Shelby Miller Heads to the Cubs on Multi-Year Deal After Injury-Shortened Brewers Stint
The Milwaukee Brewers played things close to the vest at the 2025 trade deadline, and for good reason. They were surging when July 3 rolled around, and instead of making a blockbuster move, the front office focused on shoring up the edges of an already strong roster. It was a calculated approach-one that brought in depth and experience without sacrificing the farm.
Among the moves: Milwaukee upgraded its catching depth by acquiring veteran Danny Jansen from the Rays, sending infield prospect Jadher Areinamo the other way. They also leveraged their surplus of starting pitching, shipping Nestor Cortes and prospect Jorge Quintana to San Diego in exchange for outfielder Brandon Lockridge-a speed-and-defense addition who gave them some flexibility in the outfield.
But the most intriguing move came just before the deadline buzzer, in a deal that raised eyebrows across the league. The Brewers landed reliever Shelby Miller and lefty starter Jordan Montgomery from the Diamondbacks without sending a single player in return.
How? By agreeing to absorb a portion of Montgomery’s remaining salary-he was injured at the time-Milwaukee essentially bought themselves a high-leverage bullpen arm in Miller without giving up prospect capital.
It was a smart, low-risk gamble by Matt Arnold and the Brewers' front office.
For a brief window, it looked like a steal.
Miller, who was already managing a forearm strain when he arrived in Milwaukee, made 10 appearances in August. Nine of them were lights-out.
He brought late-inning stability and gave the Brewers another weapon in tight games. But on September 1, everything changed.
Facing the Phillies, Miller felt something give in his elbow. He knew right away-it was bad.
He was headed for his second Tommy John surgery.
Fast-forward to today, and Miller is on the move again. The 35-year-old has signed a multi-year major league deal with none other than the Chicago Cubs-Milwaukee’s longtime division rival. The terms of the deal haven’t been made public yet, but it’s expected to be a short-term pact, likely no more than two years, given the uncertainty around his recovery timeline.
Miller won’t pitch in 2026. That much is clear.
Recovering from a second Tommy John at his age is no small task. But the Cubs are betting on the upside-on what he might still have left in the tank by 2027.
And there’s reason to believe he could still be a factor.
From 2024 through 2026, Miller posted a 3.13 ERA while averaging more strikeouts than innings pitched and keeping walks to a minimum. He was a steady presence out of the bullpen for both Arizona and the Dodgers before the injury, averaging 45 appearances per season and flashing a fastball that still touched 95 mph. Even if he loses a few ticks post-surgery, his splitter-arguably his best pitch-remains a weapon.
This is the kind of move a big-market team like the Cubs can afford to make. If Miller returns to form, they’ve added a battle-tested reliever with late-inning experience.
If not, the financial hit is manageable. Either way, it adds a layer of intrigue to the Cubs-Brewers rivalry.
Milwaukee took the initial swing, but Chicago may be the team to benefit long-term.
For now, the Brewers are left with a what-could-have-been. Miller gave them a glimpse of his value before the injury cut things short. And now, he’ll be rehabbing in enemy territory, hoping to make his return to the mound in 2027-this time in Cubbie blue.