5 of the best trades in Brewers history, 5 of the worst

The MLB trade deadline isn’t until the end of next month, but it’s always a good time to look back at some of the best and worst trades in Milwaukee Brewers’ franchise history. The Brewers have generally done quite well in the trade market; many of the best players in franchise history were acquired through trade after they had already debuted in the big leagues, and there are no “Jeff Bagwell for Larry Andersen” mistakes on their record. Let’s take a look at what we feel are the five best and five worst trades in team history, plus a couple of extra more complicated ones.  

The 5 best trades in Brewers history

5. December 12, 2022: William Contreras

Full trade: Milwaukee sends Esteury Ruiz to Oakland; Oakland sends Sean Murphy to Atlanta and Joel Payamps to Milwaukee; Atlanta sends Royber Salinas, Kyle Muller, Manny Piña, and Freddy Tarnok to Oakland and William Contreras and Justin Yeager to Milwaukee

In a move that surprised people even at the time, the Brewers snuck into the blockbuster trade between Oakland and Atlanta that sent Murphy to the Braves. All the Brewers sent out was the speedy prospect Ruiz, and in return, the Brewers got Contreras from Atlanta and Payamps from Oakland. Payamps was a big part of the Brewers’ division-winning bullpen in 2023 and 2024, but Contreras is the obvious gem; he’s been better than Murphy since the trade, got MVP votes in both 2023 and 2024, and won Silver Sluggers both seasons. Ruiz led the AL in steals in 2023 but was demoted early in 2024 and now plays in the Dodgers’ minor league system.

4. July 7, 2008: CC Sabathia

Full trade: Milwaukee sends Matt LaPorta, Rob Bryson, Zach Jackson, and a PTBNL (Michael Brantley) to Cleveland for CC Sabathia

This one is a bit complicated by the fact that one of the pieces Milwaukee sent to Cleveland turned out to really be something; Brantley, who was the player-to-be-named-later, ended up having an excellent career. But the Sabathia trade is an integral part of Brewers lore. He had one of the most electrifying half-seasons in the history of baseball and essentially single-handedly led the Brewers to their first postseason appearance in 26 years, ending a quarter-century of ineptitude and setting the franchise on a path of success that continues to this day. Yes, Brantley turned into a stud, but no Brewer fan would ever go back on this trade.

3. December 6, 1976: Cecil Cooper

Full trade: Milwaukee sends Bernie Carbo and George Scott to Boston for Cecil Cooper

Milwaukee fleeced Boston for a star first baseman twice in the 1970s; in this trade’s prequel, Milwaukee acquired Scott from the Red Sox in 1971. He had five great years in Milwaukee and was the nascent franchise’s first major star. But by the end of the 1976 season, Scott was soon-to-be 33, and the Brewers decided to move on… by sending him back to Boston, along with outfielder Bernie Carbo, for another young first baseman: Cecil Cooper. Coop showed some real promise with the Red Sox but couldn’t get a consistent role; in Milwaukee, he became a star. He spent 11 years in Milwaukee and for a five-year run from 1979-83, he was a legitimate MVP candidate. Ultimately, Cooper earned over 30 WAR as a Brewer and is one of the best players in their history.

2. December 12, 1980: Rollie Fingers, Ted Simmons, and Pete Vuckovich

Full trade: Milwaukee sends David Green, Dave LaPoint, Sixto Lezcano, and Lary Sorensen to St. Louis for Rollie Fingers, Ted Simmons, and Pete Vuckovich

Milwaukee had to part with some real talent to complete this swap with the Cardinals, as Sorensen still had one good year in him, and Lezcano, who’d been a star with the Brewers, had one more excellent year in 1983 (though not in St. Louis). But the players they received had unprecedented success over the next couple of seasons: Fingers won the Cy Young and MVP in 1981, and Vuckovich won the Cy Young in 1982 (even if it was a dubious victory), and Fingers and Simmons ended up in the Hall of Fame.

But the biggest thing was the addition of some veteran presence to a talented but inexperienced team. Milwaukee had multiple 90-win seasons in the late 1970s but never reached the postseason; in 1981, behind Fingers’ monster season, they made the playoffs for the first time, and the following year they won what is still the only pennant in team history. That’s the legacy of this trade, and while you could quibble with some of the individual numbers (which aren’t as good as some remember), the impact is clear.

