Getty
Sonny Gray is a Boston Red Sox
Over the course of the offseason, the Boston Red Sox have made three trades to bolster their roster heading into the 2026 season. They’ve addressed some, but not all, of their needs. The Red Sox have acquired better starting pitching and recently added a right-handed power bat. While doing so, they’ve kept all of their elite prospect talent and major pieces of their MLB Roster. As of Christmas 2025, the Red Sox are better, without taking a step backward in their future.
Between trades with the St. Louis Cardinals (twice) and the Pittsburgh Pirates, it seems the Red Sox are not resting on their laurels of 2025 and want to push in 2026. That said, what do all three trades do for the team overall going into 2026?
Red Sox Adding Sonny Gray Begins Domino Effect
GettySonny Gray is a Boston Red Sox
What started the offseason in a positive direction for the Red Sox was the trade with the Cardinals for pitcher Sonny Gray. On November 25th, the Red Sox acquired Gray for RHP Richard Fitts and LHP prospect Brandon Clarke (No. 5 prospect). While Clarke was within the top-five on the Red Sox’s prospect list, he was an arm they could part with Fitts to snag 36-year-old Gray. Gray finished 2025 with a 14-8 record in 32 starts, a 4.28 ERA, along with 201 strikeouts in 1802. innings.
Fitts is considered a back-end-of-the-rotation type player, along with Clarke, who could get there someday. When adding Gray, the Red Sox acquired a possible low-end No. 2 or a high-end No. 3 within the rotation for the 2026 season. Could the Red Sox still find a bonafied No. 2 starter? Yes, they could. If not, Gray has a solid pitch mix, along with eating up innings, to be a guy to slot in behind ace Garrett Crochet.
Even with giving up a No. 5 prospect within the system, it’s still a solid move to bolster a rotation that saw Lucas Giolito and Walker Buehlar, who didn’t fully pan out as people hoped. Now, the Red Sox have a front-end starter who can eat up innings and still bring something every fifth day on the mound. All while keeping players like Peyton Tolle and Connelly Early in the system.
Johan Oviedo Shipped Up to Boston
GettyJohan Oviedo is a Boston Red Sox
Following the trade for Gray, the Red Sox, on December 4, acquired Johan Oviedo from the Pirates. They also received catcher Adonys Guzman and LHP Tyler Samaniego. In return, they sent No. 3 prospect Jhostynxon Garcia (MLB Pipeline’s No. 85) and RHP Jesus Travieso. While it is another top-five prospect going to another team, Garcia is blocked by the logjam in Boston with Ceddanne Rafaela, Jarren Duran, Roman Anthony, and Wilyer Abreu taking up roster spots. Furthermore, with Kristian Campbell taking outfield reps in the Winter League, Garcia would be stuck with guys in front of him on the depth chart.
By adding Oviedo, the Red Sox get more rotation depth for the upcoming season. Whether he could be flipped for another trade later down the road, or end up in a No. 5 spot in the rotation, it gives the Red Sox flexibility. In 2025, Oviedo, with the Pirates, finished with a 2-1 record in nine starts, a 3.57 ERA, and 42 strikeouts in 40.1 innings. He missed all of 2024 due to Tommy John surgery but returned in 2025 for a few starts.
If Oviedo can return to his age-22 season form from 2022, where he finished with a 4-3 record, a 3.21 ERA, 54 strikeouts in 56 innings, and an ERA+ of 126, this could be a solid move for the Red Sox in 2026. Just like the Gray trade, the Red Sox were able to keep their high-end pitching talent and hitters, while acquiring players who could fit in well within the rotation. Despite Garcia being in MLB Pipeline’s Top 100, it’s a move benefiting the Red Sox in terms of pitching depth at the MLB level.
Willson Contreras is joining Gray in Boston
GettyWillson Contreras is coming to Boston
The final piece of the trio of trades was Willson Contreras from the Cardinals. Late Sunday night (Dec. 21), the Red Sox acquired Contreras from the Cardinals, along with $8 million in cash considerations. In return, they sent RHPs Hunter Dobbins, Yhoiker Fajardo (Boston’s No. 23 prospect), and Blake Aita. According to Sox Prospects, they viewed Fajardo as No. 8 on their SP60 Board, along with Aita as No. 36. Overall, it was Dobbins who was the main piece of the deal.
On the latest Fenway Rundown Podcast with Chris Cotillo and Sean McAdam, they viewed Dobbins as a low-end No. 4 or a high-end No. 5 in the rotation for the Red Sox. Furthermore, they saw Fajardo and Aita as two players who could maybe be something someday. Either way, the Red Sox addressed the right-handed power bat that they needed this offseason. While it’s not a Pete Alonso or a Kyle Schwarber, they have some thump in the lineup and an above-average defender at first base.
Contreras brings a Baseball Savant page that offers some valuable insights into what the Red Sox could see in 2026. His bat speed is in the 95th percentile, while his barrel percentage is in the 86th percentile and his hard-hit percentage is in the 83rd percentile. If the bat isn’t enough, Contreras is in the 91st percentile in defensive range and in the 76th percentile in arm strength.
All in all, the Red Sox addressed their first baseman/power bat need, along with two MLB-level starters that could fit between the No. 3 and No. 5 spots in the rotation. For Oviedo, maybe even a long relief spot in the bullpen. All the while, they only gave up a No. 3 and a No. 5 prospect in their system, without losing out on elite talent like Tolle and Early. There is still a long way to go in the offseason, either way, the Red Sox are on a path to push the needle for the 2026 season. Only time will tell what else Craig Breslow and the front office will do to address more of the roster needs.
Zach Martin Zach Martin is a sports journalist covering the MLB, mainly the Boston Red Sox, for Heavy.com. He has over four years of journalism experience, and five years of podcasting experience. He’s a credentialed Carolina Hurricanes beat writer at The Hockey Writers. Zach’s previously covered the Cleveland Guardians at Covering the Corner, along with the Guardians and the Cincinnati Reds at Fansided. Zach is originally from Ravenna, Ohio, and is now based in Lexington, SC. More about Zach Martin