One of the busiest transaction seasons on the Major League Baseball calendar is, historically speaking, a relatively recent phenomenon.

From 1922 until 1985, the American and National Leagues—then operating as separate entities—banned trading after June 15 unless the players involved had cleared waivers. A few notable Brewers joined the team in mid-season trades under this model. Outfielder Dave May was the first among them, coming over from Baltimore in 1970, and the Crew acquired pitcher Mike Caldwell from the Reds in 1977. In 1986, the two leagues agreed to move the non-waiver trade deadline to the end of July, however, and the trade season as we know it was born.

The first decade under the new deadline was relatively quiet for the Brewers. They acquired 40-year-old, 21-year veteran pitcher Jerry Reuss from the White Sox in 1989 and sent scuffling outfielder Tom Brunansky to the Red Sox in 1994, but the trajectory of the franchise was hardly altered by either move.
As such, all of the most notable trade deadlines in franchise history have happened in the last 22 years. Here are the five busiest, best, and most productive trade deadlines in Milwaukee Brewers team history.

2008
The most storied in-season trade in Brewers franchise history, both in terms of historic significance and impact, has to be the 2008 deal that brought CC Sabathia from Cleveland to Milwaukee in a five-player swap. The Brewers were en route to their first postseason appearance in 26 years and got there largely on the back of their new ace, whose partial season in Milwaukee still stands as one of the greatest pitching performances in franchise history.

Meanwhile, the most impactful player dealt away in the transaction wasn’t even known at the time: Former first round pick Matt LaPorta had a forgettable MLB career, but outfielder Michael Brantley, the player to be named later in the trade, is still with Cleveland and will make his third All-Star appearance next week.
It’s worth mentioning that Sabathia wasn’t the Brewers’ only acquisition that trade season: they also acquired second baseman Ray Durham from the Giants. He replaced Rickie Weeks at second base down the stretch and batted .280 with a .369 on-base percentage and .477 slugging percentage in the final 41 games of his MLB career.

2015
A major trade deadline buy made it possible for the Brewers to win in 2008, but an epic fire sale in 2015 may have paved the way for the organization’s current success.

Over a span of eight days in 2015 Doug Melvin, in his final months as Brewers general manager, dealt third baseman Aramis Ramirez, outfielders Carlos Gomez and Gerardo Parra, and pitchers Mike Fiers and Jonathan Broxton. Combined, Milwaukee received seven players in return, including five that have played for the Brewers in 2018 and one (Josh Hader) that’s about to play in his first All-Star Game.

2012
Less than 24 months after acquiring Zack Greinke and making a clear statement that they were “going for it” in 2011, the Brewers were well out of contention in 2012. Thus, they took advantage of an opportunity to recoup some of their prospect expenses by dealing their new ace. They sent Greinke to the Angels for a three-player package that included infielder Jean Segura, who Baseball America had ranked as the No. 55 prospect in all of baseball before that season.

Segura paid near immediate dividends for the Brewers, shoring up a shortstop position that had been somewhat suspect in recent years and making the All-Star Game in his first full season in 2013. The deal did not work out as well for the Angels, who missed the postseason despite a solid finish from Greinke. That winter, they lost the star pitcher in free agency.

2000
A last-minute decision to sell caught some within the organization off guard in 2000, as the Brewers dealt closer Bob Wickman (along with pitchers Steve Woodard and Jason Bere) to Cleveland just one day before the team was scheduled to give away posters in honor of Wickman’s recent All-Star appearance. The promotion went on without him.

Promotional problems aside, the trade ended up working out well for Milwaukee, who acquired first baseman Richie Sexson as part of the return. Between 2001 and 2003 Sexson appeared in 477 of a possible 486 games for the Brewers, hitting 119 home runs and generally serving as a rare bright spot during a pretty bleak time in franchise history.

This deal also featured a less-heralded player that turned out to be significant: Infielder Marco Scutaro was the player to be named later in this trade. You might recognize him from another story.

2016
The Brewers continued the tear-down portion of their rebuild with one final purge during the 2016 season, dealing catcher Jonathan Lucroy, along with relievers Jeremy Jeffress and Will Smith on the same day in two separate transactions.

None of the five players who came back to the Brewers have made a major impact at the MLB level to date, but one (outfielder Lewis Brinson) was the centerpiece of the later trade bringing Christian Yelich to Milwaukee. Meanwhile, Jeffress has since returned to the Brewers organization for a third stint and has turned his career around.

Honorable mentions
It would feel incomplete to finish this list without mentioning Greg Vaughn, sent to the Padres in a five-player deal in 1996. Vaughn was a two-time All-Star who hit 169 home runs as a Brewer before going on to hit 95 in a two-year span with the Padres and Reds in 1998 and 1999.

The Brewers sold another slugger in 2006 (well, actually two), dealing Carlos Lee and a prospect by the name of Nelson Cruz to the Rangers in a six-player trade. The Brewers’ return in that transaction included a future All-Star closer (Francisco Cordero).

The 2011 Brewers made a series of small splashes leading up to the deadline, acquiring reliever Francisco Rodriguez, infielder Felipe Lopez, and the versatile Jerry Hairston Jr. in a series of transactions.

Conversely, the 2007 Brewers made some decisions that didn’t work out as well. They sent three pitching prospects to the Padres for reliever Scott Linebrink, who was inconsistent across 27 outings for Milwaukee, and dealt future All-Star closer Grant Balfour to the Rays for pitcher Seth McClung.

For over 10 years, Kyle Lobner has produced the Frosty Mug, a daily roundup of all things Brewers. Sign up to support Kyle’s work and receive the Mug in your inbox each weekday morning at Patreon.com/FrostyMug.

About The Author

Kyle Lobner

Kyle Lobner has remarkably poor hand/eye coordination and his batting stance looked like a much fatter Jeff Bagwell. Like most of the un-athletic people you know, he writes about baseball. He's done that at Brew Crew Ball, Milwaukee Magazine, Shepherd Express, and TimberRattlers.com.