The starting-pitching market is taking shape as MLB teams evaluate options ahead of the 2027 season. Several organizations are expected to strengthen their rotations, with younger free agents offering a chance to add talent without pursuing the most expensive names.
Dustin May is entering another important offseason after spending the 2026 campaign with multiple organizations. The right-hander started the year with St. Louis, then was traded to Milwaukee at the deadline. He also played for the Dodgers and Red Sox.
At 29, May remains an interesting option because of his velocity, pitching ability, and recent workload. However, his injury history and inconsistent results could influence his market as teams consider their rotation needs.
Cubs, White Sox, Padres and Astros Show Interest in Dustin May
The Chicago Cubs, Chicago White Sox, San Diego Padres and Houston Astros are among the teams showing interest in Dustin May, according to MLB Network insider Jon Morosi. The 29-year-old right-hander is one of the youngest starting pitchers available in free agency this offseason.
Of note, new Astros GM Randy Flores was in the Cardinals front office when they signed May last offseason.
May, 29, is one of the
Morosi also highlighted a possible connection between May and Houston. New Astros general manager Randy Flores was part of the Cardinals‘ front office when St. Louis signed May last offseason.
That history could make the Astros an interesting team to watch.
Flores already had a chance to evaluate May while with the Cardinals, though there is no indication Houston has made a formal offer.
The Cubs are another team that could benefit from adding May. Their rotation needs multiple starters, making the right-hander a potential option as they look for depth.
The Cubs have been discussed in offseason analysis, but not confirmed as a separate pursuit. Morosi reports Chicago is interested, though no contract talks are confirmed.
The White Sox and Padres are also part of the reported group. Their interest gives May several potential destinations as he evaluates his options.
May’s age is an important factor in his free-agent appeal. He has the velocity and pitching tools teams continue to value, even though his results haven’t always matched his potential.
His recent performance and medical history, however, could determine how much teams are willing to invest in him.
Dustin May’s 2026 Numbers and Contract Outlook
May recorded 145.2 innings with a 4.70 ERA in 2026. His underlying numbers were more encouraging; he finished with a 3.63 FIP, suggesting his results may not have fully reflected his pitching.
His availability has improved over the past two seasons. May underwent two UCL reconstructions from 2021 to 2024, limiting his development and time on the mound.
After returning, he managed 132.1 innings in 2025 and followed that with another full workload in 2026. That recent durability could help his case as teams look for starting-pitching depth.
According to “MLB Trade Rumors,” May could get a two-year, $30 million deal with a player opt-out after year one, giving him a chance to rebuild his value while limiting the team’s commitment.
The Cardinals could also remain an option. St. Louis reportedly has interest in bringing May back after trading him to Milwaukee at the deadline.
However, the organization may be reluctant to offer the multi-year contract he is seeking as it continues its rebuilding process.
May’s market could therefore depend on which teams are willing to invest in his potential despite his injury history.
His velocity, age, and recent workload make him an appealing option, but his 4.70 ERA also underscores the uncertainty.
With four teams already linked to him, May has several possible landing spots. The next stage of free agency will determine whether any of them are willing to offer the contract he wants.
Former Dodgers Starter Draws Interest From 4 MLB Teams