
New York Yankees general manager Brian Cashman is expected to be busy this winter. While the Bronx Bombers are set to begin their playoff push after winning 93 games in 2026, the roster could certainly improve. Third base is a clear area for Cashman to target in the offseason. Catcher and center field are also positions to keep an eye on.
Nevertheless, the Yankees could soon have a massive hole at second base as well. Jazz Chisholm is set to become an unrestricted free agent after his one-year, $10.2 million deal ends. A continued partnership between the two-time All-Star and New York was previously considered a no-brainer. In fact, the Yankees were once predicted to give Chisholm a $300 million extension. This, however, now seems increasingly unlikely.
Bleacher Report’s Zach Buckley is now anticipating that New York will sign fellow second baseman Brandon Lowe this winter. The current Pittsburgh Pirates infielder is expected to be one of the top players at his position in free agency and is not expected to re-sign with his current club. According to the reporter, the Yankees should be able to land Lowe on a three-year contract.
This is not the first time that Buckley has linked the New York Yankees to Lowe. The writer previously claimed that Cashman will soon replace Chisholm with the Pirates star. Buckley even predicted that the second baseman could get at least $25 million per year in his next deal. If true, the Yankees will be rewarding the infielder with a $75 million contract in the coming months.
New York Yankees Will Face Heavy Competition to Sign Brandon Lowe

Assuming the New York Yankees sign Lowe, it would seemingly be an upgrade at the position. The Pirates infielder currently beats Chisholm in practically every offensive category. In fact, stolen bases are the only significant area where the Yankees star has the edge. Lowe, on the other hand, is slashing an impressive .260/.331/.493 in Pittsburgh this season.
He led all Major League Baseball second basemen in home runs, slugging, and OPS on the campaign as well. Lowe’s 5.4 WAR was also tops among players at his position in 2026. Overall, this particular figure was tied for 15th-best in all of baseball. In fact, the second baseman’s WAR was only slightly lower than other stars such as Junior Caminero, Randy Arozarena, and Elly De La Cruz.
The New York Yankees, however, will face tough competition in the Lowe sweepstakes. As Buckley points out, several MLB teams will want to sign the star in free agency. The Toronto Blue Jays have already been linked with a potential move for the infielder as well.
New York Set to Host Rivals in Postseason Clash
For now, the New York Yankees will focus on the 2026 playoffs. The club is set to host the Boston Red Sox in the wild card round. The two rivals will begin the five-game series in the Bronx on September 29. New York recently named Cam Schlittler, Max Fried, and Gerrit Cole as starting pitchers for the first three games. Immediately following the campaign, however, Cashman will look to free agency to strengthen his roster.
Yankees Predicted to Sign $75 Million Infielder to Replace Star