Home Baseball Chances for top 2025-26 free agents to re-sign with former teams

Chances for top 2025-26 free agents to re-sign with former teams

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Each of those six hitters played for a big-market team that could have the spending power — and need — to retain him. At the same time, there figures to be significant competition for each player’s services on the open market.

So who stands the best chance of staying put, and who is more likely to head elsewhere? To get a better idea, we asked MLB.com’s beat writers for those six clubs to weigh in on the various factors at play. Here are their responses.

Why he could re-sign: Tucker genuinely seemed to enjoy his first season with the Cubs, speaking highly of the atmosphere created behind the scenes by the veterans on a team that should be in contention for multiple seasons. And simply put, when Tucker was healthy and in the lineup, Chicago’s offense was one of the best all-around units in baseball. The Cubs have a very workmanlike approach as a group, and that also fit Tucker’s low-key personality. If the market does not generate the kind of offer the star outfielder is seeking, he knows what he has in Chicago, and it was a good thing with a solid future outlook.

Why he might not: The Cubs might not be willing to offer the kind of years that Tucker would likely hope to find on the free-agent market. Chicago has some young outfielders ready for the Majors, and it might not want to create a long-term logjam. That could turn Tucker’s attention to teams willing to invest in him over more years. As a native of Florida, Tucker might also be more comfortable with a team that has its Spring Training base closer to his home. His stint with the Cubs was Tucker’s first time training in Arizona, and when an injury issue struck late in the year, he flew to Tampa to consult his own home-based medical team.

Why he could re-sign: There was a solid fit between the Red Sox and Bregman in 2025, both on and off the field. Not only did Bregman improve the team’s production and infield defense, but he made it a point to nurture the team’s talented young core. There didn’t seem to be a day when Bregman didn’t have his iPad out giving instructive advice to a teammate about an improvement that could be made from a recent at-bat. Bregman was like an extra coach as well as a key player. The only downside of the season was that Bregman suffered a severe right quad injury in May that cost him seven weeks. Even then, he remained an active teammate and a force in the clubhouse.

Why he might not: What Bregman wants, heading into his age-32 season, is long-term security. Last season, the Sox offered the three-year contract with opt-outs after the first two years. If the club doesn’t change its stance, that will likely prevent Bregman from committing to Boston on a short-term deal with a high average annual value. Otherwise, why did he opt out in the first place? Bregman, who has only played for playoff teams during his career, would like to keep that streak going. So his priority will be to find a team that should be a sustainable winner (the Red Sox seem to fit that mold) while also being willing to offer him five years or more (unclear if Boston will do that). Why might the Red Sox face more competition for Bregman’s services than they did a year ago? It is simple. He no longer has a qualifying offer attached to him.

Why he could re-sign: Schwarber is not only one of the game’s most dangerous sluggers, but he’s the heart and soul of the Phillies — one of the best leaders Philadelphia’s clubhouse has ever seen. He’s also a valued member of the community, regularly hosting charity events in the Delaware Valley. Simply put, Schwarber has been a tremendous fit in Philly, and he would love to finish business by bringing the franchise and city a World Series championship. The Phillies know all these things, of course, and they’ve made it clear they want him back. They have the financial wherewithal to make it happen, too.

Why he might not: Other teams see what the Phillies see: a powerful hitter who has improved every season he has been in Philadelphia. Schwarber might be turning 33 in March, but he has one of the game’s best swings with elite bat speed. It’s a good reason to believe he will maintain his productivity into his late 30s. Hey, David Ortiz produced into his late 30s. Why can’t Schwarber? Sure, he’s a DH, but any team that wants power and leadership (and has the money) could outbid the Phillies for his services.

Why he could re-sign: Bichette has said all along that he wants to stay in Toronto. He wants to remain with the organization that drafted him in 2016 and developed him into an All-Star. He wants to play alongside Vladimir Guerrero Jr., his longtime friend and co-star. Sentimentality only gets you so far, but the Blue Jays clearly hold some level of a “tiebreaker” here with Bichette if everything else is even. This organization needs another big bat in the middle of the lineup, too, and who better than Bichette, whose three-run home run off Shohei Ohtani in Game 7 of the World Series was nearly an era-defining moment? The interest here is mutual and the player fits a clear need, making this a sensible reunion on all fronts, even when you put emotion to the side.

Why he might not: Bichette’s market will have a wide gap between its ceiling and its floor. Some clubs will view Bichette as a second baseman and point to his declining baserunning and athleticism. Other clubs will accept that his offensive upside is enough to cover up some defensive shortcomings and still consider him a shortstop. The Blue Jays have said publicly that they’re open to Bichette playing short, but it’s clear that Andrés Giménez could be a Gold Glover at that position if Bichette plays second. Money matters, and while Toronto could hold a tiebreaker in a tight bidding war, that sentimentality isn’t going to be enough to make up for any significant financial gap once his market finally flourishes.

Why he could re-sign: Bellinger seemed to blend into the Yankees’ clubhouse almost immediately. Teammates remarked that it felt like he had been there for years, and his pinstriped pedigree through his father, Clay, only deepened that familiarity. Beyond comfort, Bellinger delivered traits the roster badly needed. His athleticism changed the outfield dynamic, and his intelligence on the bases gave New York an element of pressure it often lacked. He can play all three outfield positions or first base, and his left-handed power fits perfectly in Yankee Stadium. Brian Cashman has already labeled him one of the two best outfielders on the market, which signals the organization sees real value in keeping him. If ownership decides to invest, the Yankees already know Bellinger’s skill set enhances the lineup, the defense and the style of play. It is easy to envision both sides agreeing that staying in New York is the best outcome.

Why he might not: Bellinger has already proven he can thrive in major markets. He succeeded in Los Angeles, rebuilt himself in Chicago and blended seamlessly into New York. That track record creates confidence for any team pursuing him. The Yankees say they have limits, and if a club steps up with more years or greater financial commitment, it would not be a surprise to see him move on. Scott Boras rarely moves quickly, and this negotiation has all the signs of one that stretches into December while multiple teams jockey for position. The Yankees also have needs in other areas, and they figure to have plenty of competition for a player with left-handed pop and a plus defender who can handle center field. It might take the highest bid to bring Bellinger back.

Why he could re-sign: Who better to fit the Mets’ Pete Alonso-sized hole than Alonso himself? In addition to being the best pure slugger among free-agent first basemen, Alonso is a fan favorite who has continually expressed his affinity for New York. He’s a lifetime Met who wants to be back. No potential replacement would represent quite the same level of slugging threat at the plate. What’s more, last offseason’s tepid league-wide interest in Alonso suggests he might never find the long-term deal he’s seeking on the open market. If the Mets can re-sign Alonso on a four- or five-year contract rather than a six- or seven-year deal, they won’t have the same concerns about the contract ending poorly. Given all that, there’s no obvious reason why this marriage shouldn’t continue.

Why he might not: Last offseason, president of baseball operations David Stearns and owner Steve Cohen proved they could stomach playing hardball with Alonso. This offseason, their Brandon Nimmo trade demonstrated a continued willingness to kick sentimentality to the curb. The Nimmo deal also made Alonso slightly less of a priority, since the Mets can now replace his bat at a corner outfield spot if they don’t do so at first base. Stearns’ top priority is improving New York’s run prevention, which also makes Alonso an imperfect fit, as he has always been a defensively challenged first baseman. And because Alonso doesn’t have a qualifying offer attached to him this offseason, he should find at least a few more suitors than he had a year ago.

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