The White Sox had a significant improvement from 2024-2025, as they won 19 more games this past season. This was solid progress, as they looked like a much more competent baseball team. This improvement was due to a lot of factors, but most importantly, contributions from their top prospects.
This sets the White Sox up for continued improvement throughout the organization in 2026, as they will have another top draft pick and room to add players from outside the organization. Despite the White Sox being one step closer to contention, they should not stop adding low-risk, high-reward players, as it is likely they won’t be in the hunt for the playoffs this season. These acquisitions could come in the form of former top-100 prospects who haven’t gotten much playing time with their current organization or have bounced around a few teams.
There has already been one move like that this offseason, as the White Sox acquired former top-100 prospect Everson Pereira from the Tampa Bay Rays. This is a high-upside move, as the White Sox could tap into the talent that made Pereira a top-100 prospect and into a valuable middle of the order bat.
When looking at the free agent market, there are a few players that stand out as potential fits for the White Sox this season. One of those players is former Los Angeles Dodger and Boston Red Sox starting pitcher, Dustin May.
May has had a very interesting major league career to this point. Prior to making his debut, he was a consensus top prospect across most baseball media outlets. May did not disappoint, as in 2019, when he made his major league debut, he threw 34 innings of 3.63 ERA baseball.
After 2019, May had a very good shortened 2020 season, as he came in 5th place in the Rookie of the Year voting. He posted a 2.57 ERA over 56 innings, with a very good 1.089 WHIP and 44 strikeouts to just 16 walks. This was a great start to his MLB career, as you couldn’t have asked for much more.
Unfortunately for May, the injury bug has hit him hard. Prior to the 2025 campaign, he has not thrown more than 48 innings in a season, while completely missing the 2024 season. This has been a tough break for May, but he stayed mostly healthy in 2025.
After missing a significant amount of time, it was expected that 2025 would be a bit rougher than most of his other seasons. May was able to throw 104 innings with the Dodgers prior to the trade deadline, pitching to a 4.85 ERA with a 1.3 WHIP. He struck out 97 batters while walking 46. The Dodgers then traded him to the Red Sox at the deadline.
Dustin May tonight
6 IP
1 ER
3 H
3 BB
1 KRetired final 11 hitters
0.82 ERA through 2 starts
— Blake Harris (@BlakeHHarris) April 8, 2025
May didn’t fare much better with the Red Sox, as he had a 5.40 ERA in 28 innings. Now May is a free agent and is able to sign with any baseball team. Looking forward, he could be the perfect addition to the White Sox pitching staff.
Dustin May in his second Red Sox start:
6 IP, 5 H, 0 R, 1 BB, 8 Ks 🔥
Phenomenal performance when the team needed it the most. And if Dustin May can be a weapon for the Sox, it would change the entire conversation moving forward.
pic.twitter.com/IFNORDJflr— Gordo (@BOSSportsGordo) August 13, 2025
According to Spotrac, May’s market value is sitting at just under four million dollars. This is right in the price range for the White Sox, as May will likely want to sign a short term deal to build his value back up.
May is just 28 years old so he is still pretty young. He has been a very successful MLB pitcher for most of his career when he is on the field. The main problem for him has just been staying healthy and on the field. The White Sox and May could be a good fit, as May could eat a ton of low stress innings while rebuilding his value.
If May could stay healthy for the White Sox, he could earn himself a big payday in 2027. Additionally, if he has a strong first half, the White Sox could flip him at the deadline to a contender. The White Sox could use a veteran in their rotation and May could fit that role perfectly. There will be very few pitchers with May’s upside that won’t cost the White Sox a ton of money in free agency. Signing May could be a huge win-win for both parties.
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