The Milwaukee Brewers aren’t alone in building a roster in myriad ways, but as they head into the 2025 postseason, it’s notable how many key contributors were acquired via trade.
That includes catcher William Contreras, outfielder Christian Yelich, starting pitchers Quinn Priester and Freddy Peralta, closer Trevor Megill, third baseman Caleb Durbin, shortstop Joey Ortiz, first baseman Andrew Vaughn, outfielder Isaac Collins and others like Chad Patrick, Nick Mears, Jake Bauers and Grant Anderson.
Here’s the list of the 15 greatest trades in Brewers lore … and the five worst (year in parentheses accounts for next season of action):
1. A haul from Whitey Herzog (St. Louis, 1981)
Brewers receive Pete Vuckovich, Rollie Fingers and Ted Simmons for Dave LaPoint, David Green, Lary Sorensen and Sixto Lezcano
The Brewers were more than willing to engage with Cardinals GM Whitey Herzog, looking to wheel and deal at the 1980 Winter Meetings. It’s not as if the Brewers didn’t give anything up; Lezcano and Sorensen had been mainstays, and Green was a promising prospect. But the acquisition of future Cy Young winners Fingers and Vuckovich and a future Hall of Fame catcher were essential in Milwaukee’s first postseason trips in 1981 and 1982, breaking through after the franchise had finally achieved competitiveness in the late 1970s.
Fingers won both the Cy Young and MVP that first season and never suited up for the Cardinals. It’s on the short list of most important transactions in Wisconsin sports history.
2. Coop for Boomer (Boston, 1977)
Brewers receive Cecil Cooper for George Scott and Bernie Carbo
Scott was a popular player in Milwaukee and perennial Gold Glover, and he was an all-star again with Boston in 1977, but his best years were behind him. Cooper, meanwhile, became one of the greatest players in Brewers history, with five all-star appearances, a legendary moment in the 1982 playoffs, two Gold Gloves and three top-five finishes in the MVP voting.
3. CC Sabathia (Cleveland, 2008)
Brewers receive CC Sabathia for Matt LaPorta, Rob Bryson, Zach Jackson and Michael Brantley
We could hedge here and say the development of Michael Brantley into a star elsewhere negates the value of this trade, but nah. Sabathia was a revelation in the second half of the 2008 season, willing Milwaukee to its first playoff appearance in 26 years. Top prospect LaPorta didn’t pan out, and only Brantley would be a regrettable loss. Some of these trades are thefts based on value and some are just truly important because of their importance to the psyche of the fan base. Sabathia was just inducted into the Baseball Hall of Fame.
4. Thanks for the MVP (Miami, 2018)
Brewers receive Christian Yelich for Lewis Brinson, Isan Diaz, Monte Harrison and Jordan Yamamoto
The prospects never panned out for Miami, while Yelich had an MVP season in 2018, came close to another in 2019 and is one of the franchise’s cornerstones. Even though his production never matched those seasons, he’s rediscovered his magic in 2024 and 2025, getting 100 RBIs this season for the second time in his caerer.
Adding to the mystique around the deal was that it went down Jan. 25, 2018, the same day the Brewers signed Lorenzo Cain.
5. The last piece (Houston, 1982)
Brewers receive Don Sutton for Frank DiPino, Kevin Bass and Mike Madden
It’s arguably the most notable mid-season acquisition in Brewers history — well, second to Sabathia, probably — when Sutton was acquired in August and provided the veteran ammunition that helped the Brewers reach the World Series. These were the twilight years of Sutton’s Hall of Fame career, and Houston made out fine; all three players spent at least four years with the Astros. But the Brewers certainly got what they wanted out of the exchange.
6. Getting out of The Trop (Tampa Bay, 2021)
Brewers receive Willy Adames and Trevor Richards for J.P. Feyereisen and Drew Rasmussen
Adames’ arrival coincided with a personal and team-wide offensive awakening that made Milwaukee one of the top teams in baseball, and it didn’t stop in the short term. He was an offensive linchpin over the next three seasons, a starting shortstop for a team that made playoff appearances in 2021, 2023 and 2024 before he signed a monster free-agent deal with the San Francisco Giants. Adames hit 178 homers in Milwaukee with a .762 OPS and excellent defense for the vast majority of his run.
Richards was also effective as a relief pitcher before he was dealt again, this time for slugging first baseman Rowdy Tellez, another key addition to the 2021 team. Feyereisen continued to be effective but ran into injuries, and Rasmussen has developed into a valuable pitcher for the Rays, making his first all-star team in 2025 and owning a career 2.89 ERA in 128 games.
