5 Greatest Milwaukee Brewers Pitchers of All Time

It's not unreasonable to suggest Woodruff could one day take the No. 1 spot on this list, but for now, he slots in at No. 4. Woodruff was yet another diamond in the rough found by the Brewers as an 11th-round pick in the 2014 MLB draft after an inconsistent junior year at Mississippi State.

Ranked as the third-best prospect in the Brewers' system in 2018, Woodruff's best moment actually came in Game 1 of the NLCS against Clayton Kershaw and the Dodgers, and it wasn't even on the mound.

Woodruff, then a reliever, hit a game-tying home run off Kershaw in the third inning, his second career home run. While the Brewers would fall a game shy of their first NL pennant since 1982, they would win Game 1 owing much to the hitting heroics of Woodruff, who also got the win.

Despite his availability from 2023 to 2025 being hampered by shoulder and ankle injuries, Woodruff is the all-time Brewers' ERA leader and ranks No. 6 on the team's all-time strikeout total, and climbing.

MORE: Ranking the 5 Greatest Brewers Hitters Ever

3. Ben Sheets (2001-2008)

Sheets is one of the best homegrown stories in Brewers' franchise history, putting together a special eight-year tenure that included four All-Star nods.

His peak for the team came in 2004 -- also his best season, with a 2.70 ERA and 162 ERA+ (62% better than league average) -- where he set a single-game franchise record with 18 strikeouts against the Braves on May 14, 2004.

To top it off, Sheets struck out five straight batters to finish the game, putting the icing on the cake of a truly dominant outing.

Fans most fondly remember Sheets for being an integral part of the 2008 Brewers team that broke the 26-year postseason drought -- Sheets even started the 2008 All-Star Game for the National League in a squad that included Tim Lincecum and Kerry Wood.

2. Teddy Higuera (1985-1994)

Higuera has a legitimate case to be the best pitcher in Brewers history, as he nearly won NL Rookie of the Year as a pitcher in 1985, going 15-8 with a 3.90 ERA and finishing as the runner-up to the White Sox' Ozzie Guillen (the Brewers used to be in the AL, remember?)

The four-year span Higuera would rattle off following his rookie year are as good as anyone's in franchise history, putting together a league-leading 9.4 wins above replacement in 1986, posting a 2.79 ERA, and winning 20 games, finishing as the Cy Young runner-up to Boston's Roger Clemens.

His 240 strikeouts in 1987, then a franchise record, and throwing 33 consecutive innings similarly added him to the record books. All of Higuera's greatness, too, was defined in the context of his Mexican heritage.

1. RP Rollie Fingers (1981-1985)

OK, Rollie Fingers is (mostly) a reliever. OK, he only played four years in Milwaukee at the tail end of his career. And yes, he never eclipsed 80 innings in a season during his time in Wisconsin.

I'm looking past all of that when I argue for "Mr. Mustache" to be considered the best pitcher in Brewers history.

Fingers' 1981 season was arguably the best season by a pitcher in Brewers history, where he took home not only the Cy Young award but the AL MVP award as a pitcher in a league that included 56-stolen-base Rickey Henderson, who many say should have won the award.

Fingers' 1981 season, albeit shortened by a work stoppage, redefined the value placed on a reliever. It also validated the value of having a player with a 1.08 ERA and 28 saves at the back end of the bullpen, a presence that helped the Brewers make it to the playoffs for the first time in their history.

Fingers was similarly dominant in 1982, though his season was cut short by a torn forearm muscle in September. It's worth asking whether the Brewers would have won the World Series in 1982 had Fingers been available out of the bullpen. In 1985, Fingers set what was then the American League record for career saves with 232.

While his tenure in Milwaukee was brief relative to those on his list, it's hard to argue that Fingers wasn't deeply impactful to the franchise and sport during his time in Cream City.