Red Sox shuffle roster with four trades, DFA Nathaniel Lowe and Josh Winckowski, add three pitching prospects to 40-man

It was a busy day for Red Sox chief baseball officer Craig Breslow.

The Red Sox made four trades on Tuesday afternoon to clear spots on the 40-man roster. Boston traded hard-throwing right-handed reliever Luis Guerrero to the Rays for infielder Tristan Gray. They also sent left-handed reliever Chris Murphy to the White Sox for minor league catcher Ronny Hernandez, according to USA Today’s Bob Nightengale.

The Sox traded dependable left-handed reliever Brennan Bernardino to the Rockies for minor league utility man Braiden Ward. The three minor league positional players acquired today in the three separate trades are a reversal from the past few off-seasons, where Breslow focused on the pitching pipeline.

The fourth trade for the Sox in a flurry of moves landed them minor league power-hitting catcher Luke Heyman from the Mariners for right-hander Alex Hoppe, according to The Boston Globe’s Tim Healy.

A LOOK AT THE DEALS

Gray, 29, appeared in 30 games for the Rays last season, where he batted .231/.282/.410 with three homers, five doubles, and a .410 slugging percentage in 86 plate appearances. He’s spent time with the Athletics and Marlins, playing in 47 major league games since 2023. Gray has played all infield positions, spending most of his time at shortstop in the minors.

The Pirates initially drafted the versatile infielder, who played collegiate ball at Rice, in the 13th round of the 2017 MLB Draft. Gray was never considered a top prospect in baseball but has had back-to-back 30-homer seasons in 2022 and 2023 with the Rays’ Triple-A affiliate, the Durham Bulls.

Boston has a handful of middle infielders on its 40-man roster that offer additional positional versatility in David Hamilton, Nate Eaton, and Nick Sogard. If all four are still with the organization by spring training, they will compete for a spot on the Red Sox 26-man Opening Day roster.

The Red Sox recently designated Guerrero for assignment and outrighted him to Triple-A Worcester, sending him to Tampa Bay. Over the last two seasons in Boston, the hard-throwing righty recorded a 2.63 ERA, allowing eight runs in 27 1/3 innings in 22 games. Guerrero has struggled with his command, allowing 16 walks over that span. If Guerrero had remained in the Sox’ organization, he would have provided bullpen depth for the WooSox and could have been one of the first relievers recalled if Boston needed an additional arm for the bullpen.

While at the general manager meetings in Las Vegas last week, Breslow praised Guerrero to reporters.

“It’s tough because we’ve spent so much time building out (his) stuff and appreciating the impact that raw stuff can have on a bullpen,” Breslow said. “I still think that Guerrero has plenty of upside and plenty of outs to get.

“He worked incredibly hard to get himself to this point to become a big leaguer, and there’s a ton of raw stuff. Great arm... When you get to a place where you are needing to DFA guys that you think have real stuff and the ability to get outs in the big leagues, I think it speaks to the depth that the organization has been able to amass.”

Murphy, 27, returned from Tommy John surgery this season and pitched well out of the Sox’ bullpen, recording a 3.12 ERA with 30 strikeouts in 34 2/3 innings of work. The southpaw made 43 appearances for the Red Sox, split between 2023 and 2025, all of them coming in relief.

Hernandez, 21, played in 82 games for the White Sox' Single-A affiliate last season, where he slashed .251/.344/.336/.679 with four homers. The move adds more catcher depth within Boston’s system, which lacks viable minor league catching options.

In addition to Hernandez, the Sox are also adding Heyman, a power-hitting catcher who was drafted in the 14th round last year by the Seattle Mariners out of Florida. He offers raw power but struggles with off-speed pitches at the collegiate level.

“While Heyman struggled somewhat with offspeed pitches, particularly changeups, he crushed velocity, a byproduct of solid bat speed and rhythm,” Baseball America wrote about Heyman. “He stays balanced through his swing and can punish mistakes over the plate… Scouts believe he has a chance to stick behind the plate thanks to above-average arm strength and improved receiving and blocking. He presented pitches more cleanly than in years past and showed a feel for handling a staff.”

Heyman belted 41 homers in three seasons while at Florida and has not yet made his professional debut.

