As the World Series approaches, one player, relief pitcher Jake Woodford, stands out for his unique journey this season. Despite the series not starting yet, Woodford finds himself linked to the success of both the Milwaukee Brewers and Tampa Bay Rays.
The 29-year-old Woodford began his unpredictable season when the Rays traded him to the Brewers in March. As a member of the Brewers’ bullpen, he appeared in 16 games, recording a 1-0 record, a 6.94 ERA, and one save over 23 1/3 innings.
On June 5, the Brewers designated Woodford for assignment, leading to his release. By July 4, he signed with the Chicago Cubs. However, his stint with the Cubs was brief, allowing three runs in two innings in his sole appearance by July 11. Following another release on July 16, the Cubs re-engaged him with a minor league contract on July 18. He returned to the major league roster on July 29, pitched a scoreless inning on August 3, but was designated for assignment again on August 4 and released on August 10.
On August 11, the Rays brought him back on a minor league contract. After over a month, they added him to their roster on September 24. Woodford faced the New York Yankees but allowed three earned runs in 1 1/3 innings. His release on September 29 closed his major league chapter for the season.
“Ring distribution is at the discretion of team ownership and management.”
Woodford’s journey took him through three teams during the 2026 season. Now, one of those teams will win the World Series. However, ring distribution decisions rest with team management, meaning Woodford may not receive a championship ring despite his contributions to both teams.
The World Series kicks off with the Brewers hosting the Rays, promising an exciting matchup. While Woodford’s presence on any team has come with no guarantees, his season highlighted the unpredictable and dynamic nature of professional baseball.

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