Grading the Milwaukee Brewers' last three trade deadlines

It's not easy to pull off the perfect trade at the MLB Trade Deadline. Time constraints, imbalances of negotiating strength, and a scarcity of options often skew the true value of a player in favor of the selling team. In other words, it's difficult to add value at the deadline without overpaying.

However, on several occasions in the last three years, the Milwaukee Brewers' front office has expertly toed the line between adding key pieces and not parting with much prospect talent. Let's take a look at how each of the last three trade deadlines transpired for the Brewers and assign a letter grade to how the collection of trades from each year has aged since they occurred.

2024 Trade Deadline

Acquisitions: RHP Aaron Civale, RHP Frankie Montas, RHP Nick Mears

Subtractions: INF Gregory Barrios, OF Joey Wiemer, RHP Jakob Junis, RHP Bradley Blalock, RHP Yujanyer Herrera

The Brewers had a clear need at last year’s deadline: starting pitching. With only Freddy Peralta, Colin Rea, and Tobias Myers reliably making starts in the rotation, the team needed at least one starter at the deadline.

However, Matt Arnold and company didn't wait for the deadline to add a starter to the roster. Instead, he swung a very early deadline deal on July 3, acquiring Aaron Civale from the Tampa Bay Rays and sending infield prospect Gregory Barrios in return. Civale did exactly what was needed of him during his time with the Brewers: he ate innings. In 14 starts for the Crew, he tossed 74 innings, averaging more than five innings per start, and his 3.53 ERA to go along with it wasn't too shabby either. Despite not adding much value to the Brewers this season, back in June, Civale was flipped for Andrew Vaughn, who has been incredible during his brief time with the Brewers. That acquisition never would have happened had Arnold not acquired Civale last year.

Then, despite having a solid bullpen, the front office went out and acquired Nick Mears from the Colorado Rockies. Mears, who sported an ERA north of 5.00 at the time, was the perfect reclamation project for the Brewers, and the reward, if it paid off, was a back-end bullpen arm for several years to come. It's paid off and then some, as Mears has been one of the Brewers' best relievers in 2025, and figures to be a fixture in the team's bullpen for the next few years to come.

Finally, the day before the deadline, the Brewers made their most significant trade of the year, acquiring Frankie Montas from the Cincinnati Reds. Montas was seen as a higher ceiling, lower floor type pitcher in comparison to Civale, meaning while he had the potential to start a playoff game, he just as easily could've gotten hurt and missed the second half of the season. The former ended up being true, and Montas made a scoreless 3.2 inning start for the Crew in the postseason, serving the purpose that Arnold and company envisioned when they acquired him.

Meanwhile, the players that the Brewers gave up haven't done much for their new ballclubs. Junis was the best of the bunch, but the Brewers easily replaced him with another reliever, and the bullpen didn't miss a beat. All in all, the Brewers filled their needs admirably without losing significant prospect capital. The only thing they could've done better is be a bit more ambitious with the starting pitchers that they acquired. Doing so, perhaps would have raised the team's ceiling in the postseason.

Overall Grade: B+

2023 Trade Deadline

Acquisitions: OF/1B Mark Canha, 1B Carlos Santana, LHP Andrew Chafin

Subtractions: RHP Justin Jarvis, SS Jhonny Severino, RHP Peter Strzelecki

If you're looking for an example of a team that added meaningful production to their roster without losing hardly any prospect capital, turn to the masterclass that Matt Arnold and the Brewers' front office put on during the 2023 MLB Trade Deadline. The Brewers were desperate for consistency on offense, but had a strong clubhouse culture and an excellent defensive group that couldn't be jeopardized.

The deadline started with quite possibly the perfect addition: switch-hitting, veteran first baseman Carlos Santana, whose glove at the cold corner was just as strong as the consistent bat that he had displayed throughout his career. Santana fit in perfectly in Milwaukee, and he gave the Brew Crew exactly what they needed, a consistent presence in the middle of their lineup. He posted a 108 OPS+ with 11 HR in his 52 games in a Brewers uniform, all while playing excellent defense at first base.

Arnold's next move was acquiring veteran Mark Canha to man a corner outfield position, allowing the Brewers to push a struggling Joey Wiemer out of their everyday lineup. Canha was another perfect fit, not only for the team's culture but also on the field. He posted a 119 OPS+ during his 50 games in Milwaukee, and batted clean-up in each of the team's two playoff games. In fact, with Santana generally batting third, the Brewers completely re-shaped the middle of their order at the 2023 trade deadline, without sacrificing hardly any prospect capital.

The only real downside of the 2023 deadline was that the Andrew Chafin deal didn't pan out as the Brewers had hoped. Chafin posted a 5.82 ERA in 20 games for the Crew down the stretch in 2024 and missed out on the Brewers' postseason roster. That said, Strzelecki made just one appearance for the Arizona Diamondbacks before they released him, so no harm, no foul.

Overall Grade: A-

2022 Trade Deadline

Acquisitions: LHP Taylor Rogers, RHP Dinelson Lamet, OF Esteury Ruiz, LHP Robert Gasser, RHP Matt Bush, RHP Trevor Rosenthal

Subtractions: LHP Josh Hader, LHP Antoine Kelly, INF Mark Mathias, OF Tristan Peters

Here's where things get interesting. Most Brewers fans remember where they were when the team traded away their superstar closer while holding a three-game lead in the NL Central. It was a long-term play that tanked the team's short-term success. In other words, while it might have added more bites of the apple down the road, it snatched the apple out of the Brewers' hands in 2022.

Let's start with the return for Hader. Taylor Rogers, who was supposed to be Hader's replacement, posted a 5.24 ERA in 24 appearances during the second half of 2022 and blew 50% of his save opportunities in a Brewers uniform. Dinelson Lamet was designated for assignment two days after the trade. Esteury Ruiz turned out to be a worse prospect than evaluators initially believed him to be. And Robert Gasser looked promising in his first major league stint before undergoing Tommy John surgery last summer. If Matt Arnold hadn't saved this trade by turning Ruiz into William Contreras just four months later, Gasser would have been the only bright spot in a trade package for one of the best closers in Brewers history.

Meanwhile, the other two deals that the Brewers swung at the '22 deadline weren't much better. Matt Bush posted a 4.30 ERA in 25 appearances for the Crew in 2022, and was even worse when he stuck around for part of the 2023 season. And Trevor Rosenthal never even pitched for the Brewers in 2022, so the team essentially gave Tristan Peters, a promising outfield prospect, to the San Francisco Giants for nothing.

Missing the playoffs because you failed to make a trade at the deadline is one thing, but missing the playoffs because you sold your All-Star closer for an underwhelming return is inexcusable. The only thing keeping this deadline from an "F" grade is what Matt Arnold was able to turn Esteury Ruiz into the following December. In a three-team deal with the Oakland Athletics and Atlanta Braves, the Brewers gave up Ruiz, and walked away with All-Star catcher William Contreras. That, paired with the promise that Gasser has shown, raises the grade. But had the Athletics not been interested in Ruiz or the Braves weren't interested in giving up Contreras, the 2022 deadline would have been a total miss.

Overall Grade: C-