Jake Woodford’s Eventful Baseball Season Ahead of World Series

As the World Series approaches, player Jake Woodford finds himself in a unique position having played for both the Milwaukee Brewers and the Tampa Bay Rays this season. This ensures his affiliation with the championship-winning team regardless of the outcome. During the season, Woodford’s journey took him through several roster changes across multiple teams.

Before the season began in March, the 29-year-old was traded to Milwaukee from Tampa Bay. Initially part of the Brewers’ bullpen, Woodford participated in 16 games and secured a 1-0 record, a 6.94 ERA, and one save over 23 1/3 innings pitched. However, on June 5, he was designated for assignment by the Brewers and released shortly thereafter.

Jake Woodford faced the Detroit Tigers during a game on April 21, 2026, at Comerica Park in Detroit, Michigan.

Woodford signed a contract with the Chicago Cubs on July 4, appearing in only one game where he allowed three runs in two innings. The Cubs designated him for assignment by July 11, releasing him five days later. Nevertheless, Woodford rejoined the Cubs on a minor league deal on July 18; his major league contract was selected on July 29.

On August 3, he pitched a scoreless inning but was subsequently designated for assignment again on August 4 and released on August 10.

Jake Woodford wore Tampa Bay Rays colors for a photo at Charlotte Sports Park on February 19, 2026.

Returning to Tampa Bay in August, Woodford signed another minor league agreement with the Rays on August 11. After a month spent in the minor league, his contract was selected, and he joined the major league roster on September 24. On September 25, he was designated for assignment and released on September 29 after pitching against the New York Yankees.

Despite the tumultuous season across three different teams, one of them will emerge victorious in the World Series, theoretically making Woodford a championship player. However, receiving a championship ring isn’t guaranteed, as it’s at the team’s discretion. The World Series kicks off Friday evening at 8 p.m. Eastern Time, with the Brewers facing the Rays.