As Kyle Schwarber returns to Philly, Boston quietly ends the Vaughn Grissom experiment with a low-risk swap for Angels prospect Isaiah Jackson.
Tuesday’s baseball news cycle was dominated by free agent slugger Kyle Schwarber opting to re-sign with the Phillies, reportedly agreeing to terms on a five-year deal worth $150 million.
Schwarber was someone Boston fans had coveted since he left the Red Sox after a half-season on the roster in 2021, where he was one of the biggest reasons why the team went on a run to Game 6 of the ALCS against the Astros.
With his bat no longer available for Boston on the open market, they now turn their complete attention to Pete Alonso, also is reportedly slated to be meeting in person with Boston on Tuesday.
As reaction to Schwarber’s signing continued to unfold, the Red Sox wasted no time getting their name back in the headlines, as the team announced a trade that sends infielder Vaughn Grissom to the Angels in exchange for Angels prospect Isaiah Jackson.
This marks the end of an era in Boston that never got underway for Grissom.
A lesser internetsman would make some sort of joke calling this “era” an “error” instead. But not me. I’m above that.
The 24-year-old second baseman/shortstop was the centerpiece of the package being sent back to Boston in 2023 by the Braves in exchange for 2024 NL Cy Young Award winner Chris Sale.
Yes, you read that timeline correctly.
After years of battling injuries in Boston, the Red Sox gave up on the ace of their 2018 World Series-winning pitching staff, sending him to Atlanta in exchange for a player in Grissom who many believed had the upside of a player that could contribute at the major league level right away for his new team.
Sale went on to have a career resurgence in 2024, winning his first career Cy Young Award and going on to have two straight seasons for the Braves with an ERA under 2.59.
Grissom batted just .190 in 31 games for Boston in 2024, and was unable to crack the major league roster at any point during the 2025 season - a far cry from the player he was for Atlanta in his first two seasons at the major league level:
2022: .291 BA, .353 OBP, .440 SLG, .792 OPS across 156 plate appearances
2023: .280 BA, .313 OBP, .347 SLG, .659 OPS across 80 plate appearances
When the Sox made that trade on paper, they looked like the easy winners.
Less than two years later, and there’s no doubt Boston wishes they could get a do-over on this one.
…should I make the “error” joke again?
Grissom was moved to Los Angeles in exchange for an eighth-round pick out of Arizona State from earlier this year.
At 21 years old, Jackson has only appeared in 10 professional games for the Tri-City Dust Devils of Pasco, WA.
In 37 plate appearances, Jackson had an OPS of .668 and an OBP of .324. He struck out 13 times and homered just once.
MassLive’s Chris Cotillo mentioned on X that Jackson’s scouting report says he “has long had tremendous raw power,” which is obviously an organizational need for the Red Sox. With that said, a 21-year-old who has only played in 10 games for the Tr-City Dust Devils in Pasco, WA is likely not making an impact at Fenway Park any time soon.
He, like Grissom, will likely be an afterthought for Boston as the look to make a real push towards a World Series in 2026.
Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.