The Milwaukee Brewers have taken a patient approach this offseason and still have room in their budget as the free-agent market narrows. Could they find a creative way to secure a top-tier starter to bolster their rotation?
Jack Flaherty, once projected by MLB Trade Rumors to land a five-year, $115 million deal after a strong 2024 season with the Dodgers, now finds himself in a different position as February approaches. Concerns about his back, which affected trade talks last summer, linger for some teams. However, Flaherty delivered a solid season with 28 starts, 162 innings pitched, a 3.17 ERA, and 29.9% strikeouts, followed by a strong postseason run.
Sources suggest a deal of that earlier magnitude is no longer on the table, but a three-year contract resembling Yusei Kikuchi’s ($63 million) or Luis Severino’s ($67 million) recent deals is more plausible. Flaherty may prefer a more flexible structure, making him an intriguing option for the Brewers, who need rotational stability and have some financial flexibility.
One potential framework for a deal with Flaherty could involve:
- $15 million in 2025
- A $25 million player option for 2026, with a $5 million buyout
This structure would essentially create a two-year, $40 million commitment, similar to Jordan Montgomery’s one-year, $25 million deal with vesting options last year. While Flaherty has higher upside than Montgomery, his durability and consistency remain concerns.
From Milwaukee’s perspective, such a deal has added advantages. If Flaherty opts out after 2025, the Brewers could extend a qualifying offer, securing draft pick compensation if he declines. Conversely, if he struggles or gets injured and opts in for 2026, the Brewers may still benefit, as they are likely to trade Freddy Peralta next offseason and face potential free-agent losses in Aaron Civale, Nestor Cortes, and Brandon Woodruff. With several young pitchers developing, the Brewers could use a veteran presence like Flaherty in 2026.
Flaherty’s pitching profile aligns with the Brewers’ preferences—deceptive four-seam carry, two breaking balls, and a lower arm slot. They showed interest in him last year before pivoting to Frankie Montas. A deal now could solidify the roster while allowing the Brewers to explore other moves, such as trading Civale for infield depth. A partnership between Flaherty and the Brewers could be mutually beneficial, similar to the team’s success with Rhys Hoskins last January.
