Ranking the Brewers most impactful Trade Deadline deals in history

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.