Relief pitcher Jake Woodford has secured a World Series championship for the 2026 season before the final series begins, a result guaranteed by his roster movements between the Milwaukee Brewers and Tampa Bay Rays. The 29-year-old right-hander pitched for both teams during the regular season, ensuring he will be part of the winning organization when the postseason concludes.
Woodford began the year in the Brewers' bullpen after Tampa Bay traded him to Milwaukee in March. He appeared in 16 games for the Brewers, finishing with a 1-0 record, a 6.94 earned run average, and one save in 23 1/3 innings. The Brewers designated him for assignment on June 5 and released him shortly thereafter.
His path through the league then shifted to the Chicago Cubs, who signed him on July 4. Woodford made one appearance for Chicago, allowing three runs in two innings. The Cubs designated him for assignment on July 11 and released him on July 16, only to sign him to a minor league deal two days later. They selected his contract back to the major league roster on July 29. After pitching one scoreless inning on August 3, Woodford was designated for assignment again on August 4 and released on August 10.
Tampa Bay re-signed Woodford to a minor league contract on August 11. He spent more than a month in the minors before the Rays selected his contract and added him to their major league roster on September 24. In his return to the majors with Tampa Bay, Woodford faced the New York Yankees, giving up three earned runs in 1 1/3 innings. The Rays designated him for assignment on September 25 and released him on September 29.
Despite this series of transactions spanning three organizations, Woodford's status as a champion remains certain because one of those teams will win the series. The World Series opens Friday at 8 p.m. ET with the Brewers hosting the Rays. However, possession of a physical championship ring is not assured for Woodford. League rules do not mandate that teams distribute rings to every player who appears in the season; distribution is left to the discretion of team ownership and management.