The Milwaukee Brewers and Chicago Cubs are heading into 2026 with two very different blueprints - and the contrast couldn’t be clearer.
Milwaukee has leaned hard into a long-view strategy this offseason, dealing away contributors like Isaac Collins, Freddy Peralta, and Caleb Durbin for future upside. It’s a classic rebuild move: sacrifice current talent to stockpile potential. Meanwhile, the Cubs are doing the opposite - pushing chips to the center of the table and betting big on the now.
They’ve already made major noise by landing third baseman Alex Bregman in free agency and acquiring right-hander Edward Cabrera via trade. But they might not be done yet.
According to reports, the Cubs are one of four teams in the hunt for Zac Gallen, the former Arizona Diamondbacks ace and arguably the top remaining free-agent arm on the market. The Padres, Orioles, and Diamondbacks are also reportedly in the mix, but the Cubs’ involvement is especially intriguing - and a bit surprising.
On paper, Chicago’s rotation already looks well-stocked. The current group features Matthew Boyd, Shota Imanaga, Cade Horton, Cabrera, and Jameson Taillon, with Justin Steele expected to return from injury and Colin Rea still in the mix after a career-best 2025. That’s a solid, flexible group with a mix of veteran savvy and young upside.
So why chase Gallen?
Well, even after a down year, Gallen brings something few pitchers can: a proven track record of frontline production. He’s coming off a rough 2025 - 13-15 with a 4.83 ERA, 31 homers allowed in 192 innings, and just a 1.1 WAR.
But that stat line doesn’t erase what he’s done in the past. From 2022 through 2024, Gallen was a legit workhorse, compiling a 43-19 record with a 3.58 career ERA and a strikeout rate of 9.5 per nine.
Over that three-year stretch, he racked up 12.2 WAR across 93 starts - elite-level production by any measure.
Yes, he took a step back last season. But if he can bounce back - and at age 30, that’s still very much on the table - he could elevate the Cubs’ rotation from solid to scary.
Financially, Gallen won’t come cheap. His market value is projected north of $18 million per year, and that’s on top of the $175 million deal Chicago already handed Bregman.
But the Cubs seem willing to spend to win. Losing Kyle Tucker to the Dodgers left a hole in their lineup, and they’ve responded by going aggressive - first with Bregman, then with Cabrera, and now potentially with Gallen.
This isn’t a team dipping its toe in the water. It’s a team diving in headfirst.
Adding Gallen would be a bold move - maybe even a luxury given the current rotation depth - but it also fits the pattern of a club that believes its window is open right now. If Gallen returns to form, the Cubs could be looking at one of the most balanced and dangerous pitching staffs in the National League.
And for a franchise that hasn’t shied away from making headlines this winter, one more splash wouldn’t be out of character.