3 unanswered questions that will shape Brewers' 2026 trade deadline strategy

One of the biggest challenges at Major League Baseball's trade deadline is trying to predict future performance. While fans often clamor for blockbuster acquisitions, the Milwaukee Brewers have frequently opted for more measured moves, recognizing that even the biggest deadline deals don't always produce the expected results.

A prime example came last season, when Eugenio Suárez struggled after being acquired by the Seattle Mariners, batting below .200 with a .255 on-base percentage despite arriving as one of the deadline's premier offensive additions. Meanwhile, Milwaukee got great production out of Brandon Lockridge, who was forced into a more prominent role when the Brewers lost Jackson Chourio for the month of August due to a hamstring strain.

Another aspect that factors into the equation of which positions and players to target at the trade deadline is predicting future outcomes from players currently on the team. Here, we take a look at three of those unanswered questions that will shape the Brewers' deadline decisions.

3 unanswered questions that will shape Milwaukee Brewers' 2026 trade deadline strategy

1. Who would be the Brewers' No. 3 starting pitcher in a playoff series?

With the Brewers already adding pitching depth in Lance McCullers Jr. and Colton Gordon, the front office appears to recognize that Misiorowski and Harrison both may need to be slowed down in the second half. Doing so will hopefully allow them to be healthy and at their peak come the postseason, when the duo on top of their rotation will be needed the most.

With Brandon Woodruff officially out for the rest of the 2026 season, the focus shifts to another critical question: Who would be the Brewers' No. 3 starter in a postseason series? If Milwaukee believes one of Brandon Sproat, Shane Drohan, Logan Henderson, Robert Gasser, McCullers Jr., or Gordon can capably fill that role, then another rotation addition may not be necessary. If there are doubts about any of those internal options, however, the Brewers should strongly consider acquiring another starting pitcher before the Aug. 3 trade deadline.

2. Can Joey Ortiz's offensive improvement be trusted?

Third base has been one of Milwaukee's biggest question marks all season. Luis Rengifo failed to solidify the position, leaving the Brewers to rely on a platoon of David Hamilton, who is currently sidelined with a hamstring strain, and Joey Ortiz. While Ortiz struggled offensively for much of the season, particularly when he was playing shortstop regularly, he has caught fire in July. Over his last 15 games, Ortiz is slashing .304/.347/.500, giving the Brewers reason to believe he may finally be turning the corner.

That said, Ortiz's overall track record as a hitter still leaves room for skepticism. Whether the Brewers believe his recent surge is sustainable could play a significant role in shaping their trade deadline plans. Complicating matters further is the presence of Jett Williams, who was reportedly in line for a promotion before a wrist injury delayed his major league debut. If Milwaukee believes Ortiz and Williams can provide enough production internally, they may stand pat. If not, adding an external option at third base could remain on the table over the next few weeks.

3. How big of an impact will DL Hall have once he returns from injury?

Before landing on the injured list in early June with a pectoral strain, DL Hall was enjoying the best season of his career. The left-hander posted a 2.03 ERA across 24 appearances and 31.0 innings, building on a strong 2025 campaign in which he recorded a 3.49 ERA in limited action. Hall is expected to begin a minor league rehab assignment soon before rejoining Milwaukee's bullpen, where he would provide the Brewers with another valuable left-handed relief option.

There's no doubt Hall's ability to cover multiple innings will provide a significant boost for Milwaukee once he returns. His versatility could also help ease some of the workload on Aaron Ashby during the second half. The bigger question, however, is whether Hall can work his way into the Brewers' postseason plans, as he has yet to make an October appearance for the organization.

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