Ranking the Brewers most impactful Trade Deadline deals in history

The Major League trade deadline represents a contending team’s final opportunity to infuse proven talent into its roster. With the Milwaukee Brewers in postseason contention, this season’s deadline – 6 p.m. Eastern time Tuesday, becomes especially vital.

It also represents a chance for Senior Vice President and General Manager Matt Arnold to test himself against his peers acting against the least forgiving crucible of all – the clock.

In their more than half century history, the Brewers have been both buyers and sellers – probably more frequently the latter – at the trade deadline. A lot has already been written and more will be written about the 2024 team’s deadline needs.

But this is also a good time to look back on the Brewers’ deadline history, and especially at the last-minute deals they swung that infused real talent into the big league roster.

The deadline for non-waiver deals has been July 31 for as long as many fans can remember. But it was not always thus; prior to 1986, the trade deadline was June 15. With that in mind, here’s a chronological look at the most significant deadline trades made by the Brewers since their establishment in 1969.

June 15, 1970. The Brewers had barely settled into their relocation from a first season in Seattle when GM Marvin Milkes landed possibly the team’s first signature player.

At the deadline, Milkes sent pitching prospects Dick Baney and Buzz Stephen to Baltimore for Dave May, an outfielder frustrated in his attempts to break in to the Orioles’ championship lineup.

Neither Baney nor Stephen ever made much of a mark but May found a home in Milwaukee. A regular through 1974, he hit .303 with 25 home runs and 93 RBIs in 1973, when he represented the Brewers at the All Star Game.

May’s tenure with the Brewers ended in November of 1974 when he became the trade bait in the deal that returned all-time home run champion Henry Aaron to Milwaukee for a valedictory season. He returned briefly to the Brewers in 1978, his final season.

He was inducted onto the team’s Wall of honor in 2014.

June 15, 1977. The Brewers were foundering toward the bottom of the AL East early in the 1977 season, and GM Jim Baumer took the opportunity to look for pitching prospects.

The deadline trade he swung with Cincinnati found just such a prospect. At the cost of career minor leaguers Rick O’Keeffe and Garry Pyka, Baumer brought left-hander Mike Caldwell to the Brewers.

Caldwell was an interesting but often also a frustrating arm in 1977. Coming up with the padres in 1971, he had put together a 35-50 record as a combo starter-reliever. Already traded twice in the previous six months, he made 14 appearances with the Reds, all of them in relief.

Manager Alex Grammas made Caldwell a starter, giving him a dozen starting opportunities. But in 1978 Caldwell exploded to front of the rotation stardom, going 22-9 with a 2.36 ERA in 34 starts, 23 of them complete games. He finished second to Ron Guidry in that season’s Cy Young voting.

Caldwell won 16 games in 1979, and 17 in 1982, when he was a fixture in the rotation that outlasted Baltimore for the AL East title.

The Brewers lost the 1982 World Series to the St. Louis Cardinals, but Caldwell was the winner in Games 1 – a 10-0 shutout – and 5.

He retired following the 1984 season, with a 102-80 record for the Brewers, and joined May as a 2014 inductee onto the team’s Wall of Honor.

July 7, 2008. Ask Brewers fans to point to the biggest trade deadline deal in franchise history and they’re likely to agree on the trade pulled off by Doug Melvin that brought C.C. Sabathia to Milwaukee.

Sabathia was a free agent to be and thus a rental. But the Brewers were in no position to be picky; absent a playoff berth since 1982, they were breathing down the figurative necks of the division-leading Chicago Cubs as the deadline approached.

The Brewers sent four prospects to Cleveland as the price for Sabathia, the best of whom turned out to be Michael Brantley. But Sabathia’s half season was worth the expense.

He made a workmanlike 17 starts down the stretch, winning 11 of them against just two defeats. The Brewers still finished seven and a half games behind the Cubs, but they outlasted the Mets by one game to win the wild card. Sabathia’s final win, on the season’s concluding Sunday, was the post-season clincher.

July 12, 2011. The Brewers spent all of 2011 in an extended back-and-forth with the division rival St . Louis Cardinals. The difference that brought Milwaukee the regular season title may have been GM Doug Melvin’s deadline acquisition of closer Francisco Rodriguez from the Mets.

Rodriguez was already an established star, having helped the Anaheim Angels to the 2002 World Series win as a rookie.  He had 208 saves with the Angels and 95 more with the Mets before being acquired by Milwaukee for Danny Herrera and a minor leaguer.

Rodriguez pitched in 31 games with the Brewers in 2011, compiling a 4-0 record and 1.86 ERA. In those days the crew had John Axford for the saves, so Rodriguez filled the setup man role. During Milwaukee’s 2011 post-season run, he pitched in two NLDS games versus Arizona and three more against St. Louis in the NLCS, allowing just one run in five innings.

Traded away in July of 2013, Rodriguez returned as a free agent in 2015, only to be traded away again at season’s end. But he made a big impression during his Milwaukee tenure, good enough to be installed on the team’s Wall of Fame in 2021.

July 30-31, 2015. One of Doug Melvin’s last acts as general manager before stepping aside in August was also one of his best. At the 2015 deadline he pulled off a pair of deadline trades that landed the Brewers five players of future significance.

On July 30, Melvin shipped Mike Fiers, Carlos Gomez, and cash to the contending Houston Astros in exchange for four prospects. The four were reliever Josh Hader, starting pitcher Adrian Houser, plus outfielders Brett Phillips and Domingo Santana.

One day later, Melvin sent outfielder Gerardo Parra to the Orioles for starter Zach Davies. The cores of those two trades would become fixtures in Milwaukee’s rise to a position of division primacy.

Hader is of course the best known. Arriving as a regular in 2018, he saved 12 games that season, 37 the next, and 13 in the shortened 2020 season. He saved 34 more in 2021 and had 29 when he was dealt to San Diego at the 2022 trade deadline.

Houser made 97 starts for the Brewers through 2023, going 10-6 with a 3.22 ERA in 2022, his best season.

Davies had winning records in 2016, 2017 and 2019, leading the league in starts (33) in 2017.

In four seasons with Milwaukee, Santana batted .266 with 52 home runs and 155 RBIs.