Craig Breslow’s Former Boss Praises Red Sox’s ‘Conviction’ With Bold Moves

Jed Hoyer knows what it’s like to be in Craig Breslow’s shoes.

Hoyer, who worked in the Boston Red Sox’s front office from 2002 to 2009 and served as Theo Epstein’s assistant general manager, followed Epstein to the Chicago Cubs in 2012. He took over for Epstein as the Cubs’ president of baseball operations after the 2020 season.

In his first season on the job (2021), Hoyer boldly shook things up in Wrigleyville by trading much of the team’s 2016 championship core, including Anthony Rizzo, Javier Báez and Kris Bryant.

Breslow was Hoyer’s assistant GM at the time, learning important lessons in dealmaking and gaining first-hand experience in how to make franchise-altering moves.

Since leaving Chicago for Boston in late 2023, Breslow has made similarly impactful moves. He traded for Garrett Crochet, signed Alex Bregman and traded franchise icon Rafael Devers in a span of six months, completely reshaping the Red Sox.

While watching Breslow from afar, Hoyer has been impressed by his former colleague’s big swings.

“He’s been bold with the (Garrett) Crochet deal, and obviously with the Devers deal, I loved the conviction he showed on that deal,” Hoyer told Jen McCaffrey of The Athletic (subscription required).

It’s been roughly 21 months since Craig Breslow worked for the Cubs, but his five seasons in Chicago under Jed Hoyer were formative years for him as a front-office executive and helped shape what he's done in Boston.https://t.co/F67HBboXUx

— Jen McCaffrey (@jcmccaffrey) July 21, 2025

Hoyer worked for Boston when the team parted ways with fan favorites like Nomar Garciaparra, Manny Ramirez, Pedro Martinez and Johnny Damon, so he knows how hard and sometimes unpopular those moves can be, even if they help the team in the long run.

While Breslow was initially criticized for trading Devers to the San Francisco Giants in the middle of his prime, the move already appears to be paying off. The Red Sox are 17-12 since the trade — tied for the fourth-best record in baseball — and may have some more aggressive moves up their sleeve with the MLB Trade Deadline coming up.

“He felt like he was doing the absolute right thing for the franchise, and those are hard decisions,” Hoyer told McCaffrey. “When I see other executives make decisions like that, I have so much respect because I know what goes into it from a personal standpoint.”

Meanwhile, the Cubs have reloaded under Hoyer and are once again among the best teams in baseball. They took two of three from the Red Sox at Wrigley Field over the weekend and are tied for the third-best record in MLB entering play on Tuesday.

Both Breslow and Hoyer have their teams in playoff position. While Breslow no longer works for Chicago, his old boss still respects what he’s accomplished so far in Boston.

“I learned a lot from him. Hopefully, he learned a lot from us,” Hoyer told McCaffrey. “I think he’s done a fantastic job. And I think he’s going to be doing this job at a high level for a long time. He’s made really hard decisions.”