The Boston Red Sox made one of the most shocking moves in baseball when they traded Rafael Devers in 2025. Fans immediately questioned the decision, especially considering Devers had long been viewed as one of the franchise’s cornerstone players. While Boston did receive several pieces in return, one of the biggest names included in the package was left-handed pitcher Kyle Harrison, a former top prospect originally developed by the San Francisco Giants. Fast forward to now, and that trade tree is beginning to look even worse for Boston.
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Boston Barely Gave Harrison a Chance
After arriving in Boston, Harrison never really got an opportunity to establish himself. Rather than giving the young left-hander a chance to develop into a rotation piece, the Red Sox shipped him out this past offseason to the Milwaukee Brewers in exchange for Caleb Durbin.
Durbin has been respectable for Boston in 2026. But “respectable” suddenly looks a lot different when compared to what Harrison is doing in Milwaukee.
Harrison Is Emerging as an All-Star Candidate
Harrison has been nothing short of outstanding. Through eight starts this season, he owns:
- 4-1 record
- 2.10 ERA
- 48 strikeouts in 38.2 innings
Those are not simply solid numbers. Those are frontline starter numbers. Among National League pitchers with at least 35 innings pitched and five starts, Harrison currently owns a top-five ERA. And if he keeps this pace up, a 2026 All-Star appearance suddenly becomes very realistic.
Milwaukee has built a reputation for getting the most out of pitchers, and Harrison is starting to look like the latest example. Whether through mechanical adjustments, development strategies, or simply putting players in better situations, the Brewers consistently seem to unlock another level from arms that other organizations move on from. Now Harrison may be becoming their newest success story.
Boston Could Be Left Asking Tough Questions
The Red Sox may still believe in Caleb Durbin’s long-term value. But if Harrison develops into a top-of-the-rotation arm, the questions are only going to get louder. Because this is not just about losing a talented player. This would mean Boston:
- Acquired a major trade asset
- Barely used him
- Traded him away
- Watched him immediately become a star elsewhere
That is a difficult sequence for any front office to explain. Kyle Harrison looks like a completely different pitcher in Milwaukee. And while it’s still early in the season, the Brewers already appear to be cashing in on a move that could become another painful trade story for Boston. If Harrison continues pitching like this, Red Sox fans may be wondering what could have been for a very long time.
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