1. January 25, 2018: Christian Yelich

Full trade: Milwaukee sends Lewis Brinson, Isan Diáz, Monte Harrison, and Jordan Yamamoto to Miami for Christian Yelich

Yelich had been a good player in Miami, but immediately upon his arrival in Milwaukee, he accessed power that he’d never had before, and he won the MVP in 2018 and probably would have again in 2019 if not for an injury that cost him the final month of the season. It has been up and down since, but Yelich has earned over 25 WAR as a Brewer and is one of the best players in team history, and the team’s longest sustained period of success coincides with his arrival. None of the four prospects that Milwaukee sent to the Marlins amounted to anything; in fact, the combined value of their major league careers is negative seven WAR.

Honorable mentions for best trade: Brewers get John Briggs for essentially nothing (April 1971); the giant trade that brought in George Scott (October 1971); the giant trade that brought in Don Money (October 1972); the Ben Oglivie acquisition (December 1977); getting Jeromy Burnitz for nearly-done Kevin Seitzer (August 1996); getting Willy Adames for oft-injured Drew Rasmussen and JP Feyereisen (May 2021)

The 5 worst trades in Brewers history

5. July 31, 1996: Greg Vaughn

Full trade: Milwaukee sends Greg Vaughn and Jerry Parent to San Diego for Bryce Florie, Marc Newfield, and Ron Villone

This is complicated by the fact that Vaughn, who was probably the Brewers’ best player in the first half of the 1990s, was approaching free agency. He was off to his best start in 1996 and had already hit a career-high 31 homers by the trade deadline; he finished with 41 homers. He stayed with San Diego as a free agent, and after a poor, injury-plagued season in 1997, he hit 50 bombs in 1998 and finished fourth in MVP voting for a pennant-winning Padres team. They traded him to Cincinnati before the 1999 season, and he hit 45 more homers.

The supposed prize of the Padres’ package was Newfield, the sixth overall pick in 1990, who was still young and had been a major prospect. He had a nice start with the Brewers but diminished quickly and was out of the league after the 1998 season.

4. January 12, 2000: José Valentín

Full trade: Milwaukee sends Cal Eldred and José Valentín to Chicago White Sox for Jaime Navarro and John Snyder

Valentín had been Milwaukee’s starting shortstop since 1994—he was a nice defensive player who could hit with some power, and he peaked as a Brewer in 1996 when he hit 24 homers, knocked in 94 runs, played good defense, and earned 3.9 WAR. But he was bad in 1999, and with one year of team control remaining, Milwaukee shipped him out. Eldred, a bit of a team legend for his early-90s exploits, was battling injuries by this point in his career and hadn’t been good for a while.

The return was a complete bust: Navarro, who’d had some good years in Milwaukee in the early 1990s, was completely washed up (he made only 12 more appearances in his career), and Snyder made 23 bad starts for the 2000 Brewers and never pitched in the majors again.

Valentín, meanwhile, hit a new gear in Chicago. The reasoning behind trading him wasn’t unsound, but Valentín—who’d never had an OPS+ above 90 in a full season—became a good offensive player in Chicago and continued playing excellent defense. Over the next five years on the South Side (he re-upped as a free agent after the 2000 season), Valentín averaged 3.4 WAR and 27 home runs per season.

Eldred also had a pretty good year for Chicago in 2000 before injuries cost him essentially the next two seasons. He had a final chapter as a useful reliever for three seasons in St. Louis from 2003-05 before retiring.

3. August 20, 1977: The Gorman Thomas Near-Miss

Full trade: Milwaukee sends a PTBNL (Gorman Thomas) to Texas for Ed Kirkpatrick

This didn’t end up hurting Milwaukee, but it needs to be included because of how close it was to being a disaster. The Brewers acquired Kirkpatrick for the last month of the 1977 season. He never played in the big leagues again after the 29 games he played in Milwaukee. To complete that deal, Milwaukee sent 25-year-old Gorman Thomas to the Rangers after the season.

Thomas had played parts of four seasons with the Brewers and, to be fair, they hadn’t gone well. But he spent his entire age-26 season in 1977 at Triple-A Spokane and tore through the Pacific Coast League: he hit .322/.436/.640 with 41 doubles, 36 homers, and 20 stolen bases. Still, Milwaukee must have decided he was a “4-A” player, and he was sent along to Texas.

Luckily, they experienced some buyer’s remorse and reacquired him just before spring training, so Thomas never played a game in the Rangers’ system. He broke camp with the Brewers in 1978, and over the next five years, he hit 175 homers, earned at least 3 WAR every season, led the league in homers twice, and got MVP votes twice.

