The Boston Red Sox made another trade this week, returning to a familiar partner (something they seem to be doing lately). This time it was the Milwaukee Brewers.
Milwaukee sent infielder Caleb Durbin, utility players Andruw Monasterio and Anthony Seigler, and a competitive balance pick to Boston. In return, the Red Sox shipped off infielder David Hamilton and pitchers Kyle Harrison and Shane Drohan.
Drohan was the most inconspicuous player of the three in Milwaukee's return package. Hamilton had a breakout year in 2024, but became a scapegoat for many fans in 2025 due to his struggles on offense. Meanwhile, Harrison was possibly the biggest part of the Rafael Devers return (after his departure, prospect Jose Bello is the only part of Boston's return still in the organization).
Drohan is just another pitching prospect in a loaded system, though. At least that’s how some fans may view him.
What the Red Sox lost in Shane Drohan, part of the Brewers' return in Caleb Durbin-Kyle Harrison trade
The Red Sox have incredible pitching depth, and they used some of that depth to get needed help in the infield. However, that doesn’t mean it doesn’t sting to lose Drohan.
The left-handed pitcher enjoyed a dominant start to the 2023 season in Double-A that put him on many people’s radar, but Drohan struggled following a promotion to Triple-A. A dip in velocity was one of the more worrying issues.
In the 2023-24 offseason, Drohan was selected by the Chicago White Sox in the Rule 5 Draft. Injuries derailed his season, and after making just 10 appearances (9 1/3 innings) in Chicago’s minor league system, he was returned to the Red Sox.
Drohan looked like that early 2023 season version of himself last season. The lefty posted a 2.27 ERA, .185 BAA, and 1.01 WHIP over 12 appearances (11 starts) with Worcester. He struck out 67 batters compared to 16 walks in 47 2/3 innings.
Importantly, Drohan’s velocity was up, and he was able to maintain that velocity deeper into games and deeper into the season. That meant his fastball was consistently around 94 MPH (even going up over 96 MPH). With good command of the pitch, adding velocity was huge. Especially considering how well it complements his top-tier changeup.
You could look at the 27-year-old and say it’s not a big loss considering he’s yet to make his Major League debut. That could be attributed to some bad luck, the Rule 5 Draft, and injuries, though.
Drohan was an intriguing option even with his flaws in 2023. In 2025, he limited walks, punched guys out at a big rate, added velocity, and produced deeper into games. Another jump in 2026 is certainly not out of the question.
The Red Sox already have plenty of pitching, and in an ideal world, wouldn’t have needed to use Drohan in 2026. But it’s very possible there’s a point in the season where Boston could use a pitcher, and fans are looking longingly at the Brewers while Drohan is dealing (we saw it with Quinn Priester, even though that was a good trade by the Red Sox).
Boston fans just need to hope that Durbin and Co. can produce well enough that any potential Drohan dicing doesn’t hurt too much.