The narrative is that too many of Milwaukee’s favorite baseball players get away.
The most painful exodus was Paul Molitor signing with Toronto after the 1992 season. Greg Vaughn, Richie Sexson, Carlos Lee, Zack Greinke and Corbin Burnes all were traded before reaching free agency when it was clear the Brewers would eventually be outbid. Others who did get to free agency -- like CC Sabathia, Prince Fielder and Willy Adames -- all out-priced Milwaukee.
Not everybody left, however. Before losing Molitor to Toronto, the Brewers managed to keep him and Robin Yount together for 15 years, breaking the bank in the winter of 1989-90 for a three-year, $9.6 million pact to keep Yount from signing with the Angels. Ryan Braun stayed for his prime years. Ben Sheets and Yovani Gallardo stuck around, too.
In 2020, Christian Yelich did the same, prompting Milwaukee-raised Brewers manager Craig Counsell to push back against the narrative.
“We can go to every franchise and name players who have left,” Counsell said. “I think ownership here even before Mark [Attanasio, the Brewers’ principal owner] has really made that -- Mr. Selig kept two Hall of Famers in uniform here for a long time. Then I think Mark kept a really good player in Ryan Braun in uniform for a really long time. I don’t think you’re ever going to bat 1.000.”
Here’s a look at how the richest deals in Brewers history panned out:
1) Christian Yelich
Nine-year, $215 million contract
Signed: March 2020
Yelich was coming off two of the greatest individual seasons in franchise history when he committed to be a Brewer for life, adding seven years and $188.5 million to the two years he had remaining on his contract at the time. Because the extension required adding a no-trade clause to the final two guaranteed years on his former deal, and nixing a 2022 club option, it required a new nine-year contract.
He was also coming off a fractured kneecap, and about to head into an uncertain summer marked by the coronavirus pandemic and a shortened 60-game season. It’s impossible to measure the degree to which those factors, along with a balky back, influenced the years to come, but Yelich remained a mainstay for Milwaukee. He returned from back surgery to deliver one of his best years in 2025, hitting 29 homers with 103 RBIs to lead a Brewers club which paced MLB with 97 victories.
2) Ryan Braun
Five-year, $105 million extension
Signed: April 2011
Ken Rosenthal, who broke the news of Yelich’s extension, wrote a column for The Athletic in 2020 in which he referred to Braun’s extension as “a mistake.” Rosenthal cited Braun’s PED suspension in 2013, and some Brewers fans became frustrated when Braun missed time late in his career with minor injuries. But Braun should get credit for remaining productive deep into his 30s while some of the players from his stellar 2005 Draft class have either faded or fallen out of baseball entirely. He announced his retirement in 2021.
3) Jackson Chourio
Eight-year, $82 million contract
Signed: December 2023
Chourio was just 20 years old when he inked the deal at baseball’s Winter Meetings, setting an industry record for a player with zero Major League experience. The contract came with a place on the 40-man roster and a clear path to the Opening Day lineup at Citi Field, where Chourio became the youngest player to bat leadoff in his Major League debut on Opening Day since Hall of Famer Bobby Doerr in 1937. Chourio rose to the task, overcoming a slow start to his career to finish third in NL Rookie of the Year Award balloting that season.
4) Lorenzo Cain
Five-year, $80 million free-agent contract
Signed: January 2018
The Brewers agreed with Cain on the same day they traded for Yelich, marking the start of what became the longest stretch of sustained success in franchise history. Cain finished seventh in NL MVP Award balloting in 2018 and won a Rawlings Gold Glove Award in '19 before fading. He elected not to play the bulk of the shortened 2020 season, and he played in 121 more games in '21 and ’22 before the Brewers released him.
5) Matt Garza
Four-year, $50 million free-agent contract
Signed: January 2014
The Brewers made a public relations splash by announcing an agreement with Garza during their offseason fanfest in 2014, but it proved a bust. He had a 3.64 ERA in the first season but was limited to 163 1/3 innings. In the subsequent three seasons from 2015-17, Garza was 18-31 with a 5.10 ERA.
6) Braun
Eight-year, $45 million extension
Signed: May 2008
Braun traded future earnings potential for security when he signed a contract that set an MLB record for a player with less than one year of Major League service. He was the reigning National League Rookie of the Year at the time.
7) Jeff Suppan
Four-year, $42 million free-agent contract
Signed December 2006
One of the most polarizing contracts in franchise history was finalized on Christmas Eve. Suppan was 29-36 with a 5.08 ERA in a Brewers uniform, and while he did some of his best work down the stretch in 2008 when the team was chasing its first postseason appearance in 26 years, many fans are more likely to remember a disastrous start against the Phillies in Game 4 of the NL Division Series.
Tied for 8) Ben Sheets
Four-year, $38.5 million extension
Signed April 2005
Sheets showed up in shorts and a T-shirt for the press conference announcing what was at the time the richest contract in club history and a significant step for the Brewers under new owner Mark Attanasio. Injuries held Sheets back during the ensuing seasons, but when he was right, there was no one who was more fun to watch on the mound. Sheets was an All-Star in 2007 and ‘08 (he’s still the only Brewers pitcher to start an All-Star Game) and was having a fantastic season for the postseason-bound Brewers in ‘08 when he injured his elbow in September.
Tied for 8) Rickie Weeks
Four-year, $38.5 million extension
Signed: February 2011
The Brewers signed Weeks on the eve of an arbitration hearing, adding his name next to Braun, Yovani Gallardo and Corey Hart on a list of home-grown players signed to long-term contracts. Weeks was coming off his best season, a 29-homer, .830 OPS effort in 2010, when he led the Majors with 754 plate appearances. He was an All-Star in ‘11 but topped 500 at-bats in only one of the four seasons of the contract.
10) Aramis Ramirez
Three-year, $36 million free-agent contract
Signed: December 2011
The Brewers were facing Prince Fielder’s imminent departure in free agency and a potential suspension for Ryan Braun when they inked former Cubs third baseman Ramirez to a three-year guarantee that wound up being a $50 million deal when the sides each exercised a mutual option for a fourth season. Ramirez made good on the deal, posting an .815 OPS in a Brewers uniform, including a 5.4 fWAR season in 2012.
Other $30 million-plus deals
Rhys Hoskins
Two-year, $34 million free agent contract in January 2024
Kyle Lohse
Three-year, $33 million free-agent contract in March 2013
Yovani Gallardo
Five-year, $30.1 million extension in April 2010