The Milwaukee Brewers find themselves in familiar territory heading into the 2026 All-Star break. The Crew is comfortably in first place in the NL Central division, and their sights are set on a deep October run.
After qualifying for the postseason in six of the last seven years, the Brewers are used to being “buyers” at the trade deadline, which is August 4th this season. They have historically sought bullpen help in July, most notably acquiring Shelby Miller, Jordan Montgomery, and Nick Mears in the last two seasons. While that trio did not make Milwaukee an instant title contender, the Brewers now have upgraded bargaining chips to dangle that were not available previously.
Unlike past seasons, Milwaukee can no longer be satisfied with another divisional title, and grabbing “guys” to fill roster spots is unacceptable. Just being “happy to be there” in the playoffs is no longer enough: It is time to gamble and sell out for a World Series championship. Here are the areas the Brewers must target and who may be used as bait to secure them.
On paper, Milwaukee’s bullpen has been an area of strength in 2026. Aaron Ashby leads all of MLB with 12 wins, and after uneven starts to the season, Abner Uribe and Trevor Megill are now solid in the back end of games. Beyond that, however, the relief corps has been serviceable but unpredictable when called upon.
Grant Anderson has not proven to be a high-leverage guy. Shane Drohan has pitched well out of the bullpen, but he is making a strong case to stay in the starting rotation. DL Hall flashed moments of brilliance, but, once again, he is currently injured. Jared Koenig returned to the Brewers recently, but his velocity is not where it had been. Craig Yoho is not consistent enough to be trusted at the major league level, and Joel Kuhnel’s recent performance has proved to be troublesome.
With that said, who is being dangled for Milwaukee to shop for? The biggest name rumored to be on the move is Boston Red Sox closer and eight-time All-Star, Aroldis Chapman. The Red Sox are languishing this season, and at present, they stand at 41-48 in the NL East.
Zachary D. Rymer of Bleacher Report believes a union of Chapman and the Brewers remains likely, but it could cost Milwaukee a coveted minor-league prospect.
“As much as the Brewers could use another bat, their best route to the World Series is to go all-in on run prevention. Their bullpen could use another power arm, and Chapman is the best there is despite a couple recent stumbles,” Rymer wrote. “The Brewers’ No. 3 farm system should make them equal to the task, and one wonders if an MLB-ready catcher like Jeferson Quero could interest Boston.”
Jackson Roberts of si.com posited that Pete Fairbanks of the Miami Marlins is a viable option to shore up Milwaukee’s bullpen.
“(Trading for Fairbanks) would be a chance for the Brewers to grab another reliable righty, potentially even another ninth-inning option,” he wrote. “The Marlins could act like the responsible small-market team and play the long game for prospect talent.
Fairbanks fits Milwaukee because he gives Pat Murphy another swing-and-miss reliever capable of shortening postseason games against elite National League offenses.
With their recent stretch of stellar play, however, the Miami Marlins may be less inclined to sell their closer, who has recorded 12 saves this season. Miami has been the hottest team in all of baseball, going 24-8 since June 1. With their playoff chances enhanced, the asking price for Fairbanks may be true rich for the Brewers.
One darkhorse in the running could be Colorado Rockies‘ reliever Antonio Sentzatela. His team is falling off from the wild card race, and he could help in the middle or late innings. Sentzatela owns three saves and an 8-0 record in 27 appearances to go with a 2.93 ERA and 1.14 WHIP.
MLB insider Robert Murray of Fansided.com would be “surprised” if Milwaukee doesn’t trade for two positions this summer: starting pitcher and maybe even a hitter. Although the Brewers own the second-best record in MLB, they would be foolish not to pursue a thumping bat to add to their offense.
Matt Sullivan of the Sporting News feels there are plenty of solid possibilities to fulfill that desire.
“The mention of “another bat” is a lot more open-ended, but Milwaukee could end up upgrading the infield or the outfield with a move,” writes Sullivan. “There are plenty of options, including Luis Arraez, Willson Contreras, and Matt Chapman, who could work.”
Arraez and Chapman are presently playing for the San Francisco Giants, who 21.5 games out of first place in the NL West. Contreras, who would theoretically be teamed with brother William on the Brewers, is on the Red Sox.
Chapman would be the most inviting move for Milwaukee. The third-baseman could fill the power void at that position, currently manned by able defenders but marginal sluggers David Hamilton and Joey Ortiz. The Brewers and San Francisco, however, would have to be creative to make the swap.
Chapman and his agent negotiated a full no-trade clause. That means the Giants must get Chapman on board with a trade before they make it. If he wants to stay, then he stays.
Another hurdle to maneuver is Chapman’s vast contract. After the 2024 season, San Francisco signed Chapman to a six-year, $151 million deal, which means he is under control, to the tune of about another $100 million, until 2030.
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The Brew Crew has routinely become a championship contender. They are mentioned in the same conversations as the Los Angeles Dodgers and New York Yankees when discussing the short list of those who could potentially win it all.
Picking up proven stars like the two Chapmans would be atypical of how the economically-conscious Brewers have operated. On paper, the contracts they would have to absorb seem out of Milwaukee’s price range.
If the Brewers want to be invited to the adult table, they must put their money where their mouths are. As they say in Las Vegas, “the price of poker has just gone up.” To give their loyal fans something to yell about in October, risks must be taken and the status quo must be ignored. Staying on their current thrifty course has not worked in the playoffs before, and it is time to push all their chips into the middle.
Milwaukee has one of baseball’s deepest farm systems, a legitimate chance to win the National League, and several clear deadline needs. Standing pat, despite their lofty spot in the standings, would waste one of the best championship opportunities this franchise has ever had.
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