Both the Boston Red Sox and New York Yankees enter 2026 with well-positioned rosters capable of making a run, but each faces the challenge of addressing two high-profile free agents.

Outfielder Cody Bellinger and infielder Alex Bregman are both in need of new deals or replacements. Both are represented by agent Scott Boras as they look to secure contracts this offseason.

Each is coming off a strong year. Bellinger posted a .272 batting average, a .334 on-base percentage, an .813 OPS, 29 home runs and 98 RBIs across 152 games while providing elite defense in the outfield for the Yankees.

Bregman, in his 2025 season with Boston, recorded a .273 batting average, .360 on-base percentage, .821 OPS, 18 home runs and 62 RBIs in 114 games.

Both Bellinger and Bregman joined their respective teams in 2025, and with free agency now underway, last season could prove to be their only year in pinstripes or with the Red Sox.

As Bregman and Bellinger enter the offseason, their focus has shifted toward staying healthy and sharpening their skills for 2026.

Neither player is on an active roster, yet both have made it clear they are committed to maintaining peak condition while navigating free agency. In recent weeks, the two stars have been spotted training in Arizona, appearing to work out together or at least at the same facility.

Their offseason program has been highlighted by sessions with Nemesis Baseball, a sports performance community that promotes itself on Instagram as “Sports Performance community for those who seek to reach their full potential / Built By Athletes For Athletes.”

Bregman and Bellinger recently shared photos of their workouts, giving fans a glimpse into the intensity of their preparation.

The posts quickly drew attention, not only for the training itself but also for the interaction between the two free agents. Bregman responded to Bellinger’s post with a simple message, “Dialed 💪.”

This interaction comes after a report from Mark Feinsand of MLB.com predicting Bellinger’s next team. According to Feinsand, “New York is the clear favorite to sign Bellinger.” While the Yankees appear positioned to retain their star outfielder, Bregman’s future is less certain.

The Red Sox have expressed interest in bringing him back, but they have not yet been identified as clear front-runners, leaving open the possibility that Boston could lose its veteran infielder after just one season.

Over the course of their careers, both players have built impressive track records that place them among the most decorated stars of their era.

Bregman has been named to three All-Star teams, won two World Series titles with the Houston Astros, collected a Gold Glove and a Silver Slugger and earned All-Star Game MVP honors. Bellinger’s accolades include National League MVP, Rookie of the Year, two All-Star selections, a Gold Glove, two Silver Sluggers and a World Series championship with the Dodgers in 2020.

His best years came in Los Angeles, while Bregman’s peak was with the Astros. Both were key figures in the 2017 sign-stealing scandal, yet that chapter appears behind them, as they now train together and show genuine camaraderie.