The Boston Red Sox made a flurry of moves in November and early December. While none were massive marquee additions, there were some phenomenal under-the-radar pieces brought in. One of those was outfield prospect Isaiah Jackson.
The Red Sox shipped infielder Vaughn Grissom to the Los Angeles Angels ahead of the Rule 5 Draft. They got Jackson in return, a 21-year-old selected in the eighth round of the 2025 MLB Draft out of Arizona State (the Red Sox have a fun history with that college).
Adding Jackson follows an intriguing trend for the Red Sox. They barely drafted any position players this year. However, they’ve brought in quite a few 2025 position player draftees via trade (including catchers Adonys Guzman and Luke Heyman).
You could argue that Boston doesn’t need more outfielders. There's already plenty of capable outfield talent in the minor league system, while Roman Anthony, Ceddanne Rafaela, Wilyer Abreu, Jarren Duran, Kristian Campbell and Masataka Yoshida are all in the mix in the majors. So why should fans be excited about another outfield prospect?
Profiling former Angels outfield prospect, Isiah Jackson, who came to the Red Sox in the Vaughn Grissom trade
Jackson slashed .219/.324/.344 with one double and one home run in 10 games in High-A last season. The left-handed hitter drove in four runs and scored six more. Jackson has some fun offensive potential thanks to intriguing power and a strong run tool that should lead to fun on the base paths.
However, it’s his defense that makes Jackson stand out. Last season, Boston’s minor league system boasted Nelly Taylor, Miguel Bleis, Yophery Rodriguez, Skylar King, and more in the outfield. Jackson can hold his own with anyone on that list. He’s giving the Red Sox another outfield prospect with a high floor thanks to his defense/athleticism.
Expect to see the new member of the organization start the 2026 season in High-A. There, Jackson would likely join Justin Gonzales and Rodriguez. That outfield alone should make Greenville appointment viewing all summer long (or at least until they’re promoted).
Jackson’s defense, paired with his college experience and his speed/power potential combination, could help make his stay in Greenville a relatively short one.
The Red Sox have an abundance of talent in their outfield throughout the system. There have been rumors about them unclogging the logjam in the majors for a year now, but it didn't happen this winter.
Meanwhile, Craig Breslow has shown he’s not afraid to move prospects freely. Acquiring an outfielder of Jackson’s talent for someone who clearly didn’t have a future with the franchise was a move Boston should make 10-out-of-10 times.