Craig Breslow's Best (And Worst) Trade of 2026 for the Red Sox

When the Boston Red Sox were preparing for the 2026 Major League Baseball season, they clearly viewed the trade market as a significant way to bolster the roster ahead of the campaign.

Last offseason, it was a talking point around the team that Boston was utilizing the trade market far more than free agency, at least initially. Over the last few years, Red Sox chief baseball officer Craig Breslow has shown over and over again that he's not afraid to swing a big deal. If you look at the 2026 roster, it was full of guys acquired by way of the trade. Now that the season is over, the time is now to look back and break down the best (and worst) deal by the organization.

Best Deal: Acquiring Willson Contreras From The St. Louis Cardinals

Sep 29, 2026; Bronx, New York, USA; Boston Red Sox first baseman Willson Contreras (40) is introduced before game one of the Wildcard round for the 2026 MLB Playoffs against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | IMAGN IMAGES via Reuters Connect

First base was a black hole for the Red Sox over the last few years ahead of the 2026 season. That's because of some unfortunate injuries to slugger Triston Casas. The 26-year-old has played in 92 games since 2024. As injuries popped up, Boston had to figure out the position on the fly. Last offseason, the Red Sox made a change and targeted Contreras instead, and the move was a great one.

Boston sent Hunter Dobbins and pitching prospects Yhoiker Fajardo and Blake Aita to the Cardinals in exchange for Contreras and cash to pay down his deal. Contreras responded with one of the very best seasons of his career. He slashed .275/.386/.516 with a .901 OPS, 27 home runs and 81 RBIs in 130 games played. Contreras set a new career high with his 27 long balls and was a leader for the organization all year.

Plus, to make matters better, Contreras is under contract for the 2027 season and has a $20 million club option for the 2028 season as well. Boston traded three players away who likely wouldn't have played much of a role in 2026 and got a star.

Worst Deal: Acquiring Johan Oviedo From The Pittsburgh Pirates

Mar 2, 2026; Dunedin, Florida, USA; Boston Red Sox starting pitcher Johan Oviedo (29) throws a pitch during the first inning against the Toronto Blue Jays at TD Ballpark. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

Unfortunately, every deal wasn't a winner, at least initially. Boston traded outfield prospect Jhostynxon Garcia and right-handed pitcher Jesus Travieso to the Pirates in exchange for Oviedo. The righty flamethrower only was able to pitch in one game in the majors in 2026. He's under team control for the 2027 season, but will be a free agent afterward. Fortunately, Boston has one more season with Oviedo, but the 2026 campaign was a wash.

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