The Milwaukee Brewers have spent the first 103 games of 2026 piling up wins at a pace that has already pushed them to a franchise-best 64 victories. That’s three more than they had at the same point last year, even though the road to get there looked very different.
This season’s club has been steady almost from the jump, with the lone real stumble coming during a six-game losing streak in April. The 2025 team, by contrast, had to claw its way out of a sluggish start. It was 25-28 on May 24 before an eight-game winning streak helped flip the season, and by the time the trade deadline arrived, Milwaukee owned an MLB-best 64-44 record.
That strong position last summer gave the front office room to stay cautious. The Brewers had already gotten a major boost from Andrew Vaughn, acquired from the Chicago White Sox in exchange for Aaron Civale on June 13.
Vaughn didn’t actually make his Brewers debut until July 7, after Rhys Hoskins’ thumb injury opened the door, but once he got in the lineup he became a key piece. From July 7 through the end of the regular season, he hit .308/.375/.493 with nine homers, 14 doubles and 46 RBI in 64 games.
With Vaughn producing and the pitching staff stocked with veteran arms, Milwaukee didn’t have many obvious holes to fill at the deadline. The result was a restrained approach: a backup catcher, a depth outfielder and a promising reliever who was injured and never became available in the postseason.
A year later, the return on those moves looks mixed at best. Jansen got off to a slow start in August, but he finished well enough to post 0.7 bWAR in 25 games with the Brewers.
Jadher Areinamo, meanwhile, has not taken off in the Rays’ system; his strikeout rate has climbed while his walk rate has dropped. With Jansen never appearing in a postseason game and Areinamo’s future in Tampa Bay looking uncertain, that deal amounts to a wash.
The trade with the D-Backs has aged even more awkwardly. Montgomery was done for the season and later did not resign with the Brewers in free agency.
Miller, the centerpiece of the return, suffered a season-ending elbow injury in early September and also never got into a playoff game. Milwaukee took a financial hit, though not a crippling one, which leaves that swap in the same “wash” category.
The Padres deal looks better on paper, but only to a point. Lockridge has produced 0.8 bWAR in 48 games with the Brewers, while Cortes managed 0.0 bWAR in six rough starts for San Diego last year and Quintana has struggled in High-A this season. Even so, Lockridge is basically Milwaukee’s fifth outfield option now, and he didn’t matter in the postseason a year ago.
Put together, the 2025 deadline was a disappointment. Outside of Vaughn, who hardly fits the mold of a classic deadline swing, Milwaukee didn’t add a player who changed the postseason picture. For a team sitting atop baseball’s standings and armed with a deep farm system, that wasn’t enough.
The lesson is clear enough: the Brewers need bigger swings this time around. Depth is not the issue.
They already have enough serviceable pieces to patch holes if needed. What they need are players who can actually move the needle in October and give them a real shot at knocking off the Los Angeles Dodgers.
If there’s a blueprint, it’s 2018. That was Milwaukee’s most successful postseason run in this stretch, and it also happened to be the club’s most aggressive deadline. If the Brewers want to chase the National League pennant in 2026, another cautious deadline won’t get it done.
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Brewers Make Early Roster Shakeup That Could Hint At Deadline Plans
The Brewers made a quick roster adjustment Tuesday, reinstating David Hamilton from the 10-day injured list and clearing a spot by designating Braden Shewmake for assignment. It is the kind of small transaction that can look routine on the surface, but in Milwaukee it also fits into the larger roster puzzle as the club tries to keep its infield depth intact while preserving flexibility for the weeks ahead.
Shewmake, who arrived from the Houston Astros before the All-Star break, got a brief look with the Brewers and showed the sort of versatility teams value when injuries start to stack up. If he gets through waivers, Milwaukee could keep him in the organization by sending him to Triple-A, a possibility that would leave the front office with one more layer of depth as it weighs deadline moves and eventual returns from the injured list. [Read more 🡒]
Trevor Megill Had The Perfect Response To Brewers Trade Buzz
The Brewers are shaping up to be one of the more interesting teams to watch as the trade deadline approaches, with Matt Arnold and the front office expected to take a more aggressive swing than they have in past years. Milwaukee has been linked to help both in the rotation and in the bullpen, and the expectation around the industry is that at least one reliever could be added as the club looks to sharpen the roster for the stretch run.
For Trevor Megill, none of that appears to be rattling the day-to-day job. He has settled in as Milwaukees clear-cut closer after Abner Uribe briefly handled the role earlier this season, and his focus remains on the ninth inning rather than the rumor mill. Still, with the Brewers likely to make bullpen changes before the deadline passes, Megill knows a new face could be walking into the clubhouse soon enough. [Read more 🡒]
Brewers Are Circling Detroits Ace And Tigers Fans Know What That Means
The Brewers are already being linked to a more aggressive posture for the 2026 trade deadline, and the early buzz says they are not waiting around to see how the market develops. Milwaukee has talked with Detroit and San Diego about pitching help, a sign the front office is at least exploring the kind of swing that can change a postseason race rather than just patch a hole.
Tarik Skubal sits at the center of the conversation because a pitcher of his caliber would instantly reshape a rotation that has been thinned by injuries. Detroit would not move an arm like that cheaply, and the asking price figures to start with controllable starting pitching plus more beyond it, which is why this feels less like a rumor mill item and more like the beginning of a real test for Milwaukees willingness to pay up. [Read more 🡒]