Brewers might need to deviate from typical trade deadline plan to combat Dodgers

The only thing that's stood in the way of the Milwaukee Brewers making two World Series appearances in the last eight years is the Los Angeles Dodgers.

Back in 2018, as the Brewers were just opening their ongoing window of competitiveness, the Dodgers, led by midseason trade deadline acquisition Manny Machado, defeated them in the National League Championship Series by winning a tense Game 7 in Milwaukee. Then, in 2025, led by Shohei Ohtani, who crushed three homers and struck out 10 batters on the mound in Game 4, the Dodgers once again prevented the Brew Crew from reaching the Fall Classic, sweeping Milwaukee in four games in the NLCS.

Roughly two and a half months into the 2026 campaign, the Brewers and Dodgers once again look like they will be competing for a National League pennant. While a resurgent Atlanta Braves team currently holds the best record in baseball and leads the National League East by a healthy 7.5-game margin, the Brewers and Dodgers are once again leading their respective NL divisions, with sizable cushions.

As trade rumors start to swirl, despite the midseason trade deadline still being more than a month away, the Brewers are once again facing a question that they've been met with many times during their ongoing Golden Age: is this the season in which they should go "all-in" and acquire a game-changing talent at the trade deadline?

To overcome the hurdle that is the Los Angeles Dodgers, Brewers will need a significant acquistion at the trade deadline

There are several components to the question that need answering, or at least require more context. First, is the answer to the question "why this season as opposed to past or future seasons?" In regard to past seasons, this Brewers team has the advantage of having one of the most dominant pitchers in the entire sport in Jacob Misiorowski and a strong No. 2 starter in Kyle Harrison -- something they certainly didn't have in 2018 or 2025. Milwaukee has had strong rotations in past years, particularly the 2021 team which was led by a big three of Corbin Burnes, Brandon Woodruff, and Freddy Peralta. However, the Brewers' offense in 2026 is far better than it was five years ago, suggesting that Milwaukee wouldn't meet a similar fate to their 2021 postseason run, which ended due to a lack of runs.

The attention then turns to "why this year as opposed to future seasons?" which is a far more difficult question to answer. The Brewers currently only have one impending free agent on their 26-man roster, Jake Bauers. Their farm system is the best in all of baseball. Assuming their group of young starting pitchers only continues to develop and their top-ranked position player prospects soon join the MLB roster, it's fair to say that the Brewers are only going to get better over the next three to five years. Certainly the argument can be made that William Contreras likely has only one more season in Milwaukee and Brice Turang and Christian Yelich likely won't be on the roster in five years' time, but if there's a season to go "all-in" on, it might be next year or 2028, rather than this year.

Even still, MLB teams can't take for granted any season in which they are in contention. With the growing prevalence of pitching injuries, the uncertainty surrounding prospects, and an ever-changing league structure, it's difficult to justify not taking advantage of opportunities to make a deep postseason run when possible. Such a line of thinking brings up another question: "what do the Brewers actually need to do at the deadline to topple the mighty Dodgers, or the first-place Braves for that matter?"

It's a difficult question to answer at this juncture, especially because the Brewers have just thrown a wrench named Cooper Pratt into the equation. Should Pratt solve the Brewers' left side of the infield woes, Milwaukee is free to prioritize an addition to their pitching staff at the trade deadline. Obviously, an addition of top-trade target Tarik Skubal would give the Brewers one of the best trios of starting pitchers in all of baseball -- something that can lead to a deep postseason run on its own. However, even an acquisition of an All-Star pitcher like Joe Ryan of the Minnesota Twins rather than a Cy Young arm like Skubal, would give the Brewers a formidable rotation capable of competing with the Dodgers in a five- or seven-game series.

The Brewers didn't have a trio of starting pitchers at the level of Miz, Harrison, and a major trade deadline acquisition when they faced Los Angeles in the NLCS in either 2018 or 2025. And yet, it wasn't their pitching that was the problem last year, or in several of their other playoff appearances in between 2018 and 2025. Instead, it was an offense that was clearly built for the regular season, but not the postseason that stalled multiple Brewers playoff runs. That reality would lead fans to believe that a position player acquisition -- one who adds significant "pop" to the Brewers' lineup -- is really what Matt Arnold and company should be prioritizing at the deadline, especially given the fact that the 2026 team is once again lacking in the homerun department.

It's not yet obvious what the Brewers should prioritize at the deadline or what will be available -- both will become clearer as the trade deadline draws nearer. However, one thing is clear: if the Brewers want to dethrone the Dodgers, a significant trade acquisition prior to the deadline will likely be required. In the meantime, Milwaukee needs to decide whether or not 2026 is the year in which they go "all-in."

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