The Chicago White Sox once saw the upside in Shane Drohan, but his delayed breakout is a reminder that identifying talent is only half the battle in the Rule 5 Draft.
The success of Shane Smith and Mike Vasil in 2025 introduced a fair number of Chicago White Sox fans to the Rule 5 Draft and the opportunity it brings every year.
The Rule 5 Draft was created to prevent teams from hoarding talent in the minor leagues without giving deserving players an opportunity to make the 40-man roster or reach the big leagues. Players signed at age 18 or younger are given five seasons in an organization before they must be added to the 40-man roster. If a player is older and signed out of college, that window shrinks to four seasons.
If a player is left off the 40-man roster after that period, they become eligible to be selected in the Rule 5 Draft. Once selected, they are immediately placed on their new team’s 40-man roster and must remain on the active MLB roster for the entire season. Otherwise, they are waived and offered back to their original team.
We’ve already seen this play out for the White Sox this season with right-handed pitchers Jedixson Paez and Alexander Alberto. Chicago selected both players in the Rule 5 Draft. Alberto was returned to the Tampa Bay Rays during spring training, while Paez initially stuck on the active roster. But less than a week into the regular season, Paez was designated for assignment after it became clear he wasn’t ready for the challenges of Major League Baseball. He’s now back in the Boston Red Sox minor league system.
That might feel like a failure on the surface, and I’ve certainly been critical of how the White Sox have handled their 40-man roster with this group, but in reality, the vast majority of Rule 5 picks end up being returned to their original teams. Shane Smith and Mike Vasil are the exceptions, not the rule. And even before their success, the White Sox regularly took shots in the Rule 5 Draft that didn’t stick.
In December 2022, the White Sox selected right-handed pitcher Nick Avila in the Rule 5 Draft. He was coming off a dominant season with a 1.14 ERA across 47 minor league relief appearances. After a rough spring training, Avila didn’t make the team and went on to post a 14-0 record with a 3.00 ERA in Triple-A for the San Francisco Giants the following season.
A year later, in December 2023, the White Sox selected left-handed pitcher Shane Drohan from the Boston Red Sox. Drohan landed on the 60-day injured list before the season even began, which initially looked like a path to keeping him in the organization long term, since injured list stints still count toward the Rule 5 roster requirement.
But once Drohan began a rehab assignment, he looked nothing like himself. Walks became a major issue, and by June, he was designated for assignment and returned to Boston. Now, two seasons later, Drohan is finally starting to show the potential the White Sox once saw in him. After a strong 2025 season, he was called up earlier this week by the Milwaukee Brewers to make his MLB debut.
Drohan was traded from Boston to Milwaukee in a six-player deal centered around Caleb Durbin heading to the Red Sox. That trade was finalized in February after Drohan had been added to Boston’s 40-man roster in November.
In a fitting full-circle moment, Drohan made his MLB debut against the Red Sox while wearing a Brewers uniform on Wednesday. He got the start, threw 2.2 innings, and allowed three runs.
Who knows how long Drohan will stick in the big leagues or if he’ll ultimately develop into a reliable MLB pitcher. But at just 27 years old, the potential is still there. And his journey is a reminder of how difficult it is to get the Rule 5 Draft right.
The White Sox correctly identified Drohan’s talent back in December 2023, but identifying tools and getting the timeline right are two very different things. Chicago may have been early, and now it could be Milwaukee that ultimately benefits if Drohan turns into a valuable piece.
In fact, with Drohan’s debut, every White Sox Rule 5 Draft pick since 2000 has now appeared in a Major League game at some point in their career. The only exception is Alberto, who was selected in this past year’s draft.
Nick Avila (2022) reached the big leagues with the San Francisco Giants in 2024. Jordan Romano, selected in December 2018, went on to become an All-Star closer and is now with the Los Angeles Angels. Outfielder Carlos Tocci, taken in 2017, appeared with the Texas Rangers in 2018.
White Sox fans will also remember Dylan Covey, who made 45 starts for the team before later appearing with Boston, Philadelphia, and the Los Angeles Dodgers. In 2013, the White Sox selected catcher Adrian Nieto, who played 48 games the following season. A year earlier, they selected infielder Angel Sanchez, who appeared in just one game for Chicago despite prior big league experience.
And back in 2003, the White Sox selected right-handed pitcher Jason Grilli, who went on to enjoy a long MLB career that lasted until 2017, including an All-Star appearance with the Pittsburgh Pirates in 2013.
The Rule 5 Draft isn’t just about identifying players who can eventually become big leaguers. It’s about finding players who are ready for the challenge right now while still having room to develop.
Shane Drohan is just the latest example of the White Sox getting only half of that equation right.