Prior to Wednesday night's title-clinching World Series Game 5 at Tropicana Field, Dustin May already knew what it's like to pop champagne after a championship-clinching victory. That experience set him apart from nearly all of his Brewers teammates.
The 2026 Brewers were the fourth World Series-winning team that May has been a part of in some form and the second for which he actually appeared in the Fall Classic, after his 2020 rookie season with the Dodgers. May was a bystander to Los Angeles' 2024 championship season, due to injury, and he also earned a ring as a member of the 2025 Dodgers, who traded him to the Red Sox at the Deadline.
For this exercise, winning the World Series is defined as playing at least one game in the series for the champions. By that metric, only May qualified as a champion before Wednesday night’s victory. World Series MVP William Contreras technically had a ring with the Braves in 2021, but he didn’t appear in the World Series despite holding a roster spot.
So let’s take a look at some of Milwaukee’s notable first-time champions who certainly waited their turn to reach baseball’s mountaintop.
Christian Yelich
34 years old, 14th MLB season
Milwaukee’s captain helped revive the franchise after a blockbuster trade in 2018 that included four prospects. He captured the 2018 National League MVP Award in his first year with the club, and now he has helped bring home their first title.
In the 2026 postseason, Yelich batted .268 with four stolen bases and six runs scored. He recorded two hits in the Brewers’ Game 3 rout of Tampa Bay and set the tone with his baserunning.
Brandon Woodruff
33 years old, 9th MLB season
Woodruff authored one of the feel-good stories of the World Series, coming out to close Game 3 in his first appearance since July. Selected in the 11th round of the 2014 Draft out of Mississippi State, he’s Milwaukee’s longest-tenured player.
Shoulder injuries over the last few seasons have derailed Woodruff's career and made him a question mark to even be included on the World Series roster. But he’s now a World Series champion for the team that drafted him.
Jake Bauers
31 years old, 7th MLB season
Bauers famously almost retired from baseball two years ago after a journeyman career across five different organizations. He stuck it out, and in his third year with Milwaukee, Bauers won NLCS MVP and delivered one of the biggest home runs in franchise history.
The left-handed slugger struggled in the World Series against his former team with just two hits in 21 at-bats. But after an .874 OPS on the year, he’ll be a highly coveted free agent on the market.
Trevor Megill
32 years old, 6th MLB season
Megill finished off Milwaukee’s first championship by pitching the last two innings of Game 5. It was a long time coming for Megill, who debuted at 27 years old in 2021 with the Cubs.
The closer is in his fourth organization after being taken in the Rule 5 Draft, being claimed off waivers twice and ultimately being traded from the Twins to the Brewers for Minor League reliever Taylor Floyd and cash. He finished the postseason with 11 strikeouts and two earned runs allowed in nine innings.
Gary Sánchez
33 years old, 12th MLB season
Once a top prospect in the Yankees farm system, Sánchez is now with his sixth organization, serving as the backup to Contreras, one of the game’s best catchers. Sánchez hammered 12 home runs in 2026, bringing his career total over 200.
Sánchez appeared twice in the World Series, recording a groundout as a pinch-hitter in Game 1 and catching the ninth inning of Game 3.
Antonio Senzatela
31 years old, 10th MLB season
Senzatela signed with the Rockies out of Venezuela in 2011, debuting in the Majors in 2017 before signing a five-year, $50.5 million extension. He was dealt to Milwaukee at this year's Trade Deadline and allowed no earned runs in 4 1/3 postseason innings.
Senzatela has a $14 million club option in 2027, then will become an unrestricted free agent for the first time.
JoJo Romero
30 years old, 7th MLB season
Romero is another bullpen piece Milwaukee added at the Trade Deadline, coming over from St. Louis with May. He allowed only one earned run in eight innings during the postseason, serving as a top left-handed option for manager Pat Murphy.
The southpaw was a fourth-round pick by the Phillies in 2016 out of Yavapai College in Arizona and was dealt to the Cardinals in 2022.