Hoppe, 26, finished the 2025 season with the Triple-A Worcester Red Sox after also spending part of the season with Double-A Portland. In 37 appearances with Worcester, he went 0-2 with a 4.76 ERA with 24 walks and 56 strikeouts. The Mariners added the righty to the 40-man roster.

Bernardino has been a workhorse for Alex Cora out of the bullpen the last handful of years, posting a 3.14 ERA over 51.2 innings and 55 appearances in 2025.

Ward, 26, plays both infield and outfield and saw time at Triple-A this past season, batting .331 with a .906 OPS in 44 games. He’ll provide positional player depth at the upper levels of the system for next season.

ROSTER CRUNCH

With the deadline looming to protect players on the 40-man roster, Boston also designated first baseman Nathaniel Lowe for assignment to make room for Gray.

Lowe, 30, appeared in 34 games for the Red Sox after signing a big league deal with the club following his release from the Nationals.

The Sox also designated right-handed pitcher Josh Winckowski for assignment. Both Winckowski and Lowe were arbitration-eligible this offseason. Lowe was expected to earn a raise from his $10.4 million salary from last season. He was projected to earn $13.5 million in the second year of the arbitration process. He could come back to Boston on a lower salary if the club opts to go in another direction and keep him at first base for next season.

Boston is reportedly focusing on upgrading at first base this winter, and securing Lowe at $13.5 million seems like a significant investment for a player who just finished a season where he hit .228 with 18 home runs, 84 RBI, and a .689 OPS in 153 games, split between Washington and Washington.

Winckowski, 28, only logged 11 2/3 innings last season, splitting time with Boston and Worcester before he was placed on the 60-day injured list with a flexor strain in his right elbow. While with the Sox, Winckowski was used primarily as a swingman, appearing in 242 1/3 innings and making 21 starts. If the Sox had kept him on the 40-man roster, the righty would have been arbitration eligible and was projected to earn $800K next season.

Boston still has the option to trade both Lowe and Winckowski after they are designated for assignment. Winckowski has three years of control remaining and could be an intriguing controllable pitching option for a club adding depth.

The Red Sox also added right-handed minor league pitchers David Sandlin and Tyler Uberstine and left-hander Shane Drohan to the 40-man roster, protecting them from the Rule 5 draft in December.

Sandlin is another hard-throwing right-hander in the Sox’ system, who posted a 3.97 ERA in 14 starts between Double-A Portland and Triple-A Worcester, recording 71 strikeouts in 70 1/3 innings.

This past summer, the Red Sox converted Sandlin into a reliever to give the big league club another option for the bullpen down the stretch. Sandlin struggled pitching out of the bullpen, finishing the year posting a 4.50 ERA with 107 strikeouts in 106 innings split between Double-A and Triple-A.

Drohan, 26, was eligible for the Rule 5 draft again and had a productive year back in the Red Sox’ system. He posted a 2.27 ERA with 67 strikeouts in 47.2 innings over 12 outings (11 starts) with the WooSox. The White Sox had previously selected Drohan in the 2023 Rule 5 Draft, but they later returned him to the Red Sox. He was limited to just 16 1/3 innings due to a series of shoulder injuries in 2024.

Uberstine did not pitch in 2023 due to Tommy John surgery and tossed just 4 2/3 frames in 2024. The 26-year-old had a big year between the Sea Dogs and WooSox, tossing 120 2/3 innings in 25 outings (21 starts) while recording a 3.58 ERA with 137 strikeouts.

The Rule 5 draft is held in December, and it provides clubs around the league the opportunity to select minor leaguers who might be blocked from getting to the 40-man roster. Boston has had success the last few years dipping their toes into the Rule 5 Draft, selecting Garrett Whitlock and Justin Slaten.

AROUND THE LEAGUE

Four players accepted the qualifying offers from their respective teams, a new league record. The Brewers right-hander Brandon Woodruff, the Yankees outfielder Trent Grisham, the Cubs right-hander Shota Imanaga, and the Tigers second baseman Gleyber Torres will all return to their teams on one-year, $22.025 million deals.

Based off the way the offseason has been moving along, it would have been a lock that Red Sox starter Lucas Giolito would have accepted the qualifying offer had the club extended it to him.

NOTABLE DFA’S

The following players were designated for assignment:

1B Michael Toglia (Rockies)

OF JJ Bleday (Athletics)

IF/OF Christopher Morel (Rays)

SP Frankie Montas (Mets)