Free agency is rapidly approaching in Major League Baseball, and after an impressive 2025 season, Boston Red Sox fans are eagerly waiting to see what additions will be made to Manager Alex Cora’s squad. The narrative surrounding the team has completely shifted — what was once uncertainty has turned into optimism about the franchise’s future, all within just six months.
The emergence of former No. 1 MLB prospect Roman Anthony as a bona fide superstar and potential future MVP, Garrett Crochet establishing himself as the ace Boston was craving after trading Chris Sale, the elite defensive play of center fielder Ceddanne Rafaela and the dominant performances of closing pitcher Aroldis Chapman all served as massive bright spots. Together, they have ramped up the pressure on Craig Breslow and the rest of the front office, as Boston fans crave nothing more than another World Series trophy in Beantown.
The offseason will begin the day after the World Series between the Los Angeles Dodgers and Toronto Blue Jays. Anticipation is growing throughout the league over where the top names will land in free agency and where others will find new homes via trade. This article will take a closer look at some of the top free-agent targets and rumored fits for the Sox, as well as a few surprise possibilities who may find themselves playing in Boston in 2026.
Tarik Skubal
A few weeks ago, Jon Heyman reported that Tarik Skubal and the Detroit Tigers are nearly $250 million apart in their contract extension talks. With just one year remaining before free agency, speculation is growing that Detroit could consider moving the 2024 Cy Young Award winner — and probable 2025 winner.
Pairing Skubal with Crochet would give Boston the best 1–2 rotation punch in the league, and there’d be no debate about it. The only problem? The price. It’s almost impossible to imagine what kind of haul it would take to pry Skubal out of Detroit. If the conversation started with Anthony, the Red Sox should shut down all talks immediately. The Sox probably don’t have enough promising prospects to interest the Tigers, and even if they did, drawn-out negotiations with Skubal about a future contract could leave Boston in a similar position to Detroit. Making a trade like this — only to watch Skubal leave in free agency to sign with the Dodgers, Yankees or Mets — would be brutal, to say the least.
Conclusion: Keep dreaming, Red Sox fans.
Hunter Greene
The 26-year-old Cincinnati Reds ace is coming off an excellent season, yet still finds his name in trade rumors. He’d fit perfectly into the Red Sox rotation — slotting right behind Crochet — and could headline a young, controllable pitching core for years to come. Greene is under club control for the next four years at a very reasonable price, which will definitely increase his trade value.
It’s not that more teams will want Greene than Skubal — Greene is in no world a Cy Young contender, let alone a winner — but the fact that he’d be around for several years without the fear of an immediate contract extension could give his market more buzz than Skubal’s.
But again, the cost would be massive (though not Skubal-massive). Any deal that includes members of the “Big 3” — Roman Anthony, Marcelo Mayer or Kristian Campbell — should, and would, result in an immediate no from the front office.
If Cincinnati were interested in a package centered around No. 3 prospect Jhostynxon Garcia, a young arm like Peyton Tolle, and one major league starter, talks could begin. However, giving up more than three or four young pieces and emptying the farm system wouldn’t be the best use of resources when free agency will provide other starting pitching options.
Conclusion: Probably not worth what it would cost.
Joe Ryan
Joe Ryan should be a familiar name for Red Sox fans, as the team reportedly came close to landing him at the trade deadline. Ryan posted a 3.42 ERA last season and ranked ninth in the MLB with a 1.04 WHIP, leading to his first All-Star Game appearance. The proposed deal at the deadline involved either Jarren Duran or Wilyer Abreu and a top prospect — possibly Garcia — a price that, in hindsight, Boston might wish it had paid.
Given the club’s outfield depth, a similar offer this offseason would make a lot of sense. The Red Sox currently have a logjam across the outfield with Duran, Abreu, Anthony, Garcia, Masataka Yoshida and Ceddanne Rafaela all vying for playing time. It’s possible that Anthony could transition into a full-time designated hitter role or move to left field, opening right field for Abreu, who took home a Gold Glove in 2024. Meanwhile, Rafaela — a current Gold Glove nominee — appears locked in as the starting center fielder for 2025. That would leave Boston with a potential outfield of Abreu, Anthony and Rafaela, making Duran a likely trade piece.
If the Minnesota Twins remain open to discussions at a similar cost, this could be one of the more realistic trade avenues for Boston to explore in its search for quality starting pitching.
Conclusion: Highly likely the Red Sox revisit this option — and a deal could very well happen.
Pete Alonso
While the three names previously mentioned are trade candidates, Pete Alonso represents one of the top free-agent targets for Boston this offseason. The 30-year-old New York Mets first baseman recently opted out of the second year of the contract he signed back in February. A five-time National League All-Star and two-time Home Run Derby champion, Alonso would bring a much-needed power bat to a Red Sox lineup that, for the most part, went flat after Anthony’s oblique strain in early September. In the win-or-go-home Game 3 of the Wild Card Series against the New York Yankees, the Sox managed just five hits and zero runs — and were in desperate need of a strong presence at the plate. There is no doubt that the potential duo of Alonso and Anthony would give opposing pitchers something to worry about.
It doesn’t seem like newly acquired first baseman Nathaniel Lowe is a long-term solution, and before his injury, Triston Casas had massive struggles at the plate, batting just .182 over 29 games. Signing Alonso to a long-term deal would go a long way toward stabilizing Boston’s infield while adding a slugger who could make good use of Fenway Park’s Green Monster.
Conclusion: The Sox will definitely be interested, but they may hesitate to make a major splash for Alonso.
Kyle Schwarber
Kyle Schwarber remains one of the game’s top home run hitters after belting 56 homers this past season. The former Red Sox slugger had a short but memorable stint in Boston, helping lead the team to a win over the Yankees in the 2021 single-game Wild Card playoff, where he hit a 435-foot home run and eventually carried the team to the American League Championship Series.
Like Alonso, Schwarber would bring serious power to the lineup but would play exclusively as a designated hitter. There will likely be a bidding war for his services, with the Philadelphia Phillies favored to retain him. Spending what is projected at upward of $30 million per year for a designated hitter (even one who delivers a ton of home runs) doesn’t seem like a good use of free agency funds for the Sox. Nevertheless, there appears to be heavy interest from Boston's side, even if a deal would leave Yoshida — the team’s current designated hitter and left fielder — as an $18 million sunk cost.
Conclusion: A fun reunion idea, but Schwarber will probably return to the Phillies. If he doesn’t, the Sox will likely be outbid.
