But as Bassitt heads into his age-37 season, he’s not going to command a long-term commitment (one to two years, maximum). The Brewers tend to get creative on how they structure these types of deals, and if his AAV can settle in the $12 million to $15 million range, he should be in Milwaukee’s price range.
It’s not flashy, but it does feel like the picture-perfect fit in so many ways. If the Brewers do spend on a player this winter, Bassitt checks all the boxes of an arm that could thrive in Milwaukee.
Chicago Cubs Swing Big Trade For Frontline Arm Joe Ryan
MINNEAPOLIS, MN – JULY 26: Joe Ryan #41 of the Minnesota Twins pitches during the first inning against the Washington Nationals on July 26, 2025 at Target Field in Minneapolis, Minnesota. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images)
The Chicago Cubs have a very important offseason ahead of them. They’re, in all likelihood, losing superstar Kyle Tucker to free agency, but they are in a window where they can absolutely compete for the National League pennant with how lethal their lineup is.
Additions need to be made to dethrone the Brewers at the top of the division, though, and the starting rotation is where they can make that meaningful big splash.
Looking at the Cubs’ current rotation, it lacks star power. Matthew Boyd was an All-Star in 2025 and a savior in the rotation, but he is entering his age-35 season, will be coming off nearly 180 innings pitched — which is his most thrown in a single season since 2019 — and slowed down at the end of 2025 with a 4.63 ERA after the All-Star break.
Shota Imanaga too hit a wall with a 4.70 ERA in the second half, leading to the Cubs declining his club option before offering him the qualifying offer — a contract in which they likely did not anticipate he’d accept. Nonetheless, he did accept the QO and will return to the rotation in 2026, but he comes with question marks.