On June 25, the 32-46 Boston Red Sox were safely categorized as trade deadline sellers. Three weeks and 13 wins later, they're now just as safely considered deadline buyers.
Back when Boston was having fire sale conversations, Sonny Gray was its most obvious trade candidate. The veteran's outstanding season had him linked to a fair few teams in the playoff race.
One team that needs to be discussed a lot more is the Chicago Cubs. The reason we should discuss the Cubs more is simple: I think the Red Sox could get the best package back from Chicago.
The Cubs are desperate. They have had issues with their pitching staff all year and just lost Edward Cabrera to a pretty gnarly hamstring injury. Ben Brown went down with a neck injury as well. Cade Horton and Justin Steele are on the 60-day injured list and Jameson Taillon is on a rehab assignment. That’s a legitimate playoff starting five on the IL — the Cubs are begging for pitching.
Gray has looked better and better as the season goes on. Sure, he’s on the older side, and he’s not an ace. The Cubs are more starved for pitching, though. They’re also a bit more desperate to stay in the playoff race because the National League Central is so competitive this year. For many reasons, Chicago may be more inclined to give up the farm.
A realistic trade deadline return package for Red Sox's Sonny Gray if Boston was still selling
If Gray was up for grabs, the package would ideally start with Josiah Hartshorn. The 19-year-old has burst onto the scene in High-A and is now a top-100 prospect according to MLB (and No. 2 in Chicago’s system).Â
Hartshorn is slashing .276/.395/.498 with 15 doubles, three triples, and 15 home runs between Single-A and High-A. The switch-hitting outfielder/first baseman has driven in 69 runs, scored 59, and stolen nine bases in 82 games between the two levels.
Hartshorn was a sixth-round pick out of High School in 2025 and doesn’t turn 20 until February of 2027. He’s a young, fast-rising prospect at a position of need (first base) for the Red Sox.
However, the Sox probably could've gotten a lot more because of how utterly dominant Gray has been. Throw in someone like right-handed pitcher JP Wheat (unranked. He’s not having a great year in High-A (8.85 ERA in 20.1 innings), but the 23-year-old is 6’5” and can flirt with 100 with nasty movement. The Red Sox would probably love to try to get him on the right path.
Then go to the ACL and grab Fernando Cruz (No. 27 prospect in the system). Cruz is a 19-year-old right-handed-hitting shortstop with fantastic speed and intriguing pop who’s already shown impressive fielding ability for his age.
The trade return doesn't feel the most exciting when you consider the closest player to the majors is a 19-year-old with under 30 games in High-A. However, Chicago would've made the trade because it wants to win now. The Cubs wouldn't give the Red Sox a player who’s ready to help at Fenway in 2026 or even likely in 2027.
Thankfully, the Red Sox have improved so much that their thoughts of selling are just a memory. Gray and his 2.48 ERA and 12 wins get to stay in Boston for a playoff run closer to home.
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