It would be hard to argue that the 2023 Chris Sale trade went well for the Boston Red Sox, and not just because Sale immediately won the National League pitching Triple Crown and Cy Young Award for the Atlanta Braves.
The Red Sox received middle infielder Vaughn Grissom as their return, who posted only 31 games for them in 2024 due to multiple injuries and time spent in the minor leagues. In 2025, he never saw the major leagues at all.
At the 2025 Winter Meetings, Boston flipped Grissom to finally get a usable return in the Sale trade. The Red Sox have traded Grissom to the Los Angeles Angels in exchange for minor league player, first reported by MLB insider Jeff Passan. Chris Cotillo of MassLive soon announced that the Sox got No. 25 prospect Isaiah Jackson in return.
The Grissom trade opened a spot on the Red Sox's 40-man roster, with which they can make a pickup in the December 10 Rule 5 Draft, but fans would rather hope a Winter Meetings blockbuster trade or signing will come.
Red Sox trade Vaughn Grissom to Angels for top outfield prospect, declaring an official loss on the Chris Sale trade
Grissom's fit with the Red Sox was questionable when they first acquired him, and only became worse after Marcelo Mayer and Kristian Campbell's debuts. Grissom came to Boston as a shortstop while it had Trevor Story and the then-top prospect Mayer already in the mix for future starts there. The Red Sox then turned Grissom into a second baseman, but Kristian Campbell became the starting second baseman on Opening Day, leaving him in the minor leagues.
Many reporters and fans saw this trade coming after some comments Grissom made after Mayer's season-ending injury on July 23. The infielder was passed over for a promotion, in favor of David Hamilton, after he'd performed well at the plate for a few weeks.
“It’s a weird one because I don’t really expect much more opportunity here just because decisions that were made were made, and it kind of didn’t involve me,” Grissom said to Katie Morrison-O'Day ofMassLive.
Grissom batted just .190/.246/.219 with a .465 OPS over his 31 games with Boston. He didn't fare as well as expected in the minor leagues, either, with a .259/.385/.373 slash line and .758 OPS over 55 games. In 2025, he posted an improved .270/.342/.441 and .783 OPS, and he did deserve that shot in the major leagues that was taken by Hamilton, who struggled offensively for as long as he was on the roster.
This trade gives Grissom a potential path to the big leagues while helping the Red Sox flip him for an asset they have more use for. Jackson is just 21 years old and only appeared in High-A for the Anges in 2025, so it'll be a while before the Red Sox see him in the major leagues. They could also flip him in another trade this winter.