The mark of a good coach isn't necessarily turning a bunch of nobodies into superstars, but rather consistently leaving players a little better than he found them. For the Boston Red Sox, Craig Breslow's longtime friend Andrew Bailey has been tasked with pumping up the members of the pitching staff to be their best selves.
After being the only surviving member from Boston's version of the Red Wedding when Alex Cora was fired, one would have thought that Bailey was excelling in his role. And while the Red Sox's offense has been a much greater issue than the pitching staff in 2026, things like Brayan Bello's stagnation and then dramatic regression are not feathers in Bailey's cap.
Again, this isn't about turning every player into a star. Bello is a limited pitcher who relies on his sinker to generate ground balls but has no real put-away pitch. But Bailey still failed to enhance that canvas to turn him into a productive member of the rotation.
Perhaps most damning are the pitchers who have experienced dramatic improvement as soon as they left Bailey's side. Kyle Harrison will haunt the Red Sox for a very long time, but he's not alone. Dustin May is right up there with Harrison as a guy who has reached new heights as soon as he left Boston.
WHO are second and third? pic.twitter.com/RxjIDNLoup
— Sox Savant (@Sox_Savant) June 15, 2026
Even Walker Buehler, who looked like toast in a Red Sox uniform, has been reborn this season. As of June 20, May's FIP has fallen from 5.39 during his time with Boston to 3.32 this year in St. Louis. Buehler posted a 5.89 FIP as a member of the Red Sox last year, and now owns a 3.28 mark this year in San Diego.
Andrew Bailey's place on the Red Sox coaching staff is a prime example of Craig Breslow's nepotism
As controversial as it was to fire Cora and the rest of the coaching staff, it's hard to objectively state that Bailey wasn't just as much of a problem as everyone else. Of course, the ultimate failing lies on Breslow's shoulders because he's the one who assembled the flawed and underachieving roster.
However, Bailey remaining with the team has as much to do with Breslow trying to circle the wagons and create an echo chamber of yes men around his analytics-heavy approach.
The two men have been friends for a long time. They've wanted to work together forever, and that's in large part because they see things the same.
And there's a case to be made for a heavy use of analytics, especially when it comes to developing pitchers, but one can't completely ignore the human element either. The Red Sox have, and it's been evident time and time again since Breslow took the reins.
This is yet another example of the embattled executive's lack of communication skills working to the team's detriment. It's tough to tell a friend that his performance isn't satisfactory and make hard decisions, but that's exactly what Breslow needed to do. He didn't, and Breslow sent these hurlers packing, probably with Bailey's input considered, and now he is watching them thrive in greener pastures.
For Red Sox fans, the Breslow era can't come to a close soon enough. The hubris, the ego, the nepotism, and the lack of communication have cost the team greatly, and there will be no brighter days until he and his henchmen are gone.
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