in between, returned to the mound to beat Masuk-Monroe in the Class LL final, his third complete game of the tournament. “We all went on the bus to Muzzy Field in Bristol knowing we were going to win the state championship if the ball was in his hands,” Busman said.

Though he had offers from major programs, Breslow, a lefty, stuck with his plan to go to Yale, where he double-majored in molecular biophysics and biochemistry in preparation for a career in medicine. Taken by Milwaukee in the 26th round of the 2002 MLB draft, Breslow deferred med school and pitched in the majors from 2005-17, was 5-2 with a 1.81 ERA for the World Series-winning Red Sox in 2013. Along the way, he made a study of innovations in pitching biomechanics and in 2010 the Sporting News had him atop a list of “smartest athletes.”

After his playing career ended, he joined Theo Epstein, also a Yale grad, in the Cubs’ organization as director of strategic initiatives. When the Red Sox parted ways with Chaim Bloom, yes, another Yale grad, after back-to-back last-place finishes in 2023, they took a while to fill the position before hiring Breslow.

“I know what it takes to win here and I’m willing to make the hard decisions necessary to deliver,” Breslow said when he was introduced.

In his first season with Breslow running baseball operations, the Red Sox were 81-81. With ownership, he has stood behind manager Alex Cora, who guided the franchise’s last championship team in 2018, and managed the rich farm system Boston inherited from Bloom.

Now Breslow, 44, has a chance to lead the Red Sox from worst to first with a few more of the right moves this month, and free of Devers’ burdensome contract, he’s well-positioned. To be successful in major league sports takes a willingness to make bold decisions, to make unpopular decisions, ignore the initial firestorm and stick to plan. The latest buzz has another fan favorite, outfielder Jarren Duran, possibly headed out of Boston to fill needs, maybe bolster the bullpen. Whatever he does, and whatever comes with it, Breslow can be counted upon for having the courage of his convictions.

“He has to be playing with a little bit of analytics, but also a little bit of his gut, and I don’t think his gut has ever served him bad,” said Anicelle, now a dentist in West Hartford. “He has a conviction to know that what he’s trying to do will be successful. He’s not afraid. He’s not afraid of anything.”


©2025 Hartford Courant. Visit courant.com. Distributed by Tribune Content Agency, LLC.

 

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