How One Postseason Blunder Pushed Milwaukee to Trade a Promising Outfielder in a Defining Brewers Moment .MH

For sports fans, Thanksgiving generally involves an afternoon on the couch watching a slate of football games that the NFL has put together. However, Turkey Day also serves as a notable checkpoint in the baseball world, as something of an introduction to the offseason. With MLB’s non-tender deadline occurring just before Thanksgiving and the Winter Meetings taking place shortly after, the harvest holiday is often accompanied by several baseball trades that can have a significant impact on the season ahead.

More common than trades taking place on the actual day are deals being agreed upon in the days leading up to Thanksgiving. This year, the New York Mets and Texas Rangers swapped veterans Brandon Nimmo and Marcus Semien, and the St. Louis Cardinals sent their ace, Sonny Gray, to the Boston Red Sox in exchange for two controllable arms. The Milwaukee Brewers, despite not being active during this year’s build-up to Turkey Day, are no stranger to the pre-Thanksgiving swap. The Hunter Renfroe salary dump took place two days before Thanksgiving back in 2022, but three years prior, an even more notable trade went down on the holiday’s eve.

November 27, 2019: Brewers trade OF Trent Grisham and RHP Zach Davies to San Diego Padres for INF Luis Urías and LHP Eric Lauer in four-player Thanksgiving eve swap

Though it was the day before Thanksgiving back in 2019, it was on this day six years ago that the Brewers parted ways with their talented young outfielder, Trent Grisham. Despite coming off an impressive rookie season in Milwaukee, Grisham was the owner of a brutal misplay during the Brewers’ 2019 Wild Card Game loss to the Washington Nationals, who went on to win the World Series that year.

With a two-run lead in the top of the bottom of the eighth inning and Josh Hader on the mound, Juan Soto came to the plate with two outs. The Nationals had loaded the bases on a series of lucky plays, including Michael Taylor getting a free base on a “hit-by-pitch” that didn’t hit him and Ryan Zimmerman reaching on a bloop single that shattered his bat. Soto lined a single to right field, that should have scored just one run, two at the most, had Grisham fielded it cleanly. However, the ball went under his glove, allowing all three runs to score and handing the Nationals a lead that they maintained through the final frame.

It’s the type of play that makes both an organization and the player involved want a fresh start to exorcise the demons that might linger if the player continues to don the same jersey. For the same reason, it wouldn’t be surprising if the Philadelphia Phillies found a trade partner for Orion Kerkering this offseason after his error ended the Phillies’ 2025 season in heartbreaking fashion.

However, back in 2019, it was Grisham who was in need of a fresh start, and the Brewers gave him just that. They sent the rookie outfielder to the San Diego Padres alongside starting pitcher Zach Davies in exchange for infield prospect Luis Urías and left-handed starter Eric Lauer on the day before Thanksgiving.

Both sides can easily find reasons to be thankful for the trade; Grisham was phenomenal for two seasons in San Diego before his offensive numbers fell off a cliff in 2022. However, after being traded to the New York Yankees alongside Soto two offseasons ago, Grisham posted the best season of his career in 2025 and subsequently accepted a $22.025 million qualifying offer to stay in New York for the 2026 campaign. Additionally, Zach Davies was one of the best pitchers in baseball during the shortened 2020 season, before the Padres packaged him, Owen Caissie, and several other prospects in a deal with the Chicago Cubs for Yu Darvish and Victor Caratini. In true AJ Preller, the wheeling and dealing head of San Diego’s front office, fashion, both players were traded before they reached free agency.

For Milwaukee, they got a few 3.0+ Wins Above Replacement (WAR) seasons out of Urías in 2021 and 2022, before they traded him to Boston for Bradley Blalock at the 2023 trade deadline. Blalock was involved in a trade package that netted the Brewers Nick Mears, and Urías rejoined the organization for a few weeks last September, playing a total of 13 games for the Triple-A Nashville Sounds.

Lauer, meanwhile, also had two strong seasons in 2021 and 2022 with a combined 3.47 ERA in 277.1 total innings pitched to prove it. He faltered in 2023 and was granted free agency at the completion of the season. However, Lauer joined the Toronto Blue Jays last year and played an important role in their AL pennant-winning season; he pitched 5.2 scoreless innings in the World Series.

The pre-Thanksgiving swap between the Brewers and Padres didn’t produce a clear lopsided winner. Rather, both teams benefitted from the deal in their own way, with the Padres needing an outfielder and the Brewers needing an infielder. It’s the type of win-win trade that you love to see during the time of year when gratitude is in the air.