The rivalry between the Chicago Cubs and Milwaukee Brewers has grown into one of the fiercest in the National League Central, fueled by geographic proximity and years of close contention for the division crown.
Games between the clubs often carry extra intensity, with fans packing ballparks and the teams trading blows in key series that can shape playoff races.
As the offseason gets underway, the Cubs face a clear need to strengthen their starting rotation after injuries and the departure of several arms left the staff thin heading into 2027.
According to MLB Network reporter Jon Morosi, the Cubs are among the clubs showing interest in free-agent right-hander Dustin May, who spent the second half of the 2026 season with the Brewers after a midseason trade from the Cardinals.
May, who declined a mutual option to become a free agent, helped Milwaukee capture its first World Series title before hitting the open market at age 29.
Landing the pitcher would amount to the Cubs pulling a starter away from their longtime division rival just months after he contributed to a championship run in Milwaukee.
Morosi reported that May is drawing attention from a wide set of teams, with Chicago among those linked to the right-hander as he seeks a multiyear deal.
May made 31 starts in 2026 split between the Cardinals and Brewers, finishing with a 7-9 record, a 4.70 ERA and 144 strikeouts in 145 2/3 innings.
His results were less consistent after the trade to Milwaukee, where he posted a higher ERA in limited starts before appearing in the postseason.
Still, the 6-foot-6 right-hander showed improved velocity and strikeout numbers compared with prior seasons, and he stayed healthy enough to take the ball regularly.
As one of the younger starting pitchers available this winter, May offers a chance for a team to add innings without committing to an older veteran on a long-term contract.
The Brewers acquired him from St. Louis in August alongside another arm, and he contributed to their deep playoff run even if his overall numbers were uneven.
For the Cubs, adding May would address rotation depth while also creating a storyline that could rankle fans in Milwaukee, given the heated nature of the series between the two clubs.
Chicago has already seen its manager Craig Counsell cross from the Brewers dugout, and signing a recent Milwaukee pitcher would further blur the lines in the rivalry.
Other clubs including the White Sox, Padres and Astros have also been connected to May, but the Cubs angle stands out because of the direct competition in the NL Central.
May previously won a World Series with the Dodgers in 2020, giving him two championship rings as he enters free agency looking for a better contract than the one-year deal he signed last winter.
Whether the interest from Chicago turns into a serious pursuit remains to be seen, but the mere link highlights how the Cubs are scanning the market for arms that could help them close the gap on their rivals.
