The Boston Red Sox deployed 23 different position players during the 2025 season, yet Vaughn Grissom never saw Fenway Park. Acquired two offseasons ago in the blockbuster swap for nine-time All-Star Chris Sale, the 24-year-old infielder spent the entire year at Triple-A Worcester while Boston cycled through second-base options at the major-league level. At this point, it seems nothing Grissom does will restore him to the organization’s plans.
With the offseason underway, the Red Sox and Grissom are headed for a clean break. A team insider confirmed to MassLive’s Chris Cotillo that the partnership is all but over heading into 2026.
“Vaughn Grissom remains on the 40-man roster but is one of the more clear change-of-scenery candidates in baseball after not cracking the big league roster once in 2025,” Cotillo wrote Thursday.
Grissom’s .190 average in 31 games during 2024 makes a significant trade return unlikely, but Boston still has paths to extract some value. The preferred route: move him quickly in a deal—however minor—before the roster deadline forces exposure to waivers. Even a low-level lottery ticket could yield upside; the alternative is losing him for nothing.
Consider the precedent set last winter. The Red Sox flipped minor-league reliever Chase Shugart to Pittsburgh for pitching prospect Matt McShane, a former 13th-rounder who posted a 2.55 ERA in 2025 and earned a rapid promotion to High-A. Shugart was days away from being DFA’d; McShane became a useful organizational piece.
If no trade materializes before the Rule 5 Draft in early December, Boston will almost certainly designate Grissom for assignment to protect a more promising prospect. The clock is ticking on a once-promising marriage that never took root.