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Brewers' 3 Keys to a Perfect 2026 Trade Deadline

Here's how Milwaukee can dominate...
Senior Vice President and General Manager Matt Arnold speaks during an an end of season press conference at American Family Field in Milwaukee, October 10, 2023.
Senior Vice President and General Manager Matt Arnold speaks during an an end of season press conference at American Family Field in Milwaukee, October 10, 2023. | Mike De Sisti / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

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The Milwaukee Brewers win games every year by being one of the smartest organizations in Major League Baseball. This year, they have to set their aspirationss higher than ever.

With a commanding 5 1/2-game lead in the National League Central as of Saturday, the Brewers look like a top World Series contender for the second straight season. The whole league is chasing the two-time defending champion Los Angeles Dodgers, so the trade deadline will be an important time for Milwaukee to cash in where it can.

Knowing that the Brewers have a great farm system, but can't necessarily compete with the Dodgers or New York Yankees in terms of adding payroll, here are some overarching objectives that the Brewers need to make sure their deadline addresses.

Leave deadline with left side of infield solved

Cooper Pratt
Jun 19, 2026; Cumberland, Georgia, USA; Milwaukee Brewers shortstop Cooper Pratt (12) fields the ball against the Atlanta Braves during the second inning at Truist Park. Mandatory Credit: Jordan Godfree-Imagn Images | Jordan Godfree-Imagn Images

Brewers fans are painfully aware that their shortstops and third basemen have combined for some of the worst numbers at those positions in the game this season. Fortunately, trading for upgrades at those positions is an option, but not yet a mandate.

Calling up top prospect Cooper Pratt and cutting ties with bust free agent signing Luis Rengifo was the most obvious move the Brewers could make to switch things up. There's another top prospect in Jett Williams who could be part of the solution. But the next month and a half needs to be enough time for the Brewers to decide whether another supporting cast member is required.

Don't get complacent with pitching staff

Misiorowski
Jun 19, 2026; Cumberland, Georgia, USA; Milwaukee Brewers pitcher Jacob Misiorowski (32) pitches against the Atlanta Braves during the second inning at Truist Park. Mandatory Credit: Jordan Godfree-Imagn Images | Jordan Godfree-Imagn Images

We know pitching is one of the Brewers' biggest strengths, and this season, Jacob Misiorowski and Kyle Harrison are combining to lead the pitching staff with 15 more strikeouts than any other team (as of Saturday). But there's more to be had here.

Whether it's another starter to form a three-headed monster heading into the playoffs or some added security at the back end of the bullpen, the Brewers can't alow good to become the enemy of great when it comes to shopping for pitching upgrades.

Find some 'it factor'

Consider this agenda item solved if the Brewers leave the deadline with current Detroit Tigers ace Tarik Skubal. But even if we acknowledge that such a scenario is fairly unlikely, there's still a need to add some je ne sais quoi to this Milwaukee roster.

Maybe it's added home run power to get the Brewers out of the basement in the slugging stat categories. Maybe it's a veteran bat who bring some rallying cries to the locker room. Maybe it's even a lockdown reliever who has wild celebrations when he gets out of jams. It just feels like this Brewers team, solid as it is, is missing some it factor.

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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