When The Athletic released its top 50 free agents for the 2025–26 offseason, the White Sox were linked as potential fits for five of them. While a few names—such as Gleyber Torres and Jorge Polanco—felt like odd fits, one player on the list stands out as an ideal addition for the 2026 roster.
The team’s most pressing needs remain at the corner infield spots, in the bullpen, and possibly in the outfield, depending on whether the club decides to retain Luis Robert Jr. and Mike Tauchman.
Outfielder Trent Grisham is the first player on Jim Bowden’s list who makes genuine sense for Chicago. The 29-year-old is coming off a breakout season with the Yankees, hitting a career-high 34 home runs and posting a personal-best 3.5 WAR.
His left-handed power would play perfectly at Guaranteed Rate Field, and he could serve as a right-field upgrade over Tauchman in a platoon role until top prospect Braden Montgomery is ready for the majors.
A two-time Gold Glove winner in center field, Grisham has also seen limited action in the corner outfield positions, logging fewer than 20 games each in left and right. While he doesn’t hit for average, his disciplined approach at the plate aligns with the organization’s growing focus on patience and on-base ability. He owns a career 12% walk rate and drew 82 walks last season.
Grisham also brings with him postseason experience, appearing in 26 playoff games during his time with the Brewers, Padres, and Yankees.
Even if the White Sox retain both Robert Jr. and Tauchman, they’ll still feel the loss of veteran leader Michael A. Taylor, who retired at the end of the season. Taylor appeared in 134 games for the White Sox, the third most of any player on the team. If the White Sox were to pick up Robert Jr’s option and flip him at the deadline, Grisham could shift into center field.
Bowden projects Grisham to command a two-year, $30 million deal—well within the team’s financial reach.
