The Boston Red Sox enter the 2025-26 offseason in a position of relative stability — a welcome change from years past. Unlike some of their recent winters filled with uncertainty, this one doesn’t come with the expectation of losing cornerstone players or making sweeping roster overhauls. Instead, Boston’s front office, led by Chief Baseball Officer Craig Breslow, faces a more calculated challenge: fine-tuning a roster that returned to the postseason in 2025 and ensuring the team continues its upward trajectory heading into 2026.
The Red Sox aren’t projected to lose any major contributors to free agency this winter, but that doesn’t mean they’ll be standing still. A few familiar names will hit the open market, and while none represent devastating losses, their departures still create gaps that need filling. Whether those holes are addressed through internal promotions, trades, or low-cost veteran signings will depend on how aggressive the organization wants to be as it looks to capitalize on the momentum built last season.
Free agency officially opened this week, following the conclusion of the 2025 World Series. The Dodgers’ seven-game victory over the Blue Jays on Saturday night marked the official start of the offseason calendar, and by Sunday morning, MLB had released its annual list of free agents. The Red Sox appeared on that list with four players eligible to test the open market: left-handers Steven Matz and Justin Wilson, utilityman Rob Refsnyder, and right-hander Dustin May.
Each of those players represents a different kind of free-agent case — from once-promising prospects to useful depth pieces to veterans nearing the twilight of their careers. None are irreplaceable, but all have value in specific contexts, and their futures could still intersect with Boston’s depending on how the offseason unfolds.
Dustin May: The Wild Card
Among the four, Dustin May stands out as the most intriguing name. Once one of the Dodgers’ most hyped pitching prospects, May arrived in Los Angeles with a fastball that touched triple digits and a sinker that moved like a Wiffle ball. His early flashes of brilliance suggested future ace potential, but repeated injuries and inconsistencies have derailed that trajectory.
Since undergoing Tommy John surgery and later dealing with elbow setbacks, May hasn’t quite rediscovered his dominant form. The Red Sox took a calculated gamble when they brought him aboard, hoping their pitching development staff could unlock some of that dormant potential. While the results in 2025 were mixed, Boston’s front office still sees a pitcher with untapped upside — if he can stay healthy.
At 28, May still has time to reinvent himself. Whether that reinvention takes place in Boston or elsewhere remains to be seen. Teams across the league value pitchers with high velocity and past success, and May’s natural movement and spin rates remain elite by modern metrics. He could receive a one-year “prove-it” contract with performance incentives, giving him a chance to reestablish himself while minimizing risk for the signing team. For Boston, reuniting with May would make sense only if the price is right — especially with young arms like Wikelman Gonzalez and Bryan Mata pushing for bigger roles in 2026.
Rob Refsnyder: The Reliable Role Player
Rob Refsnyder may not be a headline-grabber, but his value to the Red Sox over the past few seasons has been undeniable. A consummate professional and clubhouse leader, Refsnyder filled a vital role as a right-handed bat off the bench and a capable defender across multiple positions. His ability to hit left-handed pitching — particularly in high-leverage situations — gave Boston flexibility when constructing daily lineups.
Refsnyder’s versatility extends beyond his defensive assignments. He has consistently been one of the team’s most disciplined hitters, boasting strong on-base percentages and professional at-bats that lengthen games and tire out opposing pitchers. While his age (34) and limited power ceiling make him more of a complementary piece than a starter, he represents the type of steady veteran presence that contending teams need over a long 162-game season.
Should Refsnyder depart, Boston will need to find a replacement capable of providing similar adaptability. Younger players like Ceddanne Rafaela or David Hamilton could step into expanded utility roles, but there’s always a case for keeping a battle-tested veteran around. A reunion on a short-term deal would make perfect sense — especially if Refsnyder’s market remains modest.
