The World Series 2025 winners have not been crowned yet, but the off-season talks have started in full swing. And sure, there are several players in the spotlight, but one among them whom no one can talk about is Kyle Schwarber. His journey with the Philadelphia Phillies has been nothing but remarkable. He had signed a four-year $79 million deal before the 2022 season, and what good has he done for the team? He went from being a streaky power hitter to one of the most prolific home run sluggers in baseball.

Over the life of that contract, he blasted 187 home runs and trailed only Judge and Shohei Ohtani in this feat. Not everyone can achieve this feat—and now at 33 years old, he is testing the free agency again after having a career year in the National League with 56 home runs and 132 RBIs and getting his third all-star selection. Now, as a DH, his value comes exclusively from the plate, but it would be wrong to discount the “veteran” value he brings to teams.

For the Phillies, retaining Schwarber seems to be the most logical move. In theory, Nick Castellanos could move to the DH spot, but that would leave a void in the outfield, which would force them to try for Kyle Tucker or probably Cody Bellinger. So, from a production value and leadership standpoint, the Phillies may find Schwarber too important to walk away. However, nothing is written in stone, and last off-season’s Juan Soto x New York should be enough to tell one. So if he doesn’t make it to Philadelphia, here are four more spots he could land.

Chicago Cubs

The Chicago Cubs could be the sentimental favorite for Kyle Schwarber. Given that Kyle Tucker could potentially head to the Los Angeles Dodgers, Chicago could have an opening in both the outfield and the DH slots. Their top prospects, like Owen Caissie and Kevin Alcantara, could compete for the starting right field job, or Seiya Suzuki could slide back to that spot. This would leave the DH spot open for someone like Moises Ballesteros or maybe Schwarber.

Jon Heyman even mentioned the nostalgia factor, saying, “Cubs—now, that’s a little nostalgic for me. I’d love to see him back with the Cubs. That was a beautiful marriage.” Schwarber was honestly a fan favorite during his first stint there, and yes, a reunion can excite the fan base. Still, Chicago’s off-season focus is seemingly on pitching, but if they want to have an edge, then bringing in a power bat could be a game-changer. The only kicker is the finances, making it tricky.

Chicago’s offseason focus is expected to be pitching, especially in the starting rotation. But if they want to maintain their competitive edge, bringing in a proven power bat like Schwarber could be a game-changer—even if finances make the move tricky. For many Cubs fans, seeing “another Kyle” back in Wrigley is an enticing proposition.

Boston Red Sox

Boston Red Sox fans still talk about the time when they decided to let Kyle Schwarber walk away in 2021, and it still stings them. He, after all, had played a key role in their extremely unexpected ALCS run, and then he ended up signing with the Phillies. However, the real matter is that the DH spot in Boston in recent years has been a weak link. The team ranked 15th in home runs last season, which is a far cry from the league’s other powerhouses, be it the Yankees, Dodgers, etc.

Bringing Schwarber could fix plenty of issues, adding right-handed pop, amping up the lineup, and giving that veteran presence in the clubhouse. Also, the Boston Red Sox can atone for the past missteps by offering him a role where he can dominate. Sure, the team has options, but a reunion does seem interesting and in the realm of possibility.

Toronto Blue Jays

The Toronto Blue Jays are another team to watch out for, more so because of their connection to Ranger Suarez. So he is expected to test free agency this winter, and the Jays are seen as the landing spot. Their rotation already has Kevin Gausman, Jose Berrios, and Chris Bassitt, but a dependable left-handed starter is missing. Adding Suarez could give them balance, and adding Schwarber could help bolster the Jays’ lineup as a power DH.

Schwarber’s impact on the Jays would not be limited to the home runs; he would be the voice guiding his team and ensuring they make a great run. The Blue Jays are right now in a strong financial position to make a competitive offer, and pairing Schwarber with the existing roster could be a great choice for the team needing both offense and leadership.

San Francisco Giants

Finally, the Giants could be in the mix. With Buster Posey taking the reins and building the team for 2026, the team is trying to position itself to be more relevant than it has been in years. He may not provide much defensively, but his bat and clubhouse presence could help accelerate the development of a young and talented roster.

Heyman mentioned, “Number five, a team with money and likes to spend is the Giants. They need to add offense still. Obviously, they got the big left-handed bat in Devers. Maybe add one more.” A competitive offer from the Giants could tempt Schwarber even if he ultimately prefers the Phillies. This is because the opportunity to shape a contending team could be too enticing to give up, even for Kyle Schwarber.

For now, sure, the Phillies are a practical spot, and they did make him an offer in spring training. But if the Cubs, Red Sox, or anyone makes a good offer, then he may be headed elsewhere.