Brewers Injury Twist Could Wreck Cubs Trade Deadline Plans

As injuries plague the Brewers' pitching staff, the Chicago Cubs find their 2026 trade deadline strategy potentially upended by shifting market dynamics.

The Milwaukee Brewers’ pitching staff has taken a hit, and Brandon Woodruff’s latest setback may end up mattering far beyond Milwaukee.

Woodruff is set to undergo a second shoulder surgery soon, which will shut him down for the rest of the 2026 season after only nine starts. That leaves the Brewers with a major gap in a rotation that was already drawing trade deadline attention.

Milwaukee has already been dealing with other injury concerns on the mound. Jacob Misiorowski missed his final first-half start because of fatigue, though he is slated to open the second half against former Brewers teammate Freddy Peralta on Monday.

Misiorowski said he feels “normal” and that the rest helped a lot. Still, with a fastball that regularly climbs north of 100 MPH and an arm built on effort, he’s the kind of pitcher the Brewers will be watching closely.

Left-hander Kyle Harrison has also been sidelined since early July with left forearm tightness. He had been a major boost since arriving in the Caleb Durbin trade with Boston, giving Milwaukee a strong one-two punch near the top of the rotation. The expectation is that Harrison could return soon, but Woodruff’s news is far less encouraging.

That matters in Chicago, too. The Brewers were already viewed as a possible player for a rotation upgrade at the deadline, and Woodruff’s injury only increases the odds they’ll be aggressive. That could put them directly in the Cubs’ way as Jed Hoyer tries to strengthen an injury-thinned staff of his own.

Tarik Skubal doesn’t seem like a realistic Cubs target if Detroit decides to move the Cy Young winner, but Freddy Peralta, Joe Ryan and Logan Webb are among the names that would fit. The Brewers could be in that same market as well, which only drives the price higher.

For Hoyer, that means a tougher road. If the Cubs want to catch Milwaukee, or at least set up another shot at them in October, he may have to move prospects with no clear everyday path and be willing to pay up to land impact arms.

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