Oct 23, 2026 12:00 AM

Spanning a chaotic season of trades and releases, journeyman Jake Woodford secured a World Series ring by pitching for both the Tampa Bay Rays and Milwaukee Brewers.

As the only player to appear for both the Tampa Bay Rays and Milwaukee Brewers in 2026, Jake Woodford will become a World Series champion regardless of which team wins the Fall Classic.

Woodford’s time with Brewers, Cubs and Rays

Woodford began the season in Spring Training with Tampa Bay before the Rays traded him to Milwaukee on Mar. 24.

The veteran right-hander appeared in 16 games for the Brewers, going 1-0 with a 6.94 ERA and 1.76 WHIP in 23.1 innings. He recorded 20 strikeouts and one save during his time with Milwaukee.

The Brewers eventually designated Woodford for assignment and outrighted him to Triple-A. They later released him on July 4, opening the door for a brief opportunity with the Chicago Cubs.

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Woodford made two appearances for Chicago before being released again. He allowed three runs on six hits (one home run) with three strikeouts in three innings during those outings.

Tampa Bay then brought Woodford back but gave him only one MLB opportunity after his return.

Woodford pitched against the New York Yankees on Sept. 24. He allowed three runs on three hits (one home run) with two strikeouts and one walk in 1.1 innings during Tampa Bay’s 6-4 road loss.

Woodford did not perform at a high level for either World Series participant, and his contributions may appear limited.

However, his unusual season provides a reminder of the numerous, often forgotten players who help teams navigate the long path toward the Fall Classic.

Reaching the World Series requires far more than the 26 players who leave Spring Training on the active roster. Injuries, fatigue, ineffective performances and schedule demands force every organization to rely on depth throughout the season.

Woodford’s mindset

Even respected pitching organizations such as Tampa Bay and Milwaukee need pitchers capable of accepting temporary assignments. Those appearances can protect other arms, cover unexpected innings and help a team survive difficult portions of the schedule.

Woodford’s season required persistence. He was traded before Opening Day, designated for assignment, sent outright to Triple-A and released twice.

Each move created uncertainty, yet he continued accepting opportunities whenever another organization called.

That willingness to remain prepared matters for pitchers who move between MLB and the minor leagues. They rarely receive the comfort of an established role or a predictable schedule.

Woodford needed to adjust to different coaches, catchers, teammates and organizational expectations throughout the year.

His results did not secure a permanent position, but his availability allowed three teams to use him when they required another arm.

Tampa Bay and Milwaukee reached the World Series because their entire organizations absorbed the demands of the season, not merely because their most prominent players performed.

While there are full circle stories like the ones from Jake Bauers and Freddy Peralta, Woodford represents that overlooked layer of roster construction.

His connection may be unusual, but it also reflects the instability endured by depth players. He will receive a World Series ring because he contributed to both teams that survived longer than everyone else.

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