New York Yankees starting pitcher Carlos Rodon (55) pitches against the Toronto Blue Jays (Image via Imagn). The New York Yankees could be preparing for one of the biggest offseason moves in baseball, as reports suggest they are expected to target two-time World Series champion and three-time All-Star Alex Bregman. The veteran infielder, who spent the 2025 season with the Boston Red Sox, appears set to enter free agency once again – a decision that could send ripples across the American League East.Bregman’s possible arrival in New York would undoubtedly strengthen the New York Yankees’ lineup but also complicate their infield situation. With Ryan McMahon already holding down third base, the move would raise questions about defensive alignment and long-term roster balance. Yet, for a franchise always in pursuit of championships, adding a player of Bregman’s caliber may be too tempting to resist.
Alex Bregman’s Free Agency and Contract Outlook
Alex Bregman is fully expected to opt out of his deal with Boston this winter. His decision doesn’t completely rule out a Red Sox return, but it does position him as one of the most coveted names in the free agent class for the second straight offseason.
Boston Red Sox base runner Nate Eaton (right) celebrates with Alex Bregman after scoring in the ninth inning (Image via Imagn)
At this stage of his career, Bregman is likely chasing his final major contract, one that could approach or exceed $182 million. Analysts have compared his potential market value to Matt Chapman’s previous six-year, $151 million extension following a rebound year with the San Francisco Giants. Given Bregman’s consistency, leadership, and championship pedigree, he’s widely expected to secure a contract of equal or greater value.
Why the New York Yankees Make Sense
Bregman’s reputation as a winning player and leader makes him an ideal fit for a team with championship aspirations. He’s known not only for his offensive production but also for mentoring younger teammates and performing under postseason pressure. Those attributes align perfectly with the New York Yankees’ long-standing focus on experience and mental toughness.As one insider put it, Alex Bregman “was a leader in the Boston clubhouse by example and words, mentoring many of the Red Sox young future stars. He will be sought-after in free agency as the industry views him as a winning player who can contribute on both sides of the ball and perform on the biggest stage in the biggest moments. He’ll likely seek a long-term contract instead of settling for a shorter-term deal like he did last year.” (H/t: Sporting News)
Infield Complications Loom for New York
If Bregman lands in the Bronx, the New York Yankees will face tough decisions regarding lineup structure. Ryan McMahon currently occupies third base, leaving Bregman to either compete for the position or shift to left field to maintain his everyday role.PositionCurrent PlayerPotential Adjustment 1B Anthony Rizzo No change expected 2B Gleyber Torres Possible trade candidate 3B Ryan McMahon May share or rotate duties SS Anthony Volpe Remains starter LF Vacant Likely spot for Bregman
A Defining Offseason for the New York Yankees
Signing Alex Bregman would instantly elevate the New York Yankees’ offense and clubhouse presence but could also disrupt their current balance. His addition might push other roster moves or defensive realignments, signaling a significant strategic shift in how the team approaches 2026.Also read: MLB trade rumors: New York Mets predicted to land $65 million Atlanta Braves DH to bolster squad amid Pete Alonso uncertaintyAs Hunter Cookston noted, bringing in Alex Bregman “would make for an intriguing offseason in New York – one full of questions about fit, positioning, and long-term direction.” Whether the Yankees take that gamble could determine the franchise’s path for years to come.