7. Getting something for (almost) nothing (Oakland and Atlanta, 2023)
Brewers receive William Contreras, Joel Payamps and Justin Yeager for Esteury Ruiz (to Oakland). Atlanta receives Sean Murphy. Oakland receives Manny Piña, Kyle Muller, Freddy Tarnok and Royber Salinas.
It seemed like a low price to pay, even at the time, and it has turned out to be an even greater bargain as the years passed. In a three-team offseason trade, the Brewers acquired promising Atlanta catcher Contreras, a recent all-star, and also got a quality reliever in Payamps purely for Ruiz, a speedy outfielder who’d been acquired the year before in the Josh Hader trade. Atlanta had its sights on bringing in a new catcher in Oakland’s Sean Murphy, making Contreras expendable, and the A’s apparently had their heart set on a number of guys.
In three years with the Brewers, all Contreras has done is start an All-Star Game, win two Silver Sluggers and collect MVP votes in 2023 and 2024, serving as a cornerstone on both sides of the ball. Ruiz hasn’t been able to latch on permanently in the big leagues.
8. Mr. Warmth heads north (Cincinnati, 1977)
Brewers receive Mike Caldwell for Dick O’Keefe and Garry Pyka
Caldwell bounced around in the late 1970s, with injuries limiting his output, but he became a centerpiece for Milwaukee, first as Cy Young runner-up in 1978 and then as the top starter on the 1982 American League champion. The two minor-leaguers for which he was traded never saw the big leagues.
9. A re-made roster for Richie Sexson (Arizona, 2004)
Brewers receive Chad Moeller, Chris Capuano, Craig Counsell, Jorge de la Rosa, Junior Spivey and Lyle Overbay for Richie Sexson, Shane Nance and Noochie Varner
The absolute haul for Sexson changed the complexion of the Brewers. Overbay became a popular player and doubles machine, Capuano became a reliable lefty starter who won 18 games one season and made the all-star team, Counsell’s tenure in Milwaukee included two playoff appearances as a player and three more playoff trips (and counting) as a manager. Sexson, meanwhile, played in only 23 games for the Diamondbacks before sustaining a season-ending injury, and he signed with Seattle for the following year.
10. Spider-Man for Slaton, temporarily (Detroit, 1978)
Brewers receive Ben Oglivie for Jim Slaton and Rich Folkers
Slaton won 17 games for the Tigers in 1978 but was back with the Brewers in 1979 and stayed another five seasons (he remains the franchise’s all-time leader in wins). Folkers never pitched in the big leagues again. Oglivie, meanwhile, became a staple over the final nine years of his career in Milwaukee, making three all-star teams and playing a vital role on the team’s 1982 World Series runner-up. He hit 41 homers and batted .304 in 1980.
11. Doug Melvin’s last gift (Houston, 2015)
Brewers receive Josh Hader, Adrian Houser, Domingo Santana and Brett Phillips for Carlos Gómez and Mike Fiers
One of Doug Melvin’s final moves as Brewers GM was a huge one, bringing in four young players who all developed for the Brewers in different ways. Santana contributed to the 2018 NL Central title, Phillips became part of a deal that brought 2018 playoff hero Mike Moustakas to Milwaukee, Houser was in the rotation for much of his five seasons and Hader became a dominant reliever with three all-star selections. The deal was also completed under strange circumstances, after a trade that would have sent Gómez to the Mets was nixed at the last minute. Gómez’s best days were behind him, and though Fiers threw a no-hitter for Houston later that year, Milwaukee would definitely make the trade again.
12. The lottery ticket pays off (Seattle, 2016)
Brewers receive Carlos Herrera, Daniel Missaki and Freddy Peralta for Adam Lind (Seattle, 2016)
The Brewers acquired three teenagers for Lind, a productive first baseman but not an essential keeper for a franchise that wasn’t winning games at the time. Peralta is the lottery ticket that hit big. The two-time all-star is about to become the first Brewers player to appear in six postseasons, emerging as a reliable arm over his eight seasons and arriving as a bona fide ace in 2025.
13. Shaw jewel (Boston, 2017)
Brewers receive Josh Pennington, Mauricio Dubón and Travis Shaw for Tyler Thornburg
Shaw became a linchpin in the 2017 and 2018 teams, while Thornburg’s injury troubles made him a non-factor for the Red Sox. Dubón was later traded for Drew Pomeranz, who became an essential component to Milwaukee’s 2019 playoff run, though Dubón remains a steady big-leaguer in 2025 with Houston.
