DARK SECRETS: Craig breslow | Rare Historical Photos

The Seven Biggest Upgrades of the 2026 MLB Trade Deadline

From sorely-needed starting pitchers to coveted catchers, here are the seven biggest upgrades of the 2026 trade deadline.

Sports Illustrated · Aug 4

The Red Sox Got Better and Still Lost the Trade Deadline

The Boston Red Sox made some improvements at the 2026 MLB trade deadline, but chief baseball officer Craig Breslow vastly overpaid in every deal he made.

Sports Illustrated · Aug 4

Five Winners and Five Losers From the 2026 MLB Trade Deadline

Baseball’s trade action picked up in a big way ahead of Monday’s deadline. Here’s how the dust settled.

Sports Illustrated · Aug 4

Trevor Story, Red Sox Players Rip Front Office for Firing Alex Cora, Coaches

Craig Breslow addressed the players in the clubhouse before Sunday’s series finale—and it did not go well.

Sports Illustrated · Apr 26

Alex Cora’s Firing Is the Final Straw. John Henry Should Sell the Red Sox

After the original sin of the Mookie Betts trade in 2020, Boston’s owner has overseen a number of missteps that have left the franchise in disarray.

Sports Illustrated · Apr 26

How Red Sox Felt About Losing Alex Bregman to Cubs in Free Agency

The Red Sox were “disappointed” after Bregman agreed to a contract with the Cubs.

Sports Illustrated · Jan 13

Craig Breslow Had Odd Line After Red Sox's Quiet Trade Deadline

As competitors built up their rosters, the Red Sox were quiet at the deadline.

Sports Illustrated · Aug 1, 2025

Red Sox Fans Chant 'Keep Duran' at Top Front Office Executive Amid Trade Speculation

The Fenway faithful made it clear to Craig Breslow that they want their outfield to remain in tact.

Sports Illustrated · Jul 11, 2025

Orioles Player Had Funny Message for Red Sox Exec After Rafael Devers Trade

One Orioles player was especially grateful that Craig Breslow and the Red Sox traded Rafael Devers to the Giants.

Sports Illustrated · Jun 17, 2025

Red Sox Exec Craig Breslow’s Bold Line After Rafael Devers Trade Led to Lots of Jokes

Many compared the Red Sox exec to Dallas Mavericks GM Nico Harrison.

Sports Illustrated · Jun 17, 2025