The Boston Red Sox are at a crossroads as the 2025 Major League Baseball season nears its end. With a roster brimming with young talent, the team has the luxury of making bold decisions this offseason. While players like Jarren Duran, Ceddanne Rafaela, and Wilyer Abreu have solidified their places in Boston’s future, not everyone is guaranteed a spot. The Red Sox front office, led by manager Alex Cora, faces tough choices about which veterans to retain and which to let walk in free agency. According to a recent analysis by ClutchPoints, three players—Dustin May, Rob Refsnyder, and an unnamed third player—stand out as potential candidates to depart. This article explores why these players might not fit into Boston’s long-term plans and how their exits could pave the way for a new era at Fenway Park.
The Red Sox have undergone a transformation in 2025, driven by an influx of young talent. Prospects like Roman Anthony, Marcelo Mayer, and Kristian Campbell have made significant impacts at the major league level, delivering on the hype surrounding their arrivals. On the pitching side, Hunter Dobbins and Payton Tolle have emerged as potential anchors for the rotation, giving Boston a foundation to build around. This youth movement has shifted the team’s focus toward long-term development, making veterans with expiring contracts less critical to the roster.
The emergence of these young stars has given the Red Sox flexibility. As ClutchPoints notes, “The Boston Red Sox have a roster full of young talent, giving them the freedom to let some of their veterans move on this winter.” This strategic pivot allows the front office to prioritize cost-effective, high-upside players over aging or inconsistent contributors. With the team fighting for a playoff spot in the American League, the decisions made this offseason could define Boston’s trajectory for years to come.
Dustin May: A Trade Deadline Gamble That Didn’t Pay Off
One of the most notable names on the potential departure list is pitcher Dustin May. Acquired at the July 31 trade deadline, May was seen as a high-upside addition to bolster Boston’s pitching staff. However, his tenure with the Red Sox has been underwhelming. As ClutchPoints reports, “May has no place in the team’s long-term development plans.” His performance since joining Boston has not matched the promise he showed earlier in his career with the Los Angeles Dodgers, where injuries and inconsistency plagued his development.
May’s struggles are not entirely surprising. After undergoing Tommy John surgery in 2022, his second such procedure, May has struggled to regain the form that once made him a top prospect. His brief stint with Boston in 2025 did little to change that narrative. With young pitchers like Dobbins and Tolle stepping up, the Red Sox have less need for a reclamation project like May. Letting him walk in free agency could free up resources to pursue more reliable pitching options, such as a veteran starter or a high-leverage reliever.
Rob Refsnyder: A Veteran Outfielder Overshadowed by Youth
Outfielder Rob Refsnyder is another player who may not return to Boston in 2026. At 34 years old, Refsnyder has been a serviceable role player for the Red Sox, but his playing time has dwindled in 2025. As ClutchPoints points out, “Refsnyder has played in 59 games this season. He is on pace to play the second-fewest games in a single season of his time with the Red Sox.” With the outfield now a strength for Boston, thanks to the emergence of Anthony, Rafaela, and Abreu, Refsnyder’s role has become expendable.
Refsnyder’s versatility and veteran presence have been valuable, but the Red Sox outfield is poised for a new era. The trio of Anthony, Rafaela, and Abreu brings a dynamic mix of speed, defense, and offensive potential that evokes memories of Boston’s iconic outfields of the past, such as the Mookie Betts, Jackie Bradley Jr., and Andrew Benintendi group. ClutchPoints notes, “Based on their production at the plate and the field, the group is reminiscent of past teams. If they can match Mookie Betts, Jackie Bradley Jr., and Andrew Benintendi, Boston doesn’t need Refsnyder.” His departure would allow the Red Sox to fully commit to their young core, potentially saving salary cap space for other needs, such as bolstering the bullpen.
While ClutchPoints explicitly names May and Refsnyder as players the Red Sox could let walk, the third player remains unspecified in the analysis. This ambiguity adds an element of intrigue to Boston’s offseason plans. Could it be a high-profile veteran like Alex Bregman, who is rumored to be a free agency target for multiple teams? Or perhaps a lesser-known reliever like Jordan Hicks, whose 2025 season was marred by a shoulder injury? The uncertainty surrounding this third player fuels speculation among Red Sox fans, who are eager to see how the front office navigates the free agency market.
One possibility is that the third player could be a bullpen arm like Kenley Jansen, who, according to NBC Sports Boston, has already shown signs of wanting to move on. Jansen’s decision to leave early at the end of the 2024 season sparked controversy among teammates, and his high salary may not align with Boston’s focus on cost-effective roster construction. As John Tomase of NBC Sports Boston writes, “Whatever slim chance Jansen had of re-upping went out the window when the All-Star closer flew home a couple of days early, much to the consternation of some offended teammates.” Letting Jansen walk could allow the Red Sox to invest in younger, more affordable relievers like Tanner Scott or Devin Williams, as suggested by ClutchPoints.
The decision to let players like May, Refsnyder, and potentially a third veteran walk reflects a broader strategy for the Red Sox. With a strong core of young players and a pitching staff that has become a strength, the team is well-positioned to compete in the American League. The addition of Garrett Crochet, described by ClutchPoints as “one of Boston’s best additions in recent memory,” further bolsters the rotation. If Cora can find complementary pieces to support Crochet, the Red Sox could emerge as a legitimate contender in 2026.
However, these moves are not without risk. Letting go of veterans like Refsnyder or a high-profile free agent like Jansen could impact team chemistry and leadership. Alex Cora, who has guided the Red Sox through a transitional 2025 season, remains optimistic about the team’s direction. In a recent statement, Cora emphasized the importance of young talent, saying, “Players like Dustin May, Rob Refsnyder, and Jarren Duran have a chance to play spoilers if they make it into the American League postseason.” While Cora’s comments highlight the potential of these players, they also underscore the reality that not all will fit into Boston’s long-term vision.
For Red Sox fans, the upcoming offseason is a chance to see the team’s future take shape. The emergence of prospects like Anthony, Mayer, and Tolle has injected excitement into the fanbase, but the decisions to let veterans walk will test the front office’s ability to balance youth and experience. The potential departure of players like May and Refsnyder could signal a shift toward a more dynamic, homegrown roster, but it also raises questions about how Boston will address gaps in the bullpen and lineup.
The intrigue surrounding the unnamed third player adds a layer of curiosity. Will the Red Sox make a splash by letting a big name like Bregman or Jansen walk in favor of younger talent? Or will they surprise fans by retaining a veteran to mentor their rising stars? As the offseason unfolds, these questions will dominate discussions in Boston and beyond.
The Boston Red Sox are on the cusp of a new era, one defined by a talented young core and a pitching staff with immense potential. Letting players like Dustin May and Rob Refsnyder walk in free agency could be the first step toward building a roster capable of contending for a World Series. While the third player remains a mystery, the decisions made this winter will shape the Red Sox’s trajectory for years to come. With Alex Cora at the helm and a fanbase hungry for success, Boston is poised to make waves in the free agency market. Stay tuned to see how the Red Sox navigate this pivotal offseason and whether their bold choices pay off in 2026.
