As the dust settles on the Boston Red Sox’s 2025 campaign, the mood in New England is a cocktail of hope, frustration, and eager anticipation. The season, which saw Fenway Park come alive with youthful energy and dramatic moments, ended abruptly with a Wild Card exit at the hands of the New York Yankees. Now, with the offseason officially underway, attention turns to the front office’s next moves—and the futures of a handful of key veterans whose contracts are up for grabs.
The Red Sox entered the 2025 season with high expectations, buoyed by a promising start and the emergence of young stars. Fans were treated to electric nights at Fenway, such as Payton Tolle’s mesmerizing debut, Wilyer Abreu’s inside-the-park homer followed by a grand slam, and Ceddanne Rafaela’s walk-off heroics. The clinching of a playoff berth was a moment of pure elation, a sign that Boston baseball was back in the spotlight. As one fan reflected, “The energy was incredible, the excitement was real, and the world was our oyster for that moment and for a few days after.”
But the postseason script flipped quickly. The Red Sox, hampered by a rash of injuries and a roster stretched thin, bowed out early. The Yankees, bolstered by their own deadline reinforcements, proved too much for a Boston squad missing key contributors like Rob Refsnyder, Wilyer Abreu, and Roman Anthony. Injuries to pitchers Walker Buehler, Richard Fitts, Jordan Hicks, Brennan Bernardino, and Lucas Giolito further depleted the staff, forcing manager Alex Cora to lean on inexperienced arms like Connelly Early and Payton Tolle in the season’s most crucial moments.
General manager Craig Breslow didn’t mince words in his postseason remarks. “We’re sitting here in October not having accomplished what we set out to accomplish, so I think it would be irresponsible not to go back and think about all of the decisions that were made leading up to today,” Breslow admitted. He acknowledged the limitations of the trade deadline moves, which netted only two rental pitchers, Dustin May and Steven Matz, instead of the impact arms fans hoped for. “We went into the deadline with a few goals, and it kind of became apparent that some of those weren’t going to be able to be achieved and pivoted. Sometimes those work out. Sometimes they don’t.”
Indeed, the trade deadline will be dissected for months to come. Boston shipped power-hitting prospect Blaze Jordan to St. Louis for Matz and dealt James Tibbs III and Zach Ehrhard to Los Angeles for May, who had fallen out of favor in the Dodgers’ rotation. Matz delivered a 2.08 ERA over 21 2/3 innings, but his underlying numbers—a 4.84 FIP and 4.20 xERA—suggested some good fortune. He was reliable as a middle-innings lefty, but not the solution against right-handed bats that Boston sorely lacked.
May’s stint was, by all accounts, a disappointment. In just 28 1/3 innings, he posted a 5.40 ERA and a 5.39 FIP, with the Red Sox losing five of the six games he pitched. Elbow neuritis sidelined him for the final month and the Wild Card Series. As one fan put it, “It feels unfair to say Dustin May because he didn’t choose to be put into this situation but nevertheless his time was torturous.” The Red Sox have shown a recent tendency to sign injured pitchers to multi-year deals, but with May’s inconsistency and health woes, any return would likely be on a low-risk contract.
Justin Wilson, the 38-year-old lefty, brought value to the bullpen with a 3.35 ERA and 27.5% strikeout rate in nearly 50 innings. He excelled against left-handed hitters (.212/.292/.282 slash line allowed) but was less effective versus righties. With only so much room for veteran left-handers, his future in Boston may hinge on his willingness to accept another short-term, low-cost deal—and his belief in the Red Sox’s 2026 championship potential.
Rob Refsnyder, a fan favorite and versatile bench piece, continued to thrive in his role. He hit .269/.354/.484 overall, but his numbers against lefties were eye-popping: .302/.399/.560 with a 159 wRC+. However, Refsnyder missed 12 games late in the season due to injury, and at 35 years old (come Opening Day 2026), retirement or a move to another team remains on the table. With Romy Gonzalez waiting in the wings, the Red Sox may face a tough decision on whether to offer Refsnyder a raise over his $2.1 million 2025 salary or let him walk.
One silver lining for Breslow and his staff: the payroll is getting a significant reset. Over $32 million in dead money—owed to Eric Hosmer, Walker Buehler, Abraham Toro, and Michael Fulmer—comes off the books, giving Boston more financial flexibility to address roster needs. That’s real cash that could be used to re-sign one or more of their own free agents or pursue outside upgrades.
Looking back, the 2025 season will be remembered as a turning point. The arrival of Roman Anthony, the emergence of Payton Tolle, and the resurgence of Trevor Story gave fans hope that a new core is forming. As one observer noted, “This will be remembered as not necessarily a new dynasty, but a new core—and hopefully one that’ll stick around for longer than two years after winning a World Series.”
Yet, the shortcomings of the trade deadline, the painful injuries, and the thin roster in October were hard lessons. Alex Cora, reflecting on the season’s end, said, “The roster that we had at the end wasn’t the roster we had early in the season or during the season. So it’s actually very hard for me to compare.” The front office’s gamble on depth and health didn’t pay off when it mattered most. Other playoff contenders, like the Mariners and Blue Jays, prioritized depth and reaped the rewards down the stretch.
As the Red Sox head into the 2025-26 offseason, all eyes are on Breslow and the front office. The decisions they make on Matz, May, Wilson, and Refsnyder will shape the team’s immediate future. Will Boston double down on veteran experience, or will they clear the way for a new generation to take the reins? One thing’s for sure: with payroll flexibility and a core of rising stars, the Red Sox are poised for a pivotal winter.
For fans still stinging from the early playoff exit, there’s solace in knowing that the 2025 season rekindled excitement at Fenway and set the stage for what could be a thrilling new era. The next few months will reveal whether Boston’s brass can turn that promise into postseason glory.