MLB Insider: 3 Former Red Sox Executives Face Trade Deadline Pressure

Craig Breslow is feeling the heat following Sunday’s blockbuster Rafael Devers trade. But he’s not the only front office executive facing scrutiny as the MLB trade deadline approaches.

That’s according to ESPN MLB insider Buster Olney, who assembled a list of seven executives with the most at stake ahead of the July 31 deadline. Included on his list are three former members of the Red Sox front office.

Arizona Diamondbacks general manager Mike Hazen held the same title with the Red Sox in 2015 and 2016 under team president Dave Dombrowski.

“Hazen will have a lot of say about what happens at this year’s trade deadline because if Arizona decides to trade talent, he’ll dangle a highly marketable set of players,” Olney wrote Monday. That list includes Josh Naylor, Eugenio Suarez, Merrill Kelly and Zac Gallen.

But with a strong core of players, Olney also noted Arizona could look to buy rather than sell. The Diamondbacks (36-35) are in fourth place in the National League West and three games out for the final NL wild card. FanGraphs gives the Diamondbacks a 34.8% chance of making the playoffs.

Dave Dombrowski is in his fifth season as Phillies president of baseball operations. Red Sox fans will remember him as the architect of the 2018 championship team. But in Philadelphia, Dombrowski hasn’t enjoyed the same success. Yes, he assembled a roster that reached the World Series in 2022 and the National League Championship Series the following year.

“However, the Phillies’ group of position players is older, with Bryce Harper in Year 7 of the 13-year deal he signed and Kyle Schwarber and J.T. Realmuto in the last years of their respective contracts,” Olney wrote. “The team’s window is now.”

The Phillies (43-29) are in second place in the NL East, two games behind the first-place New York Mets. FanGraphs gives Philadelphia an 89% chance of reaching the playoffs.

And then there’s Jed Hoyer. Part of the Red Sox front office from 2002 to 2009, he helped build the roster that broke the “Curse of the Bambino.“

Now the president of baseball operations for the Cubs, Hoyer picked up another World Series title when Chicago snapped its title slump in 2016. And he’s hoping for another ring this year.

“Chicago is so good — its offense so dynamic and versatile, its defense so efficient — that one evaluator believes that the question for Hoyer is not whether the Cubs will make the playoffs … but what will make them more dangerous in the meaningful games they’re bound to play at the end of the season,” Olney noted.

The Cubs (44-28) sit in first place in the NL Central and have an 88.6% chance of making the playoffs according to FanGraphs.