Reviewing Brewers’ Biggest Trades in 2026

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Now that the World Series festivities have started to cool off, it’s only natural to reflect on the season with rose-tinted glasses. When one thinks of all the moments that ultimately led to Milwaukee’s triumph, the ones that stand out are often roster changes. The arrival of new faces can often be exciting, as the feeling of the unknown allows each fan to predict how they think each player will help (or hurt) the team’s cause.

Fortunately, now that we live in the future, we can easily look back on the major deals that the Brewers struck and reflect on whether they were wins, losses, or something in between. For the sake of this article, we will only be looking at the most significant moves (if you’d like to discuss the aftermath of the Joel Kuhnel trade, feel free to start a forum thread!) and will primarily be focusing on what was delivered this year.

February 9: Milwaukee Brewers trade Caleb Durbin, Andruw Monasterio, and Anthony Seigler to the Boston Red Sox in exchange for Kyle Harrison, Shane Drohan, and David Hamilton

Milwaukee sent almost all of their third-base depth to Boston. In return, they received two left-handed pitchers and a utility infielder. At first, this deal was surprising. Caleb Durbin had a really strong rookie campaign, placing third in NL Rookie of the Year voting, and he was a Pat Murphy favorite. Anthony Seigler was a Brewer Fanatic favorite and had a lot of potential that was often overshadowed by poor batted-ball luck. Andruw Monasterio had been on the team for years and finally looked like he was starting to put things together in 2025.

On paper, the return value didn’t seem exciting for the Brewers. In 2024, Kyle Harrison was the Giants’ No. 1 prospect and the No. 23 prospect overall, but he hadn’t quite lived up to the hype. Shane Drohan had yet to pitch in the majors, though he'd posted solid numbers in Triple-A in 2025 over a small sample. David Hamilton posted an OPS+ of just 63 in 2025. Overall, it seemed like a mystery why the Brewers were giving up enough third base depth to end up having to rely on Luis Rengifo.

This ended up being a rare win/win trade for both parties. Harrison had a great first half, and though his numbers after the All-Star break were shaky enough to demote him from No. 2 in the rotation to nowhere to be seen in the playoffs, it seems like Milwaukee had discovered the recipe for how to make him great: using the slurve to keep hitters off of his fastball, and throwing that fastball with a bit more carry.

Drohan wasn’t too shabby in his rookie year, either, pitching to a 4.19 ERA with a 3.73 FIP over 124 ⅔ innings. He made 19 starts and 14 relief appearances, even managing to accumulate two saves. He’s got more work to do before cementing his place in Milwaukee’s rotation, but he had his moments, and most importantly, he provided much-needed innings.

Hamilton became a textbook “scrappy” player, doing whatever was needed to help his team win. He led MLB in sacrifice hits (13), was a solid defender at third base and shortstop, and posted a .950 OPS with two home runs in the Brewers’ postseason run.

For the Red Sox, this trade got off to a brutal start, as Durbin was one of the worst qualified hitters in baseball for a while. Fortunately, he ended the year as a worthy successor to Alex Bregman, accumulating 4.4 rWAR thanks to league-average offense combined with Gold Glove defense. Though they didn’t have full-time roles, Seigler and Monasterio carved out niches of their own.

At the end of the day, both organizations got their hands on a few young players with years of control remaining. It wouldn’t be surprising to see all six of the players involved continue to take on more responsibility for their respective rosters.

August 3: Milwaukee Brewers trade Alexander Frias and Josiah Ragsdale to the St. Louis Cardinals in exchange for Dustin May and JoJo Romero

This was a spicy trade for two reasons. First, many felt that it was an overpay. Frias and Ragsdale were the organization’s No. 8 and No. 22 prospects, respectively, but they were both having breakout seasons in the minors. At 18 years old, Frias posted a 189 wRC+ with an absurd .441 average and .518 on-base percentage in 137 plate appearances in the Arizona Complex League. Before being traded, Ragsdale had a 184 wRC+ with 12 home runs in 119 Double-A plate appearances.

Second, this was a rare trade with a division rival. These two organizations don’t often do business with each other, for obvious reasons. If the deal were to end up lopsided, it’d be a price they’d have to pay for 13 times a year. They last made a deal in 2015 that swapped reliever Jonathan Broxton for outfield prospect Malik Collymore. Nonetheless, the front office saw something they liked in Dustin May, who had a 4.38 ERA and 3.15 FIP across 21 starts for St. Louis. JoJo Romero had also been solid out of the bullpen, with a 3.35 ERA.

To most people, the May acquisition didn’t really pan out. He struggled immediately with the Brewers and finished his last 10 starts with a 5.65 ERA and 5.06 FIP. He was arguably the least effective pitcher of the team’s playoff run, pitching to a 5.73 ERA over 11 innings. Despite being the headliner of the trade, he was quickly overshadowed by Romero, who didn’t make his Milwaukee debut until September due to injury. Romero was as advertised in the regular season but dialed it up to 11 in the playoffs, posting a stellar 1.13 ERA and making even the toughest opposition look outmatched.

Both Frias and Ragsdale cooled off after joining the Cardinals organization, but since both are still early in their professional careers, the worst could still be yet to come. Both May and Romero have returned to free agency, but with the latter playing a vital role in delivering Milwaukee its first championship, it’ll be worth a few years of regular season pain from these two prospects if they end up making it to the show.

August 3: Milwaukee Brewers trade Mark Manfredi and Juan Martinez to the Colorado Rockies in exchange for Antonio Senzatela

For the first half of the season, Antonio Senzatela was doing the impossible: pitching well at Coors Field. Following several underwhelming seasons as a starter marred by Tommy John and rough numbers, he moved to the bullpen for the first time and loved it, posting a 3.61 ERA and 3.37 FIP in 52 ⅓ innings for the Rockies.

Naturally, this interested the Brewers, who invested heavily in multi-inning relievers this season—a decision that would pay dividends in the postseason. Senzatela’s regular season was confusing, as he reverted to bad habits and an outdated pitch mix that led to subpar results in Milwaukee. Fortunately, he turned it around and was scoreless in his 4 ⅓ postseason innings.

Neither of the prospects that the Rockies received were ranked in the Brewers’ Top 30, but they still proved their worth. Mark Manfredi worked his way to a debut and eventual solid stint with the Rockies, making 14 appearances and maintaining a 3.06 ERA with a 3.55 FIP.

Juan Martinez struggled with High-A competition when he was in the Brewers system, but after moving to Colorado, he had a respectable 109 wRC+ over 104 plate appearances and is now ranked as the organization’s No. 25 prospect. At just 19 years old, it’s far too early to see whether he’ll end up being a pillar of the Rockies’ lineup, but even if he ends up being a star, it'll be hard to blame the Brewers for having been willing to move him.

Overall, this trade was a solid addition for both. The Rockies got a decent reliever and a potentially promising infielder for the future, while the Brewers got more depth in their relief unit. That allowed them to, at the very least, manage their bullpen more aggressively in playoff situations. Milwaukee has already declined Senzatela’s option, making him a free agent, so like the May/Romero trade, we’ll have to wait a few years to really see who got the better end of this deal. But then again, we know. The Brewers have a trophy already. These deals have already paid the dividends the team was pursuing, and they'll keep getting value from one of them for several more years.