Steven Matz: The Veteran Southpaw
Steven Matz, once one of the most promising young arms in the New York Mets organization, has traveled a winding road to this point in his career. After multiple injuries and bouts of inconsistency, Matz has transitioned from being a full-time starter to more of a swingman or middle-relief option. His time with Boston was characterized by flashes of competence, particularly when facing left-handed hitters, but it’s clear that his days as a rotation mainstay are behind him.
Still, left-handed pitchers with starting experience always draw interest in free agency. Matz could land with a team looking for depth or a veteran mentor in the bullpen. For the Red Sox, his departure likely won’t sting too much, given their internal pitching depth and potential offseason pursuits. However, if Boston seeks a steady, affordable lefty to stabilize the back end of the bullpen, bringing Matz back on a minor-league deal with an invite to spring training isn’t out of the question.
Breslow and his staff have emphasized developing homegrown arms, but they also understand the importance of depth. Injuries are inevitable, and Matz’s experience could make him a useful insurance policy if the team strikes out on other targets.
Justin Wilson: The Familiar Journeyman
Rounding out the list is Justin Wilson, the kind of pitcher who seems to pop up in free agency almost every winter. A veteran left-handed reliever with over a decade of MLB experience, Wilson has made a career out of reliability and durability. While no longer overpowering, he knows how to attack hitters, and his familiarity with high-leverage situations makes him a low-risk addition for teams needing bullpen stability.
For Boston, Wilson’s future likely depends on how aggressively they pursue bullpen upgrades. The Red Sox bullpen was a mixed bag in 2025 — effective in stretches, but prone to inconsistency late in the season. If the front office targets bigger names to complement closer Kenley Jansen (assuming he returns), Wilson’s return may not be prioritized. But should the market dry up or the team favor internal development, re-signing a known quantity like Wilson on a one-year deal would make sense.
A Stable Core and an Open Window
The encouraging news for Red Sox fans is that, aside from those four names, the team’s core remains fully intact heading into 2026. Key contributors such as Rafael Devers, Jarren Duran, Triston Casas, and Masataka Yoshida are all under contract. The rotation, anchored by Brayan Bello and Kutter Crawford, showed encouraging growth last season, while the emergence of rookies like Marcelo Mayer and Kyle Teel added youthful energy to the mix.
The Red Sox exceeded many preseason expectations in 2025, clawing their way into the postseason and reminding the rest of the league that Fenway Park can still host October baseball. With that foundation in place, the goal this winter isn’t reinvention — it’s reinforcement.
Expect the team to explore the middle tiers of free agency rather than making splashy, headline-grabbing moves. A reliable starter to eat innings, a right-handed power bat to balance the lineup, and another late-inning reliever could all be on Breslow’s shopping list. Boston’s player development department has earned praise for its progress, but blending young talent with experienced veterans remains essential for sustained success.
The Road Ahead
The upcoming months will test the Red Sox’s ability to balance patience with ambition. Their farm system, once depleted, has been replenished, and internal options are starting to bear fruit. That gives Boston flexibility — they can afford to be selective rather than desperate in free agency.
Still, the American League East remains one of the toughest divisions in baseball. The Yankees, Blue Jays, Orioles, and Rays all boast competitive rosters and deep systems. To keep pace, Boston can’t simply run it back; they need to find incremental ways to improve. Sometimes, that means retaining undervalued veterans. Other times, it means cutting ties and trusting the next wave.
The Red Sox front office knows the stakes. A playoff return in 2025 rekindled fan enthusiasm, but expectations have risen. With a few shrewd additions — and perhaps a rebound or two from familiar faces — the team could very well find itself in the thick of contention again next fall.
In short, the Red Sox’s offseason won’t be defined by who they lose, but by how they build upon what they already have. The departures of Matz, Wilson, Refsnyder, and May may open a few roster spots, but they also create opportunities for growth and innovation. Boston doesn’t need a rebuild; it needs refinement.
If Breslow and company can thread that needle — adding the right mix of veteran savvy and youthful upside — the 2026 Red Sox could be more dangerous than ever. A few “subtle moves,” as understated as that sounds, might be all that separates a good team from a true contender in the seasons ahead.