This was very nearly a complete disaster.

2. July 28, 2006: Nelson Cruz

Full trade: Milwaukee sends Nelson Cruz and Carlos Lee to Texas for Julian Cordero, Francisco Cordero, Kevin Mench, and Laynce Nix

This one is complicated. Cruz earned over 40 WAR and hit 464 home runs after the Brewers traded him away, but there are two things that temper that: first is that he eventually served a steroid suspension, and second is that he was a late bloomer; Cruz spent eight years in Texas, but his best seasons came later, in Baltimore, Seattle, and Minnesota when he was in his mid-to-late 30s. So, even if the Brewers hadn’t traded him, those good years would probably have still come for another team.

Lee was also a star, and he had a couple more good seasons, but he was approaching free agency at the time of the trade, and it was clear Milwaukee would not be resigning him.

Francisco Cordero made the All-Star Game in 2007 and had a good year-and-a-half run as Milwaukee’s closer before leaving in free agency. None of the other players Milwaukee got in this group amounted to much, though.

1. December 6, 1976: Darrell Porter

Full trade: Milwaukee sends Darrell Porter and Jim Colborn to Kansas City for Jamie Quirk, Jim Wohlford, and a PTBNL (Bob McClure)

Porter had been the fourth overall pick in 1970, debuted at 19 in 1971, and finished third in Rookie of the Year voting in 1973. He was Milwaukee’s starting catcher from 1973-76, and was quite good for the first three of those years, but he was a player who hit for low averages whose greatest strength was his ability to take a walk, an underappreciated skill at the time. He had a bad season in 1976, and even though he was only 24, Milwaukee decided to ship him to the Royals.

In Kansas City, Porter regained his form in 1977 and 1978 before having one of the best seasons ever by a catcher in 1979: he hit .291 with 10 triples, 20 homers, and a major league-leading 121 walks. He earned 7.6 WAR, tied for the sixth-most ever by a catcher in a single season. He joined the Cardinals in 1981 and was St. Louis’s starting catcher in the 1982 World Series… in which they defeated the Brewers. He finished his career with 40.8 WAR, 29.7 of which came after the Brewers traded him, and while he’s not quite a Hall of Fame candidate, he’s probably within the top 30 catchers of all time.

As an added insult, Colborn—a former Brewer All-Star—had one of his best years with the Royals in 1977. Quirk and Wohlford bombed spectacularly, even though both managed long (ineffective) careers. McClure was the only player who offered any value to Milwaukee, for whom he pitched ten seasons in various roles with varying levels of success.

Dishonorable mentions for worst trade: Jeff Cirillo and Scott Karl to Colorado for Jamey Wright, Henry Blanco, and Jimmy Haynes (December 1999); Mark Loretta to Houston for Wayne Franklin and Keith Ginter (August 2002); Khris Davis to Oakland for Bubba Derby and Jacob Nottingham (February 2016)

Finally, a few complicated ones

Milwaukee trading Gary Sheffield before the 1992 season is, on paper, the best player the Brewers ever sent out. But things were a mess with Sheffield, and it was never going to work in Milwaukee, and they did acquire some actual contributors (Ricky Bones, Valentín) in return.

The 2010 Zack Greinke trade is tricky, because it only kind of worked for the Brewers—Greinke was just “fine” in 2011, even as Milwaukee won the division, and the team wasn’t in a place to keep him beyond the 2012 trade deadline as he approached free agency. The players Milwaukee sent out—Lorenzo Cain, Alcides Escobar, Jake Odorizzi, and Jeremy Jeffress—were all solid (or better, in Cain’s case) major leaguers, two of whom, Cain and Escobar, played major roles on back-to-back pennant-winning Royals teams (and another, Odorizzi, was used to acquire two other major contributors to those teams in Wade Davis and James Shields). Of course, two of those guys—Jeffress and, later, Cain—would come back and have good seasons in Milwaukee. I don’t think many fans begrudge the front office’s aggressive acquisition of Greinke, who at the time was one year removed from one of the best pitching seasons of the 21st century.

Finally, the 2022 trade of Josh Hader, who had over a year of team control remaining, was deeply unpopular; that team, who was three games ahead of the Cardinals in the division at the time, nose-dived afterward, and the trade is probably directly responsible for the end of David Stearns’ time as the Brewers’ general manager. But time and space put that trade in a different light: Robert Gasser looks like he can be a real contributor, and Esteury Ruiz was used to acquire William Contreras, as covered above.