Cubs' chances of stealing a Brewers' fan favorite just took a serious hit

The rivalry between the Milwaukee Brewers and the Chicago Cubs has never been stronger. Milwaukee has put the National League Central in a stranglehold, winning the division in four of the last five seasons. This year, they vanquished the Cubs in Game 5 of the NLDS, punching their ticket to a League Championship matchup with the Los Angeles Dodgers.

Craig Counsell jumping ship to join the Cubs following the 2023 season only added fuel to the fire, with the longtime Milwaukee staple now taking the role of Benedict Arnold in the eyes of Brewers fans. With all that in mind, what better way to add insult to injury than to lure two-time All-Star Brandon Woodruff to rejoin his former manager in Chicago next season?

Brandon Woodruff receives a qualifying offer from the Brewers

It remains a possibility, but after Milwaukee extended a qualifying offer to its longest-tenured player on Thursday, those odds took a major hit. Should Woodruff decline, he'll be tied to draft pick compensation in free agency - something Jed Hoyer and the Cubs haven't been keen on offering up in recent years.

Offering the $22 million qualifying offer is a risky gamble for a team like the Brewers. The biggest issue is Woodruff's health. In 2023, he underwent shoulder surgery. That cost him the entire 2024 campaign and a chunk of the 2025 season, as well. He looked sharp upon his return, working to a 3.20 ERA in a dozen starts before a lat injury ended his season and kept him off the team's postseason roster.

Since the start of the 2021 season, Woodruff has pitched to a 2.77 ERA, 3.12 FIP and 0.971 WHIP - elite numbers, and ones that would surely intrigue a team in need of rotation help like the Cubs. The problem is that he's started just 80 games during those five years, averaging just 116 innings per season. So the work has been good, but there just hasn't been enough of it.

Still, even if he rejects the QO, his checkered health history and age (he's heading into his age-33 season), he's unlikely to fetch a huge payday on the open market. The Cubs have notoriously avoided long-term deals for pitchers and picking up Woodruff while hoping for a bounce-back, similar to how they brought Matthew Boyd in last winter makes some degree of sense.

So is it likely? No, probably not. But it would add an interesting wrinkle to an already-potent Cubs-Brewers rivalry.