A conversation with Trevor May about his former teammate Craig Breslow
What Craig Breslow was like as a teammate, and how his tenure as Red Sox chief baseball officer has gone so far.
Boston Red Sox chief baseball officer and former 12-year MLB veteran Craig Breslow is in the headlines. After failing to re-sign Alex Bregman, Breslow has once again come under fire for what has become a trend of failing to push deals across the finish line.
Breslow has had his fair share of success in his two years at the helm of the Red Sox. He traded for, and then extended Garrett Crochet, signed Aroldis Chapman and locked up Roman Anthony to a team-friendly, long-term deal, among other shrewd moves.
But his tenure, fairly or not, has been defined by some of his missteps. Breslow was at the center of the issues that led to the Red Sox trading Rafael Devers after he refused to consider playing first base. With the Red Sox in the thick of an intense postseason race at the trade deadline, he was unable to get any impact moves done, most notably failing to offer the Minnesota Twins a serious package for All-Star starter Joe Ryan.
Most recently, Bregman chose to sign with the Chicago Cubs instead of returning to Boston over a reported difference of $10 million (plus deferrals) and the Red Sox’s unwillingness to go against organizational policy and offer a full no-trade clause. Foul Territory’s A.J. Pierzynski and the Boston Globe’s Alex Speier both reported that the Red Sox failed to meet what Bregman’s camp believed his market to be and misjudged his value, allowing the Cubs to swoop in.
Breslow has become one of the most polarizing front office figures in the sport. In order to better understand him, I spoke with our very own Trevor May. While May was recovering from Tommy John surgery with the Twins during the 2017 season, he shared a clubhouse with Breslow.
Here is our full conversatio:
Answers have been lightly edited for length and clarity.
David Korn: What was Craig Breslow like as a teammate?
Trevor May: As a person, getting along with him was really easy. He’s a really smart guy. We could tell that very, very easily. He was fun to be around. He enjoyed playing and loved talking pitching. Even though I was hurt the whole year when he was with the Twins in 2017, we had our lockers next to each other so I got to pick his brain. He was a great teammate.
Korn: So you said you picked his brain on pitching stuff. What was, if you can remember, maybe a specific thing you picked up from him or a pitching philosophy you learned?
May: It was all pretty straightforward, like how to get ahead, how to use your off-speed pitches early. It was not just me though, it was a couple of the other young guys who came up just after me, too. So we were all in our second or third years. So it was a lot of like, how do you use your stuff to get ahead, how to use the edges of the zone and kind of just advancing our philosophy about throwing strikes, because that’s one of the biggest things.
He was a reliever and he ate a lot of innings, so he talked about how to stay healthy. And sometimes there was routine stuff, how to stay fresh, because he was a little older than us. He’d been around for a while. He retired not too long after that. He didn’t teach me a specific pitch, or there wasn’t a phrase he said. It was mostly just a kind of big brother energy.
Korn: Did you expect Breslow to pursue a front office role after his playing career?
May: I wouldn’t have said that I knew for sure that he wanted to do that specifically. It didn’t surprise me one bit when it turns out that he went for a, you know, a fifth floor job, an executive job. The way he was able to see the whole picture, it seemed like he was pretty in tune with the player’s union and the business side of the game as well. It makes a lot of sense that he ended up going that route.
Korn: What do you think about Breslow’s tenure as Red Sox chief baseball officer so far?
May: I think we have some big question marks around letting Rafael Devers go. That’s going to have to remain to be seen. I understand there’s a lot of pain right now looking around and not really knowing who the guy is anymore. And that’s something that I think Red Sox fans and people that follow the team are just used to. You always have your guy, and now they don’t really know who that is at the moment.
But Breslow has always been a very methodical guy. It always felt that with him, slow and steady wins the race and that he had a plan. It felt solid just talking to him, like, when he was talking about different subjects, he was very logical about them and approached them from a standpoint of not being someone that does crazy risky stuff. But he’s also going to take some shots and things that he believes will make himself better. He’ll try things, he was always open to collaboration and feedback from other people as well. So from what I’ve heard, at least for the circle around him that is there to help him with those decisions, he does include them and he does make himself available.
Baseball is, “what have you done for me lately.” It’s very common the way you can lose your goodwill with one misquote or one weird thing you say or do. And then sometimes you will see the evidence of those things panning out or not years down the road. And that’s a tough situation for a GM. It’s a kind of “damned if you do, damned if you don’t” situation. So I’m going to give him some grace there, but I give that grace to everybody.
I think we need to wait and see on a couple of the big things. But for the most part, they made their way back to the playoffs last year after trading their best player. They were better than they had been. We talked a lot on my show about how the Red Sox are not a team that rebuilds. There are a few teams like that in the Major Leagues and they’re one of them. They have bridge years, but then the next year, you bet they’re gonna be out there trying to spend money again. I would say we’re still so early in this process that it’s hard to tell if these decisions are going to lead to long term success for the Red Sox or not.
Korn: You mentioned the Devers situation. One of the biggest takeaways was that it seemed like there was a clear communication gap between Breslow and Devers. Did that aspect of how that all played out surprise you?
May: A little bit, yeah, because I always felt that Breslow was very, very approachable. He’s not a closed off guy. He’s not a person who closes his door. It would surprise me if that were something that he just suddenly started to do. He was always very open and honest and willing to answer questions, willing to have conversations with anybody. So for him to suddenly be like, “no,” or be resistant to that seems odd to me. I don’t quite find it easy to believe that it was him doing that on purpose.
But then again, miscommunications can happen too, right? Human beings, sometimes we’re not happy about something, we’ll just kind of bury it deep until it becomes a big, big, problem. Sometimes that’s too late. Even before Breslow was there, there were some times when Devers just kind of did what he wanted, no other way to really say it. And now he saw himself as a pillar of the team, which he was, and he was the highest paid guy. And so that comes with certain things, and he was seeing that he wasn’t getting those things. That can be frustrating.
But again, a dialogue is what needed to have happened. It’s much easier said than done to broach that subject, because, sometimes, you just seethe in silence for a while before you just kind of give up. I think it was less insidious from either side than anyone thinks, I think they just procrastinated so long that it came down to crunch time, and they didn’t have time to reconcile the situation. So this is what happened.
Korn: So the latest move that Breslow failed to make was re-signing Alex Bregman. It seems like the one of the biggest reasons based on some recent reporting was the Red Sox’s unwillingness to offer him a full no-trade clause. Whether or not that was the right or wrong decision, what do you think Breslow needs to do to salvage the offseason and pivot from missing out on Bregman?
May: That stubbornness sounds a little bit out of character for Breslow. I don’t know what the ownership group has to do with this. I know the way that they operate too, they like to be a little bit more vocal in these conversations. Play a little bit of hard ball.
I think that moving forward, one thing they’re going to be leaning really heavily on is the young guys, which they should be doing anyways. But how you replace Bregman, I don’t know. It might need to be a savvy trade. I would say maybe stop gap this thing with Nolan Arenado, but he isn’t there anymore. They already got the two other guys from St. Louis, might as well go for the trifecta. I don’t know what they do with third base, the Japanese free agents that were available are no longer there. It’s a tough situation. That’s why Red Sox fans are so angry.
It just made too much sense to get the Bregman deal done, and for it not to be done, it sounds like they might just have to try some guys out. Maybe there’s someone in the trade market that I’m not thinking of, but that would probably be the place they got to go to, because it’s looking pretty thin out there in the free agency.