flag
back Back
Cubs Free Agency: Dustin May Reportedly on Their List, But How High?

The Chicago Cubs may have Dustin May circled on their wishlist as they look to up their velocity.

Oct 27, 2026; St. Petersburg, Florida, USA; Milwaukee Brewers pitcher Dustin May (21) throws a pitch against the Tampa Bay Rays during the first inning in game four of the 2026 World Series at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

It may not be Tarik Skubal or Michael King ... but it's a start.

As teams scramble to fill roster voids before the MLB lockout pauses offseason action, the Cubs have their sights set on fixing their starting rotation. A long list of North Side arms have hit the open market this fall, including Shota Imanaga, Matthew Boyd, Clay Holmes, Kevin Gausman, and David Peterson. While the Cubs will likely bring back at least one familiar face, there is no question that some new names will be on the mound in 2027.

With that said, according to Jon Morosi, we now have one specific name to keep an eye on. Righty Dustin May is reportedly on the radar of several teams, with the Cubs joining the Padres, Astros, and their South Side rivals.

Would Dustin May Be a Good Fit for the Cubs?

Oct 27, 2026; St. Petersburg, Florida, USA; Milwaukee Brewers pitcher Dustin May (21) walks back to the dugout after being relieved during the fourth inning against the Tampa Bay Rays in game four of the 2026 World Series at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

First of all, if Dustin May is near the top of the Chicago Cubs' priority list, that's going to be a problem. Jed Hoyer and his front office must set the bar higher after watching their offense and defense rank near the top of the league. Find a true ace, and there is certainly reason to believe the Cubs can reach new heights in 2027.

If May is viewed as the Cubs' third or fourth option for next year's rotation, that's a far more palatable path. Since really seeing an uptick in his starts during the 2025 campaign, May has been middling at best. He held a 4.96 ERA two seasons ago with the Dodgers and Red Sox before starting 2026 with the Cardinals. After starting 21 games for St. Louis, he was sent to be part of the World Series-winning Milwaukee Brewers.

Overall, May threw a 4.70 ERA in his career-high 31 starts. This included tossing just a 5.10 ERA in his ten regular-season outings with the Brewers. May appeared in five postseason games, starting only two. His final performance came on October 27 in the Brewers' one World Series loss. May got the start and went 3.0 innings, giving up two earned runs to the Tampa Bay Rays.

May is only 29 years old and has certainly garnered some good MLB experience over the years. He's also operated as an effective groundball pitcher in the past, which we all know is right up the Cubs' alley. The versatility is a big part of the appeal, as well. May had a balanced attack this past season, relying heavily on a mix of four pitches: Four-seamer, cutter, sinker, and sweeper. We also saw him mix in a curveball and change up at times against lefties.

His fastball and sinker sit in the mid-90s, which would add something new to the Cubs' rotation. They have seemingly accepted the fact that they finally need to increase their velocity, and May can help make that happen.

Still, it's hard to say that May would be a significant difference-maker for this Cubs team. Might they be able to bring the best out of him, especially in front of this elite defense? It's not out of the question, but his struggles with the Brewers raise some concerns, as does the fact that he's been on the move so often the last couple of years.

Once again, if May is a move, you can live with that. If May is the free-agency move, the Cubs could have a problem.

You may like

Brewers Sign 22-Year-Old Fireballer After Two-Year Nationals Stint

si.com 43 minutes ago

Grading each of ESPN’s ‘perfect’ MLB free agency moves, including Skubal to the Mets

fansided.com 1 hour ago

Diamondbacks Sign Former Cubs Top Prospect to Boost Pitching Depth

si.com 26 minutes ago

What to Do With Bowman Red Rookie Redemptions of Sal Stewart and Kevin McGonigle

si.com 2 hours ago

New Rumor Offers NY Yankees Chance at Dream Trade Target: What Could a Blockbuster Deal Cost?

aol.com 3 hours ago

MLB Finally Admitted What We Already Knew About Gabriel Moreno

si.com 54 minutes ago

Pros, Cons of Cardinals Potentially Signing Zac Gallen

si.com 1 hour ago

Four Teams Emerge As Red Sox-Jarren Duran Trade Buzz Intensifies

si.com 1 hour ago

Everything to Know About Southern Miss Baseball's 15 Signees for 2028 Season

si.com 1 hour ago