PHOENIX — The World Series is right around the corner, with the Milwaukee Brewers and Tampa Bay Rays looking to win their first championship — while one former Arizona Diamondbacks pitcher is guaranteed to win his first no matter who comes out on top.
Aug 12, 2025; Arlington, Texas, USA; Arizona Diamondbacks starting pitcher Jake Woodford (41) comes on to pitch against the Texas Rangers during the fourth inning at Globe Life Field. Mandatory Credit: Andrew Dieb-Imagn Images
Former reliever Jake Woodford spent time with three teams during the 2026 season, starting with the Rays before landing with the Brewers. The Cubs then picked him up before he finished the season back with Tampa Bay.
Woodford pitched 23.1 innings for Milwaukee and 1.1 innings for Tampa Bay late in the year. Despite the short stints, the former D-Backs pitcher is in line to earn his first championship ring, whether the Brewers or Rays come out on top.
Jun 1, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Jake Woodford (41) and catcher William Contreras (24) celebrate a 16-2 win over the San Francisco Giants at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images
It’s not uncommon for players who have suited up for multiple teams to be guaranteed a ring when two of their former teams meet in the championship series. The last players guaranteed a ring were infielder Buddy Kennedy and pitcher José Ureña in the 2025 World Series, with both having played for the Los Angeles Dodgers and Toronto Blue Jays.
Woodford’s situation is particularly notable since he was just in the Valley a year ago. During his time with Arizona, he was part of a revolving-door bullpen, taking on different roles and situations throughout the season. He recorded a 6.44 ERA and three saves in a year the Snakes set an MLB record with 15 different relievers recording saves.
Feb 27, 2026; Port Charlotte, Florida, USA; Tampa Bay Rays pitcher Jake Woodford (41) throws a pitch during the third inning against the Toronto Blue Jays at Charlotte Sports Park. Mandatory Credit: Kim Klement Neitzel-Imagn Images
Woodford had a turbulent year in 2026, posting a 7.81 ERA to close out his season.
But the numbers don’t matter at this point — nor does which team lifts the Commissioner’s Trophy at the end of the series, with Woodford guaranteed to become a World Series champion.
Shoutout Jake Woodford – He’s guaranteed to become an MLB champion.
Played a game for the Rays.
Played 16 games for the Brewers. https://t.co/uxaaxlizJt— SleeperMLB (@SleeperMLB) October 20, 2026
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Wendy Lopez is a reporter for Burn City Sports. You can follow her on her X account, @wlopezde
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