Things haven't gone exactly as the Boston Red Sox hoped after bringing Craig Breslow aboard to run their front office in October of 2023. A member of Boston's 2013 World Series-winning club, Breslow was brought in to once again make the Red Sox into a formidable American League contender. Instead, over a season and a half, they've been a .500 team, at best.
Breslow was supposed to be the next baseball executive wunderkind. Ivy League educated and with a 12-year MLB career under his belt, the former relief pitcher was supposed to merge cutting-edge analytics with the innate feel for the game that only an ex-player could bring.
And while that best-case scenario might still come to fruition, it doesn't seem likely. Breslow's been accused of being cold and robotic, which makes sense given the rumor that the Red Sox heavily utilized AI interviews for top baseball operations job candidates.
The shocking trade of superstar Rafael Devers is certainly the biggest black mark on Breslow and the Red Sox, with some considering it a fireable offense. There are many more wrong turns the organization has made, some of which predate Breslow, though Breslow certainly threw gas on the fire and made it worse than it needed to be.
4 expectations the Red Sox got completely wrong under Craig Breslow
1. Communication
The biggest example, though not the only one, is what happened with Devers. Sure, Breslow wasn't running the show when Devers inked his 10-year, $313.5 million deal, but the organization as a whole committed to Devers as its franchise player. It should have been a given, then, that Breslow treat him as such.
The MLB is different than the NBA or even the NFL as far as how much input a team's star has over personnel moves. No one is mistaking Devers' role with that of LeBron James, for example. However, when Breslow signed Alex Bregman, a star-level player who happened to play the same position as Devers, it shouldn't have come as a surprise to the incumbent star.
But that's exactly what happened, and from there, every tiff that followed was just another tug at the thread until everything completely unraveled. It didn't have to be this way, and while it is impossible to know what happened behind the scenes, it seems like someone should have talked some sense into Breslow before pulling the trigger on the Bregman signing. That is, if he actually communicated his plans to anyone else in the organization.
2. Emotional Intelligence
Similar to the communication breakdowns, Breslow has shown an incredible lack of emotional intelligence. Breslow owns his cold and robotic reputation for good reason.
Going back to Devers and Bregman, one would expect this kind of move from an analytically focused executive who doesn't have a background playing the game and believes players can simply change positions on the fly like in a video game.
As a former player, Breslow should know better. Every player on a ball club, from the face of the franchise to the last man on the bench, has spent nearly his entire life as the best player whenever he steps on the field. As a result, none want to look bad as their put in a position where they are not comfortable.
You'd expect this kind of behavior from a Wall Street dealmaker or a bean-counting accountant, not from a guy whose big league career lasted over a decade. This is something San Francisco Giants' executive Buster Posey understands, which is why Devers had no problem agreeing to play first base in the Bay Area.
3. Strategic Planning
One of the most important things an executive can do is look at the roster and think two or three moves into the future. They need to come up with a vision for what the team should look like and know when and where to pivot when things inevitably go awry.
Looking at the Red Sox, especially recently, Breslow is severely lacking. Take second base, for example. While Breslow clearly wanted to make room for Boston's numerous top prospects, he didn't plan for the possibility that they might struggle.
Kristian Campbell is a perfect example. The 23-year-old only logged 19 games at Triple-A Worcester last season before being anointed the opening day second baseman on the big league club. 67 games and some serious struggles later, he's now back in Triple-A trying to figure things out.
Instead, Breslow replaced his All-Star third baseman with another All-Star third baseman while leaving his top prospect without a veteran safety net. The book is far from written on Campbell, but the start was certainly inauspicious, and that's on Breslow and his failure to prepare.
Or try this one on for size. Breslow has identified some clear needs his club must tend to via the trade market, but understands that in early June, no one is going to be picking up the phone for serious trade discussions. So then why did Breslow make a blockbuster trade on June 15, just to leave his club in the mud for the next six weeks?
By the time Breslow starts hitting the phones and trying to get the Red Sox some help, it may already be too late. Meanwhile, how much more could he have gotten for Devers if he had actually opened up the negotiations for public bidding?
Everything in Breslow's tenure to this point has been a reaction, rather than a step forward on a quest to complete a specific vision. That's a recipe for failure.
4. Failing to break through and capitalize on the talent stockpile
Over recent years, the Red Sox have put together impressive collections of talent just to watch things fizzle out. Whether it's been blowing up a perfectly good core by trading Mookie Betts away, failing to put the finishing touches on a solid roster looking to take the next step, or failing at balancing prospect hoarding with leaving the system barren, Red Sox executives haven't made the most of what's in front of them.
To be fair, owner John Henry is partly to blame as the billionaire has been more enamored with his other toys, such as the English Premier League's Liverpool, than the Red Sox over the past couple of years, leading to the financial goliath acting more like a mid-market team.
With rumors beginning to swirl that Boston may trade controllable veterans like Jarren Duran, who is in the midst of a down year following last year's All-Star campaign, one has to wonder if Breslow will repeat the sins of the past.
Boston already has a top-ranked farm system, and while some of those players are knocking on the door of the big league roster, it's important that the club doesn't cut off their nose to spite their face.
If Boston wants to retool by jettisoning veterans on expiring deals who don't have a future with the club, no one would complain. But trading big league assets with control remaining when they are underperforming is classic mismanagement.
At the same time, trading away some prospects to supplement to big league roster should be a priority for a team that has perennial playoff aspirations. To his credit, Breslow did follow that path in the Garrett Crochet deal.
Still, more must be done if Breslow is to avoid the sins of the past, and so far, he's done little to show that he's not walking the same misguided path.