Red Sox Make Multiple Roster Moves To Prepare For Rule 5 Draft Deadline

The Boston Red Sox made a bevy of roster moves Tuesday afternoon in the lead-up to the deadline of being able to protect players from the Rule 5 Draft. Entering the day, the Red Sox 40-man roster was full as it was expected for the team to make some room to open a spot for pitcher David Sandlin.

Instead, the team began the flurry of roster moves by trading Luis Guerrero to the Tampa Bay Rays for infielder Tristan Gray, per MassLive's Chris Cotillo. Guerrero, who had been previously designated for assignment and went unclaimed, didn’t open any roster spot but instead put the team at 41 players on the 40-man roster. The need for an opening led the Red Sox to designate Nathaniel Lowe for assignment.

The first baseman joined Boston in August after being released by the Washington Nationals. He helped to provide stability at first base after the team had relied on a combination of Abraham Toro and Romy González. Appearing in 34 games, Lowe hit .280/.370/.420 with six doubles, a triple, two home runs, and 16 RBIs. Projected to earn around $13.5 million in arbitration, Lowe was viewed as a non-tender candidate, so the announcement of being DFA’d was not much of a surprise.

The team followed the roster turnover by designating Josh Winckowski for assignment. Winckowski, the last remaining player in the system from the Andrew Benintendi trade, was viewed as another non-tender candidate due to other relievers having passed him on the depth chart. After a surprise campaign in 2023 that saw him become a trusted option in Alex Cora’s bullpen, Winckowski was never able to repeat that success as he struggled in 2024 before a flexor strain in his right elbow limited him to six games with Boston in 2025. Winckowski pitched in 121 games during his four seasons in Boston, making 21 starts. The right-hander went 13-14 with five saves and a 4.20 ERA in 242 1/3 innings pitched.

With those moves, Boston saw their 40-man roster drop to 39, leaving room to add at least one player. But the team wasn’t finished; they would move another reliever a few hours later. With 33 minutes until the deadline to protect players, the Red Sox shipped left-hander Chris Murphy to the Chicago White Sox, according to USA Today's Bob Nightengale. In return, the Red Sox received catcher Ronny Hernandez. Murphy made his debut with Boston in 2023, where the left-hander appeared in 20 games for the team. Through July, he pitched well, allowing just five earned runs across 28 1/3 innings, suggesting he could be a key bullpen piece if the team hoped to overcome injuries to its starting pitchers. Unfortunately, he fell off in August from possibly being overused, allowing 17 earned runs in 14 1/3 innings before only tossing five innings in September. Murphy would miss the 2024 season after undergoing Tommy John surgery in April of 2024. He would return in 2025, appearing in 23 games and going 3-0 with a 3.12 ERA in 34 2/3 innings. For his career, Murphy pitched in 43 games for Boston and had a 4.15 ERA in 82 1/3 innings.

Hernandez is 21 years old and spent the 2025 season with Single-A Kannapolis, where he hit .251/.344/.336 with 12 doubles, one triple, four home runs, and 34 RBIs. Hernandez signed with the White Sox at 17 in 2022, and he immediately played in the DSL, throwing out 51% of base stealers. In 2025, he appeared in 64 games behind the plate, committing 10 errors in 622 defensive chances. He also threw out 24% of base stealers, up from 14% in 2024.

Now down to 38 players on the 40-man roster, David Sandlin was added to the roster as reported by SoxProspects’ Andrew Parker. Sandlin was the one prospect everyone expected to be added to the roster, but it ended up being that he wasn’t alone. Chris Cotillo soon added that both Shane Drohan and Tyler Uberstine were also to be added, the two pitchers having previously been viewed as candidates, but it was unclear whether they would be added. Both spent most of the 2025 season in Worcester, pitching well enough to gain the attention of the front office to protect them from the Rule 5 Draft. With Worcester, Drohan appeared in 12 games, making 11 starts and going 5-1 with a 2.27 ERA in 47 2/3 innings pitched. What stuck out for him was his 67 strikeouts in that span. Uberstine made 19 appearances for Worcester, going 6-4 with a 3.56 ERA in 91 innings. He also struck out 102 batters.

With the 40-man roster back up to 41 players, the Red Sox made one more trade to bring it back down to 40 players as they shipped left-handed reliever Brennan Bernardino to Colorado for minor leaguer Braiden Ward, as first reported by Beyond the Monster’s Hunter Noll. Bernardino joined the Red Sox back in 2023 after the team claimed him off waivers from Seattle, and he immediately became one of Cora’s most-used relievers during his tenure with the team. In three seasons with Boston, Bernardino appeared in 169 games, making 12 starts as an opener and going 10-8 with a 3.47 ERA across 155 2/3 innings. During that time, he struck out 157 batters and walked 68 while allowing just 11 home runs.

Ward, who plays center field, left field, and second base, split last season between Double-A and Triple-A, where he hit a combined .290/.395/.391 with 17 doubles, four triples, two home runs, and 37 RBIs in 97 games. Most of Ward’s playing time in 2025 came in the outfield, playing 78 of his 97 games between left field and center field. He did play six games at second base and three at third base. Center field appears to be his best position defensively, as he’s made just four errors there in 456 defensive chances in his career.

Boston finished the day by trading pitcher Alex Hoppe to the Seattle Mariners for catcher Luke Heyman, per Tim Healey of the Boston Globe. Hoppe, who was drafted by the Red Sox in 2022, split 2025 between Portland and Worcester, appearing in 44 games. The right-hander tossed 61 1/3 innings, striking out 73 batters and walking 34. He also had a 4.55 ERA. Hoppe was best known for his fastball, which could reach triple digits, and his slider, which, when he was on, could make batters look silly. Hoppe appeared in 123 games with the Boston organization, tossing 176 innings and striking out 203 batters.

Heyman was Seattle’s 14th-round pick in this year’s draft, having played three years of college baseball for the University of Florida. In 2025, Heyman played in 49 games, hitting .301/.397/.578 with seven doubles, one triple, 13 home runs, and 44 RBIs. He did not play in any professional games after being drafted.

Craig Breslow had a busy Tuesday as he overhauled the backend of the 40-man roster while adding prospects into the system. The offseason has only been in session for a few weeks, but Breslow seems willing to make moves, and it should make for an interesting offseason.