CHICAGO — Jed Hoyer knows what it’s like to make unpopular, franchise-altering trades.
At the 2021 trade deadline, fans lambasted the Chicago Cubs president of baseball operations for breaking up a beloved group of World Series-winning players. Hoyer viewed the trades at the time as painful but necessary moves.
In that vein, he applauded Boston Red Sox chief baseball officer Craig Breslow with unusual candor for Breslow’s “conviction” in pulling off one of baseball’s most shocking trades this season. Last month, Breslow traded Rafael Devers to the San Francisco Giants in exchange for pitchers Kyle Harrison and Jordan Hicks and prospects James Tibbs and Jose Bello.
“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 said Sunday as the Red Sox avoided a sweep by the Cubs with a 6-1 win.
In Chicago at the 2021 deadline, Hoyer made major moves in an attempt to turn around the Cubs franchise, but it involved some uncomfortable realities. Hoyer understood when he took over for Theo Epstein after the 2020 season that he’d have to bear the burden of change in Chicago. He knew it would be wildly unpopular trading Anthony Rizzo to the New York Yankees, Javier Báez to the New York Mets and Kris Bryant to the Giants in the span of two days, all with an eye toward the future.
The biggest return among those trades was getting then-prospect Pete Crow-Armstrong from the Mets. Crow-Armstrong is vying for NL MVP as the Cubs surge, nearly 20 games over .500 and in first place in the National League Central.
During that time of tumultuous change in Chicago, Breslow served as an assistant general manager under Hoyer and was at the center of those moves as part of a small, trusted inner circle for Hoyer.
Hoyer described Breslow’s role in helping retool the Cubs organization, drawing some parallels to what Breslow is doing in Boston.
“He was a big part of the decision to trade away our core World Series guys,” Hoyer said of Breslow. “I think he saw the reaction fan-base-wise — there was real frustration and anger — but ultimately, we as a group made the decision that it was time. It was time to reset and bring in new talent and put the organization in a different direction. He saw that as the right thing to do at the time.”
It’s been roughly 21 months since Breslow worked for the Cubs, but in so many ways, his five seasons in Chicago were formative years for him as a front-office executive.
More than most, Hoyer can relate to the hard decisions Breslow has felt necessary to make in Boston.
Hoyer has gone from Breslow’s mentor in Chicago to a rival executive in different leagues, but he has watched from afar as Breslow has been aggressive in changing the front-office structure, retooling the roster with major trades and revamping the organization’s pitching infrastructure to bring the Red Sox back into contention.
With the second half underway, the Red Sox are fighting for a spot in the playoffs for the first time since 2021. Breslow has some major decisions to make as his second trade deadline as chief baseball officer of the Red Sox approaches next week, but he has already proved a willingness to be bold.
Not every trade works out; that’s a reality of the business. Many across baseball criticized Breslow for the Devers deal. Hoyer saw the move as an opportunity that even experienced executives might have shied away from.
“He felt like he was doing the absolute right thing for the franchise, and those are hard decisions,” Hoyer said of the deal. “When you’re doing something you know in the short term could frustrate some people but you totally believe is in the best interest of the organization, those are hard decisions. 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.”
Hoyer, a New Hampshire native who went to Wesleyan University in Connecticut and spent seven seasons in the Red Sox front office from 2002 to 2009, working under Epstein and serving as co-general manager in 2005 alongside Ben Cherington, has about as good an understanding of the Boston market as there is.
But he also understands well how Breslow operates.
When Breslow’s circuitous 17-year pitching career ended in 2018 with the Toronto Blue Jays’ Triple-A affiliate, Epstein, the Cubs president of baseball operations at the time, recruited Breslow to an entry-level front-office role auditing the Cubs’ pitching infrastructure.
As a player, Breslow was widely known as one of the smartest and most analytically minded athletes, one who first played for Epstein’s Red Sox in 2006. He quickly rose through the Cubs front office, becoming an assistant general manager in 2021. After Epstein left, the team promoted Hoyer to the top role, and Breslow was a key part of Chicago’s decision-making until he was hired by Boston in November 2023. Epstein, now a part-owner in Fenway Sports Group, has served as a mentor for Breslow over the last two years.
As Hoyer worked alongside Breslow in Chicago, he could tell it wouldn’t be long before Breslow acquired enough experience to run his own team.
“I always had a sense we were renting him because it was obvious he was going to get this opportunity really quickly, just given the number of people on this planet who have his skill set and pitched in the big leagues for 12 years,” Hoyer said.
In his first season in Boston, Breslow hired an outside auditing firm to evaluate the front office and get a better feel for how the organization operated. It was a contentious time for many longtime employees but a process he felt necessary to streamline baseball operations.
“Year 1 is such an evaluative period,” Hoyer said. “I talked to Craig so many times about that last year, where you’ve got to get in there and learn what’s going on and sort of take it all in and figure it all out. You want to make change quickly, but you also realize that it takes time. And the last thing you want to do is make bad decisions because you were hasty. I think as you get into Year 2 and beyond, it starts to become your organization.”
The trade deadline last year didn’t go as Breslow hoped, adding three pitchers — James Paxton, Lucas Sims and Luis García — who were all quickly injured as the big-league club faded down the stretch. Breslow lamented not being as aggressive as he should have been in his first year fully in charge of a club.
He learned from that deadline with an aggressive move over the winter, trading the team’s two most recent first-round draft picks in addition to two other prospects for Crochet on the final day of the Winter Meetings. Six months later, he pulled off the Devers bombshell, acknowledging mistakes in communication with Devers along the way.
Breslow has been far from perfect. He’s in only his second season leading a baseball team. Though Breslow was criticized by many for the trade, one former colleague has been impressed with what he has done so far.
“I learned a lot from him. Hopefully, he learned a lot from us,” Hoyer said. “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.”
Read more on The New York Times
