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3 Biggest Questions Brewers Face As Trade Season Approaches

It's a good team. How much better can it get?
May 18, 2026; Chicago, Illinois, USA; Milwaukee Brewers third baseman Luis Rengifo (13) hits a single against the Chicago Cubs during the seventh inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images
May 18, 2026; Chicago, Illinois, USA; Milwaukee Brewers third baseman Luis Rengifo (13) hits a single against the Chicago Cubs during the seventh inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

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The trade deadline is a pivotal inflection point in many Major League Baseball teams’ seasons, and the Milwaukee Brewers are one of the teams with the biggest range of potential outcomes.

With a loaded farm system and pressure to deliver a long-awaited championship after consistently stalling out in the playoffs this decade, the Brewers might finally have incentive to make some blockbuster acquisitions this year. Then again, they’re the Brewers, which means they typically take the long-term approach and hang onto their prospects. Heck, sometimes they’ve even traded stars away when they were in playoff position.

As the trade rumor mill begins to heat up with the weather, the Brewers have a lot to ponder. Let’s run through some of the biggest questions they’re facing, and why there aren’t obvious answers just yet. 

Who plays third base and shortstop for rest of season? 

Ortiz
Jun 7, 2026; Denver, Colorado, USA; Milwaukee Brewers infielder Joey Ortiz (3) turns a double play ahead of a slide by Colorado Rockies infielder Kyle Karros (12) in the fourth inning at Coors Field. Mandatory Credit: Christopher Hanewinckel-Imagn Images | Christopher Hanewinckel-Imagn Images

It’s been the question looming over the Brewers’ heads all year. Joey Ortiz and David Hamilton are no one’s idea of a formidable shortstop platoon, and Luis Rengifo has been one of the worst value free-agent signings of the year. Either third base, shortstop, or both could be turned over to new players soon.

But will the Brewers go after a veteran on the trade market to replace one or two of those guys? Or will they simply entrust the role(s) to top prospects Cooper Pratt and/or Jett Williams, who are both knocking on the door at Triple-A Nashville.

Does Brewers bullpen get a new closer?

Between Abner Uribe and Trevor Megill, the Brewers certainly have capable closers. But one could argue that to make this team as fearsome as possible by playoff time, a more prolific ninth-inning man could be a difference-maker. 

We’ve seen lots of contending teams go after the biggest fish in the relief market and wind up successful in recent years, even when it seemed like guys like Mason Miller and Jhoan Duran might not be moved. This season, Aroldis Chapman is most obvious prospective closer target, but maybe there will even be other names for the Brewers to ponder.

Assuming no Tarik Skubal, which stars are possible targets?

Peralta
May 23, 2026; Miami, Florida, USA; New York Mets starting pitcher Freddy Peralta (51) reacts against the Miami Marlins during the fifth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | Sam Navarro-Imagn Images

Most Brewers fans would likely love to see their favorite team take a swing at landing the consensus best pitcher in the sport, even if it’s almost assuredly for two months before he signs a massive deal in a bigger market. 

It would be hilarious to see the Brewers go after Freddy Peralta only six months after trading him for two Top 100 prospects, but there are other starting pitchers to be had. Or maybe the Brewers find a way to pry Zach Neto loose from the rudderless Los Angeles Angels. Whoever it might be, the biggest fish the Brewers chase will tell us a lot about how serious this team is about going all the way. 

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Milwaukee Brewers On SI please reach out to Scott Neville: scott@moreviewsmedia.com