Red Sox World Series Champ Explains What Craig Breslow Brings To Boston

Red Sox president and CEO Sam Kennedy cited the “resounding character references” from Craig Breslow’s former teammates as being a distinguishing factor in Boston’s search for a head of baseball operations.

David Ortiz, Dustin Pedroia, David Ross, Brock Holt and Kevin Youkilis were among those who spoke highly of Breslow, according to Kennedy, which played a role in Boston earlier this week hiring the former Red Sox pitcher as its new chief baseball officer.

“Craig knows what it takes to be successful in Boston and he’s up for the challenge,” Kennedy said, per a press release.

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Ryan Dempster, who shared the Red Sox clubhouse with Breslow during Boston’s 2013 World Series-winning season, agrees. He witnessed Breslow’s potential firsthand during their playing days and then again in recent years as Breslow worked in the Chicago Cubs front office.

“I think it’s a great hire,” Dempster, who now works as an analyst on Cubs broadcasts, said this week on MassLive’s “Fenway Rundown” podcast. “I think he’s incredibly smart, as everyone knows. He’s intelligent, knows the ins and outs of a lot of different aspects of the game, how the business works. The thing I love about Bres a lot is he’s a good listener, and I think if you’re going to be in that kind of position, A) You’re going to have to listen to a lot of different things and how do you digest all of that information. And he was that way as a teammate, front office with the Cubs. I had a lot of conversations with him. I feel like he’s hugely responsible for the pitching growth in the Cubs organization, which wasn’t there for 10 years. He played a huge part in that.”

Theo Epstein, who brought championship glory to both Boston and Chicago, handpicked Breslow to join the Cubs front office in 2019, opening the door for what turned out to be a rapid ascent. Breslow, a Yale graduate who majored in molecular biophysics and biochemistry, is considered one of the smartest men in sports, which Epstein clearly sought to leverage by giving the former hurler the freedom to more or less define his own role.

Breslow obviously knows baseball. And his experience as a player could benefit the Red Sox, as well. He has a unique perspective, having seen both sides of the coin — the on-field side and the business side.

But Breslow’s communication skills, in addition to his intellect, shouldn’t go unnoticed. He’s able to connect with people, including players, on a different level, according to Dempster, thereby fostering a collaborative and productive environment.

“He’s an amazing listener. I think that’s a powerful thing to have,” Dempster said on the “Fenway Rundown” podcast. “He might not have all the answers, and he’s going to find out what they are. And I think being in those shoes (as a player), now when he makes decisions, there is a little bit of that. Whether it’s subconsciously, or whatever it is, guys immediately have a little bit more of, ‘Well, he understands. He played.’ It doesn’t mean that somebody in that position that hasn’t played can’t pull those off, too, and those usually happen because those people are really good at communicating with the players.

” … I think Craig has that, and he was a player. So, I think he has it two-fold, and he’s got to just go out there and execute it and not be afraid to make the tough choice sometimes, go out on a limb for something every once in a while. Especially when you’re playing in a town and a city like Boston, with that fan base, playing it safe doesn’t always work. You’ve got to go out there and make a stand and say, ‘This is what we’re trying to do. We’re the Boston Red Sox.’ And I feel like he’s built for this moment. It’s pretty awesome. I’m super happy for him.”

Basically, Breslow has instant credibility thanks to his playing credentials. And he’s done nothing but boost his résumé since hanging up the spikes.

The hire isn’t without risks, obviously, since Breslow never has overseen an entire baseball operations department. But the potential reward was too much for Boston to pass up in trying to replace Chaim Bloom.

“I thought the Red Sox did a great job, obviously, with hiring someone who’s A) been a Boston Red Sox, which is pretty awesome,” Dempster said. “An ex-player now is running baseball ops — a World Series champion, he played five years in a Red Sox uniform. Yeah, I think it’s got a lot of upside and they’re going to be pleasantly surprised, I think. The people in Boston will like what he brings to the table.”

Breslow, 43, is the fourth former Red Sox player to lead the franchise’s baseball operations efforts. He’s the first since Haywood Sullivan served as Boston’s general manager from 1978-83.