THE BILL COMES DUE
Part 1: What Craig Breslow Has Actually Done to the Boston Red Sox
Craig Breslow took over as Boston's Chief Baseball Officer on October 25, 2023, inheriting a franchise that had finished last in the AL East in back-to-back seasons. His mandate was clear: fix the pitching, compete sooner rather than later, and do not dismantle the organizational foundation beneath him.
Two years later, Boston made the postseason for the first time since 2021. The narrative wrote itself. Visionary executive transforms a broken franchise. The reality is more complicated, and it starts with an honest accounting of what Breslow actually walked into.
The Foundation He Inherited
When Baseball America ranked Boston's farm system No. 1 in baseball entering 2025, the praise was warranted. What often goes unsaid is who built it.
The players who drove Boston's early Breslow-era production were almost entirely developed or acquired before he arrived. Jarren Duran, a fixture in the Boston lineup since 2021, posted 8.7 bWAR in 2024 on a near-minimum salary, production worth roughly $78M on the open market, paid at just above the league minimum. Brayan Bello, Tanner Houck, Kutter Crawford, Ceddanne Rafaela, and Triston Casas were all Chaim Bloom-era draft picks or acquisitions. Even the much-praised 2023 draft class was assembled under Bloom's watch. Breslow deserves credit for managing the roster he inherited. He does not deserve credit for building most of the young core that carried it.
That class includes fourth-round pick Kristian Campbell. He made the Opening Day roster in 2025, got off to one of the more electric starts of any Red Sox rookie in recent memory, and was handed an 8-year, $60M extension just five games into his career. Five games. The scouting report was apparently "trust us." Campbell then hit .223 across 67 games before being optioned back to Triple-A, where he spent the rest of 2025 and opened 2026. Whether that extension pays off remains to be seen. The credit for drafting him belongs to Bloom regardless.
That is not a minor distinction. He inherited a legitimate foundation. What he did on top of it is the actual question.
The Free Agent Record
Breslow's stated mission was to fix the pitching. He spent aggressively across two offseasons. If the goal was to fix the rotation, he accidentally assembled the baseball equivalent of a warranty claim department.
Lucas Giolito: 2 years, $38.5M. Missed all of 2024 with a UCL injury. Returned in 2025 for a serviceable but unspectacular season. Total cost: $37M. Total WAR: 2.5. That is $14.8M per win above replacement against a market rate of roughly $9M.
Liam Hendriks: 2 years, $10M. Delivered 13.2 total innings across both seasons before elbow surgery ended his Boston tenure. Walker Buehler: $21M, 5.45 ERA, released in August. Patrick Sandoval: 2 years, $18.25M, missed all of 2025 with Tommy John surgery.
Four pitching free agents. Two offseasons. Roughly $68M spent. Combined WAR delivered: approximately 3. At market rate that money should have produced nearly 8 wins above replacement. The gap between expected and actual return is roughly 5 wins. His mission was to fix the pitching. The free agent record shows he has not.
The One Move That Holds Up
In November 2024, Breslow traded catcher Kyle Teel (14th overall in 2023, the consensus best catching prospect in baseball), outfielder Braden Montgomery (12th overall in 2024), infielder Chase Meidroth, and pitcher Wikelman Gonzalez to the Chicago White Sox for left-hander Garrett Crochet. Effectively two first-round picks plus depth. The return was undeniable.
Crochet went 18-5 with a 2.59 ERA, led the AL with 255 strikeouts, finished second in Cy Young voting, and signed a 6-year, $170M extension. On his arb salary of $3.8M he delivered 6.0 WAR, roughly $630,000 per win. The signature move of the tenure.
On the same afternoon, Breslow quietly acquired catcher Carlos Narvaez from the Yankees for minor pieces. Narvaez posted 2.5 WAR in 2025, hit .273, and ranked top-3 among AL catchers in fielding run value. Two moves, one day, zero meaningful cost. Both belong in Breslow's credit column.
Payton Tolle, Breslow's second-round pick in the 2024 draft, debuted in 2025 and carries genuine rotation upside, the first top-50 pick used on a pitcher since Tanner Houck in 2017. A real organizational win.
The Decision That Changed Everything
In February 2025, Breslow signed third baseman Alex Bregman to a 3-year, $120M deal. It addressed a legitimate right-handed power void. The problem was convincing Rafael Devers he was no longer the third baseman.
Devers, locked in at third base under an 11-year, $331M deal and the unquestioned face of the franchise, was told he would be moving to designated hitter. He arrived at spring training visibly unhappy. The friction was real and never recovered.
Then in June 2025, with Devers hitting .272/.401/.504 with 15 home runs in the middle of a playoff race, Breslow traded him to San Francisco. The return: Kyle Harrison, Jordan Hicks, James Tibbs III, and minor league arm Jose Bello. Within months, Hicks had a -1.0 WAR and the organization had to attach No. 8 prospect David Sandlin just to move his contract. Tibbs was traded to the Dodgers. Harrison was the one meaningful piece, and what Breslow did with him is the subject of Part 2.
The Bregman signing created the Devers problem. The Devers trade produced almost nothing. And Bregman, after one solid season, signed with the Cubs on a 5-year, $140M deal. Boston created organizational friction for a one-year rental and traded their franchise cornerstone in the process. Baseball's most expensive Airbnb stay.
One Playoff Run, and Who Earned It
Boston finished 89-73, made the Wild Card, beat the Yankees in Game 1, and lost the series. First October since 2021. The city celebrated. Breslow took a bow.
But the rotation he constructed had Buehler released mid-season and Sandoval never throwing a pitch. The offense ran on players Bloom developed. Crochet was elite. Around him, manager Alex Cora navigated a flawed roster better than it deserved, as he had throughout his career. Cora's .534 winning percentage across his Red Sox tenure speaks for itself.
Breslow extended Cora through 2027 at $7.25M annually in the summer of 2024. That confidence would last exactly 27 games into the following season.
Boston entered 2026 with Crochet, Ranger Suarez on a 5-year, $130M deal, Sonny Gray, and Johan Oviedo. A franchise cornerstone traded away. A manager locked up through 2027. In February, Sam Kennedy stood in Fort Myers and said what ownership believed.
"There's no ceiling on the 2026 Boston Red Sox. This group, if things come together and we have good health, I think sky's the limit."
It did not come together. Part 2 explains why, and who is responsible.