Jake Woodford will receive a World Series ring—without ever pitching in it. Despite recording a 7.81 ERA and 25 strikeouts in 19 outings, Woodford is the luckiest player in MLB this season. Regardless of whether the Milwaukee Brewers or the Tampa Bay Rays lift the trophy, the 29-year-old reliever will be a champion either way. How? Check it out below.
“Being the only player to appear for both teams in 2026, Woodford will go down as a World Series champion no matter who wins!” noted the official MLB handle on X.
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The Brewers and the Rays are both chasing their first World Series title this season. But Jake Woodford has found himself in an unusual but fortunate situation, having pitched for the competing teams during the regular season. His 2026 journey has put the reliever in an enviable position at baseball’s biggest stage: he can’t lose regardless of the team that wins the Fall Classic.
2026 started with Woodford arriving at the Rays’ Spring Training camp. The franchise had signed the reliever on a minor league contract in November last year. However, Woodford did not advance to the big leagues with the Rays, as the team traded him to the Milwaukee Brewers on March 24.
The RHP saw the most action in the Brewers bullpen, mostly pitching mop-up. In 16 outings, Woodford recorded a 6.94 ERA in 23.1 innings.
Woodford’s struggles on the mound culminated in a DFA on June 5.
He cleared the waivers and subsequently became a free agent. Woodford began another brief stint when the Chicago Cubs signed him on July 4.
After just one game in which he allowed three runs in two innings, the Cubs designated Woodford for assignment and released him after a few days.
His roller-coaster of a journey continued when the Cubs signed him to a minor league contract. He returned to the Major League roster for one game only to be DFA’d again in August.
Following the DFA, Woodford returned to the Tampa Bay Rays.
His second spell with the Rays brought him back to the major leagues in September. However, he made just one appearance, pitching 1⅓ innings against the New York Yankees on September 24, allowing three earned runs. The Rays designated him for assignment shortly afterward, and he elected free agency at the end of September.
Despite the difficult season, Woodford’s time with both World Series participants has given him the opportunity to have a World Series ring under his name.
Notably, Woodford is not the first one to have such an opportunity in MLB history. Last season, infielder Buddy Kennedy and RHP José Ureña played for the Toronto Blue Jays and the Los Angeles Dodgers, guaranteeing them a World Series ring no matter the outcome.
Woodford logged 23⅓ innings for Milwaukee before moving on and later made a brief return to the Rays. Neither stint made him a likely candidate to appear in the World Series, but his regular-season involvement with both teams has made him a candidate for the championship ring.
In MLB, it is standard practice for a franchise to award World Series rings to any player who appeared in a game or was part of the organization during the season, even if they are no longer on the active roster or postseason roster. The decision to award rings is not governed by the league and is left entirely up to the team’s discretion. Woodford perfectly fits the case.
While Woodford is sure to keep track of the World Series, let’s have a look at his professional journey so far.
Jake Woodford— a journeyman pitcher
Jake Woodford’s journey in professional baseball has been marked by early promise, inconsistent performances, and several changes of scenery so far.
The right-hander’s pro career began more than a decade ago when the St. Louis Cardinals selected him as the 39th overall pick in the 2015 MLB Draft. After spending several seasons developing in the minor leagues, the right-handed pitcher made his major-league debut on August 15, 2020, against the Chicago White Sox.
Woodford showed promise as he established himself within the Cardinals organization in a versatile role: as a starter and reliever. He enjoyed encouraging campaigns in 2021 and 2022, with a combined 3.26 ERA across 116 innings during those two seasons. In 2022, he recorded a 2.23 ERA in 27 appearances, strengthening his position among the Cardinals’ pitching staff.
However, Woodford struggled to maintain that momentum in 2023. Shoulder inflammation limited his opportunities, and he finished the season with a 6.23 ERA in 15 appearances. St. Louis subsequently non-tendered him, making him a free agent and bringing his first major-league stint to an end.
Woodford began the 2024 season with the Chicago White Sox on a minor-league contract. He recorded only 2 big-league starts, allowing 10 earned runs, and was designated for assignment. Woodford then joined the Pittsburgh Pirates. Despite getting another opportunity to become a part of the MLB fixture, Woodford was unable to secure a permanent role.
The right-hander’s search for stability continued in 2025. He signed minor-league deals with several organizations, including the Colorado Rockies, New York Yankees and Chicago Cubs, before joining the Arizona Diamondbacks in July. Woodford appeared in 22 games for Arizona, recording a 6.44 ERA across 36⅓ innings.
The Diamondbacks designated him for assignment in September, and he elected free agency on October 1, leaving him in another uncertain situation until November.
In November 2025, the Tampa Bay Rays signed Woodford to a minor-league contract. The agreement included an invitation to spring training, giving the Florida native a chance to compete for a spot in MLB anew.