The Cubs are at least kicking the tires on Dustin May, even if the fit comes with a built-in reminder of what the Brewers already found out the hard way.
May is on Chicago’s radar this offseason, according to Jon Morosi, who reported that the free-agent right-hander is drawing interest from a wide group that includes the Cubs, White Sox, Padres and Astros. The note about Houston is a little extra wrinkle: new Astros GM Randy Flores was in the Cardinals front office when they signed May last offseason.
For the Cubs, the appeal is obvious enough. May, 29, still carries the kind of fastball that keeps teams coming back for another look, and his early career with the Dodgers suggested he could become a regular in a big-league rotation.
But the road since then has been messy. His injury history pushed him out of the picture in Los Angeles, which led to a trade to the Red Sox before the 2025 season.
He then opened the 2026 campaign with the Cardinals before getting moved to Milwaukee at the deadline. That stop did not go the way the Brewers hoped. May posted a 5.65 ERA in 10 starts with Milwaukee and eventually fell out of their rotation plans during their World Series run.
That’s what makes Chicago’s interest feel a little ironic. The Cubs may be betting they can get more out of May than the Brewers did, but it also hints at the kind of offseason they may be building toward. The goal is to add three established starters before the start of the 2027 season, and the sense is that Chicago could lean more toward accumulating arms than landing one true headliner.
In that sense, May would make sense as the third piece, not the answer. He fits more as a swing-for-upside addition, similar to what the Cubs may be expecting from Edward Cabrera moving forward.
If it clicks, he could become one of those surprise contributors that changes the shape of a season. If it doesn’t, the rotation still needs more.
There is still enough there to understand why teams are interested. Baseball Savant lists May’s fastball velocity in the 85th percentile, and his extension is in the 72nd percentile.
Those traits explain why clubs keep circling back and why the Cubs appear willing to take a look. But if this offseason is going to be judged a success for Jed Hoyer and the front office, May alone won’t be enough.
In Other News...
Cubs Outfield Picture Is Taking Shape Around One Intriguing Name
The Cubs outfield is one of the more interesting roster puzzles on the board this winter, with Pete Crow-Armstrong already locked into center and two more spots suddenly in play. Ian Happ and Seiya Suzuki are both headed for free agency, which has opened the door for a different kind of conversation around the rest of the roster, including whether the answer might come from inside the organization rather than from outside additions.
Among the internal names, Pedro Ramirez has emerged as the most intriguing one to watch. GM Carter Hawkins has pointed to Ramirezs athleticism and versatility, traits that fit the kind of flexibility the Cubs may need as they sort through the outfield mix. Matt Shaw and Kevin Alcantara are also in the conversation, and the broader picture around the club keeps evolving with Jed Hoyers extension through 2030, the possibility of a Carson Kelly return, and a few notable front-office and player-development moves that show how much of the organization is being shaped at once. [Read more 🡒]
Cubs Rotation Need Could Push Jed Hoyer Toward A Different Plan
The Cubs offseason pitching search is shaping up to be more than a single splash move, and that could push Jed Hoyer toward a broader, budget-conscious plan. With the rotation still needing help, the front office is weighing a mix of trade targets and free-agent additions rather than banking on one big answer to solve the problem.
Among the names that fit that approach are Walker Buehler, Erick Fedde, Lucas Giolito and Chris Paddack, all pitchers whose recent track records make them plausible fits if Chicago wants to spread its resources around. The appeal is obvious: the Cubs need multiple arms, and the market may reward teams willing to look for value instead of chasing the most expensive option available. [Read more 🡒]
Cubs Still Need This Bat While Other Teams Start Moving
The Red Soxs decision to lock up Jake Bauers on a four-year, $56 million deal took one more name off the board for teams still sorting through their offseason plans, and it offered a reminder of how quickly the market can move once a club decides it wants a bat. Bauers had been viewed as a likely departure from Milwaukee after the Brewers extended him a qualifying offer, so Bostons move closes another door for contenders looking to add offense.
For the Cubs, the timing matters because their own offseason priorities remain unresolved and the lineup still needs help. Chicago has not made any significant moves yet, and every signing elsewhere only sharpens the pressure to find the right fit before the best options disappear. [Read more 🡒]