14. Right on the Money (Philadelphia, 1973)
Brewers receive Bill Champion, Don Money, John Vukovich for Earl Stephenson, Jim Lonborg, Ken Brett, Ken Sanders
It cost the Brewers a lot, but they did get a four-time all-star in Money, a player who might just be the most underrated in Brewers history, given his excellence on both offense and defense. Brett, Lonborg and Sanders had a lot of tread left on the tires, but it’s again a trade Milwaukee would make again.
15. Feel the Burn (Cleveland, 1996)
Brewers receive Jeromy Burnitz for Kevin Seitzer
The popular slugger Burnitz spent six seasons in Milwaukee, including a 1999 season in which he started the All-Star Game. Seitzer only played in 22 games for Cleveland in 1996 and was out of baseball after the 1997 season.
Honorable-mention great Brewers trades
What about the most regrettable deals in Milwaukee history?
1. The Josh Hader trade (San Diego, 2022)
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. 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.
2. Loss of Cruz control (Texas, 2006)
Brewers receive Francisco Cordero, Kevin Mench, Laynce Nix and Julian Cordero for Carlos Lee and Nelson Cruz
Lee fared well in Texas but signed with Houston the year after that, and the Brewers got two good years out of Francisco Cordero at closer before he signed with Cincinnati. But most everyone remembers the other details: Nix and Mench didn’t pan out, and Nelson Cruz … well, became a superstar. It doesn’t matter how often you remind everyone that Cruz was later designated for assignment by the Rangers and could have been signed by anyone before re-upping in Texas; this remains a colossal “one-that-got-away” in Brewers lore.
3. The real Vaughn valley (San Diego, 1996)
Brewers receive Bryce Florie, Marc Newfield and Ron Villone for Greg Vaughn and Gerald Parent
The Brewers anticipated this was a bold rebuilding stroke when they moved their slugging outfielder at the deadline, but despite a great start from Newfield in that first half-season, he never developed into an everyday player. Villone and Florie were passable but didn’t stay long-term. Vaughn, meanwhile, went on to play seven more seasons, with two all-star appearances and two top-five finishes in the MVP voting.
4. Coors light (Colorado, 1993)
Brewers receive Kevin Reimer for Dante Bichette
Bichette had been a solid player in the second of his two Milwaukee seasons, but he flourished in the mountains, making four all-star teams over his next seven years with the Rockies. Reimer played one year in Milwaukee and was out of baseball thereafter.
5. A very early misfire (Houston, 1970)
Brewers receive cash for Mike Marshall
The 26-year-old floundered with the Seattle Pilots in 1969 and was moved to Houston, where things got no better in limited work. But he caught on when he was traded again to Montreal alter in the 1970 season. In 1972, his ERA was 1.78 and it marked the first of three straight years in which he finished top-five in the Cy Young voting (and top-10 in the MVP voting) In 1974, he spent the first of two all-star seasons with the Dodgers, posting a 2.42 ERA and winning the Cy Young. In all, he spent 14 seasons in MLB with nine teams.
High honorable mention: A farewell to Gorman (Cleveland, 1983)
Brewers receive Rick Manning and Rick Waits for Gorman Thomas, Ernie Camacho and Jamie Easterly
Gorman Thomas’s best days were behind him when the Brewers traded him to Cleveland, and though it can be argued as a net loss for the Brewers, it’s hardly a devastating failure on paper. But Thomas’s popularity was sky-high in Milwaukee, putting Manning behind the eight-ball even before he famously singled in a winning run with Paul Molitor’s 39-game hitting streak left to die on deck. its. Manning was unfairly vilified, but it’s definitely a trade people remember.
High honorable mention: An unhappy phenom (San Diego, 1992)
Brewers receive Jose Valentin, Matt Mieske and Ricky Bones for Gary Sheffield and Geoff Kellogg
It still has to be considered a bad one, since Sheffield went on to have a long and productive career that included eight all-star appearances. But he also was unhappy in Milwaukee, and the Brewers received three players who were regulars for much of the remaining decade.
Other rough trades in Brewers history
This article originally appeared on Milwaukee Journal Sentinel: These are the 15 best trades in Brewers history (and the five worst)
Reporting by JR Radcliffe, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel
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