Oct 22, 2026 4:43 PM
Reliever Jake Woodford secured a championship ring before the first pitch of the Fall Classic, thanks to a nomadic season spent with both World Series contenders.
The Chicago Cubs obviously fell short of winning a World Series this season.
The Cubs no doubt had World Series aspirations. They were extremely active at the trade deadline to upgrade their roster and went all in to try to return to the World Series. That led to the front office making some significant moves at the deadline.
The Cubs acquired Kevin Gausman, Clay Holmes, Tyrone Taylor, Braxton Garrett, and Ryan Zeferjahn at the trade deadline. They also acquired veteran David Peterson earlier in the season when injuries to their rotation began to surface.
However, those moves weren’t enough for the North Siders to make it back to the World Series. They were eventually swept in the National League Wild Card Round by the San Diego Padres, and the organization failed to make it to the National League Championship Series for the ninth straight year.
At the end of the day, this was a disappointing season. There was some hope building that this Cubs team could make a deep postseason run and get that World Series ring. Pete Crow-Armstrong had a career year, Alex Bregman was one of the best hitters in the sport in the second half, and Seiya Suzuki continued to hit the ball well at the top of the lineup.
While those players won’t be taking home a World Series ring this year, one former Cubs player from this season will. Reliever Jake Woodford will get a World Series ring no matter the result of the World Series matchup between the Milwaukee Brewers and Tampa Bay Rays.
Woodford began the season with the Brewers after the Rays traded him to Milwaukee on the eve of the regular season. The veteran right-hander then spent a little less than three months with the Brewers before being released by the organization on July 4.
The Cubs then signed Woodford to a Major League contract following his release. The 29-year-old pitched two games for the team on July 10 and August 3 and was eventually granted his release after being optioned to the Minors on August 7.
That’s when the Rays swooped in and signed him to a Minor League deal on August 11. Woodford spent the rest of the regular season in the Rays organization before electing free agency at the conclusion of the year.
Since Woodford pitched in at least one game for both the Brewers and Rays this season, he will receive a World Series ring no matter the outcome.
At least one Cubs player from this season will win a ring.
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