Suddenly, the Milwaukee Brewers have two more left-handed options for not only their starting rotation, but their pitching staff as a whole. That came with Monday’s trade, in which the Crew shipped three infielders (led by starting third baseman Caleb Durbin) and a draft pick to the Boston Red Sox for left-handed starters Kyle Harrison and Shane Drohan, as well as infielder David Hamilton.

As spring training begins this week in Phoenix, Harrison and Drohan will be in the mix to make the Opening Day roster. But where?

Harrison was the No. 1 prospect with the San Francisco Giants in 2024, and was part of the return the Red Sox got in June 2025, in the Rafael Devers trade. Still just 24, the 2020 third-round draft choice has 42 games of big-league experience, with 37 starts. Of those, 24 came during the 2024 season, in which he had a 4.33 FIP with a 7.9% walk rate and 22.2% strikeout rate.

After getting a bit of an overhaul with the Red Sox, Harrison joins a Brewers system well-known for getting the most out of pitchers, so there could be a little more to pull out of him. Harrison will compete for a rotation spot with fellow left-hander Robert Gasser, as well as right-handers Logan Henderson, Chad Patrick and Brandon Sproat. DL Hall, another left-hander, could be battling to be a starter. A second tier of prospects includes Carlos Rodriguez and Coleman Crow, if they each survive the 40-man roster crunch that could develop in camp.

Being southpaws could lend Gasser and Harrison a leg up, as the top three of Brandon Woodruff, Quinn Priester and Jacob Misiorowski are all right-handers. Harrison also has minor-league options remaining, though. As recently as 2024, the Brewers worked without a left-handed starter for most of the season.

Drohan, on the other hand, is a 27-year-old lefty who has yet to make his big-league debut. The Red Sox drafted him in the fifth round in 2020 out of Florida State. His potential was good enough for the Chicago White Sox to select him in the Rule 5 draft following the 2023 season, but he had nerve decompression surgery in his shoulder a few months later and was returned to the Red Sox in June 2024, after recovering but without cracking the active roster.

In 2025, Drohan made 14 starts and one relief appearance, primarily at Triple-A Worcester. He posted a 2.27 ERA over 47⅔ innings in 12 Triple-A games. The Red Sox added him to the 40-man roster this offseason—one reason why he was available in the trade, as the Brewers shipped three 40-man players to the Red Sox and got three back.

While likely to be stretched out as a starter this spring, Drohan could be an option as a long reliever. That could be his best path to the roster, given his age and skill set. The Brewers currently feature a wealth of left-handers in the bullpen with Hall, Aaron Ashby, Jared Koenig, Rob Zastryzny and Ángel Zerpa. That puts Drohan on a path to Triple-A Nashville to begin the season, but a top choice to come up if one of that group gets hurt.

Unless there is another trade, whether it is to use this pitching depth to acquire a potential Durbin replacement or something else, Harrison and Drohan will be second-tier contributors to the 2026 Brewers. Harrison has five years of team control remaining, though, and Drohan has all six. Harrison can be optioned to the minors not only this year, but in another season, and Drohan has all three options left. They’re incredibly flexible pieces, given their upside. They just might have to wait a while to have an impact.