Dustin May looks like exactly the kind of arm Jed Hoyer can talk himself into, but the Cubs can’t let that be the whole plan.
That’s the basic shape of the conversation around the former Dodgers right-hander, who is now a free agent after a 2026 season split between the St. Louis Cardinals and Milwaukee Brewers.
The Cubs probably should have been in on him when Los Angeles moved him out of its pitching plans, but instead he went to Boston before winding up in the NL Central. Now he’s back on the market, and Chicago figures to come up again.
The appeal is obvious. May has the kind of fastball the Cubs like to build around, and it has real life in it.
During the 2026 season, his heater ranked in the 82 percentile in run value and sat in the upper 90s. That kind of velocity is hard to ignore, especially for a Cubs rotation that could use more of it.
If the organization can get him back to living at the bottom of the zone and pounding the ground ball the way he did early in his career, there’s a path to this looking like a smart, low-cost swing.
But the floor matters here, too. May has been trying to rediscover the version of himself that flashed with the Dodgers, and the results have still been uneven.
There was a stretch with the Cardinals when it looked like something might be turning, but he still finished with a 4.38 ERA in 21 starts before the trade. Then with the Brewers, he posted a 5.65 ERA in 10.
That’s why May makes sense only as part of a bigger pitching push, not as the answer. If the Cubs land a major arm such as Michael King, and perhaps bring back both Clay Holmes and David Peterson, then adding May on top of that would deepen the staff in a meaningful way. In that kind of winter, he becomes a worthwhile project for Hoyer and his group.
And the Cubs have to think that way because the uncertainty ahead is real. Nobody knows what version of Justin Steele will be there when he takes the mound in 2027.
Cade Horton is expected to miss most, if not all, of the season, and Ben Brown’s neck injury could keep him from being a full-time rotation piece. Edward Cabrera could also end up being a miss.
So yes, May fits the familiar Jed Hoyer gamble. Just not as the only one.
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Cubs May Have No Choice But To Chase Pitching Another Way
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Pitching may be the area that offers the cleanest path forward, but even there the choices are complicated. Tarik Skubal and Freddy Peralta are among the names that could shape the market if the Cubs choose to pursue help on the mound, yet Jed Hoyer may have to lean on trades and creative maneuvering instead of simply shopping in free agency. With collective bargaining talks still hanging over the sport and a possible lockout in the background, the timing only adds another layer to a winter that already looks tricky. [Read more 🡒]