27. Rollie Fingers

Rollie Fingers arrived in Milwaukee in December 1980 through a major trade. His journey was quick; he had been with the St. Louis Cardinals for only four days. After acquiring Fingers from San Diego in an 11-player swap on December 8th, Cardinals GM Whitey Herzog, having also acquired Hall of Famer Bruce Sutter, decided to trade Fingers to Milwaukee on December 12th.

Fingers was sent to the Brewers alongside catcher Ted Simmons and starter Pete Vuckovich in exchange for a package that included Sixto Lezcano, Lary Sorensen, and prospects David Green and Dave LaPoint. While the Cardinals eventually won the 1982 World Series against Milwaukee, the Brewers essentially "won" the trade in the short term, as they netted the next two AL Cy Young winners in Fingers (1981) and Vuckovich (1982).

During the strike-shortened 1981 season, Fingers reached an absolute summit of performance that remains the gold standard for relief pitching. He authored a minuscule 1.04 ERA and led the league with 28 saves, allowing just nine earned runs over 78 innings of work. He showcased a total command of the American League, finishing the year with a 0.872 WHIP and proving to be the foundational spark that led the Brewers to their first-ever postseason berth. This masterpiece of a campaign made history; he became the first reliever to ever win the Cy Young Award and the MVP in the same season, a dual-honor plateau that remains one of the rarest feats in the game.

Fingers reached new postseason legend during the 1982 "Harvey's Wallbangers" run. Although he missed the World Series due to a torn forearm muscle, his regular-season contributions were vital to the team’s success. He recorded 29 saves with a 2.62 ERA, anchoring a bullpen that supported the team's potent offense. After a disabled list stint that caused him to miss the entire 1983 season, he returned with resilience, recording 23 saves in 1984, showing his veteran poise remained a key asset.

As his 17-year career's high-velocity innings took their toll, he finished his playing residency where it all started—in Milwaukee's Cactus League. He left with 97 saves and a 2.54 ERA, marking the final chapter of a Hall of Fame career. In 1992, the organization retired his number 34, symbolically honoring him.