May 24, 2023; Washington, District of Columbia, USA; San Diego Padres hats in the dugout during the game against the Washington Nationals at Nationals Park. Mandatory Credit: Brad Mills-Imagn Images Brad Mills-Imagn Images

Brewers-Padres Swap Called Worst Trade In Milwaukee History

Originally posted on Milwaukee Brewers on SI
By Patrick McAvoy | Last updated Sep 25, 2025 1:03 PM ET

The Milwaukee Brewers' front office clearly knows what it's doing. Milwaukee is in the middle of its best stretch of baseball in team history and just won the National League Central for the third straight season.

Despite this fact, even the Brewers haven't hit home runs on every move it has made. For example, JR Radcliffe of the Milwaukee Journal Sentinel made a list of the 15 best trades in team history and five worst. When it comes to the worst one, fans will certainly remember this one. Radcliffe had the San Diego Padres-Josh Hader deal as the worst one for Milwaukee.

The Brewers and Padres deal has been negatively received

"Brewers receive Taylor Rogers, Dinelson Lamet, Robert Gasser and Esteury Ruiz for Josh Hader
There are ways to argue that this can't possibly be the worst trade in franchise history; after all, Robert Gasser had a remarkable start to his career and could be a pivotal piece in the postseason," Radcliffe said. "Hader wasn't having his usual superb season. And Esteury Ruiz wound up being the Brewers' offering in one of the best trades on the above list. But this exchange is certainly the most notorious. Making the extraordinary step to deal an all-star as a first-place team, Brewers general manager David Stearns looked for long-term stability and, infamously, giving his team as many 'bites of the apple' as possible.

"The maneuver was seemingly unpopular in the locker room, and the Brewers dropped like an anchor out of first place to miss the playoffs — still the only postseason they've missed since 2017. The club immediately dropped Lamet, Rogers was ineffective the rest of that season, Ruiz was a project that still hasn't developed in the big leagues, and Gasser wound up needing Tommy John surgery after five excellent starts in 2023."

This deal shook up Milwaukee at the time. The actual idea of trading Hader wasn't bad. But, the timing of the deal was what shook up the fanbase. Plus, since then the return hasn't been great. This deal was a massive story at the time and even all of these years later can still upset fans. The Brewers have been fortunate since to have Devin Williams and Trevor Megill, but this deal really impacted the fanbase at the time.

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This article first appeared on Milwaukee Brewers on SI and was syndicated with permission.

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