Former Chicago Cubs reliever and WS Champion Ryan Pressly retires
After 13 seasons in Major League Baseball, two-time All-Star and 2022 World Series Champion with the Houston Astros, reliever Ryan Pressly announced his retirement from the game, according to The Athletic’s Ken Rosenthal.
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In his retirement announcement, the 37-year-old thanked all three major league teams he played for in his career: the Minnesota Twins (six years), the Astros (seven years), and the Chicago Cubs for the final season of his career in 2025. Pressly, who joined the Cubs after his former teammate Kyle Tucker got traded over, said of his time with the team, that he was thankful for “the Cubs for giving me a chance to pitch for such an iconic franchise. Wrigley Field, those North Side fans, unforgettable. Thank you.”
Ryan Pressly announces his retirement pic.twitter.com/RtpjWe1uIn
— Ken Rosenthal (@Ken_Rosenthal) January 17, 2026
Despite not pitching well for the Chicago Cubs, Ryan Pressly had a great career

Drafted in the 11th round of the 2007 MLB Draft by the Boston Red Sox, Pressly would make his debut on April 4, 2013, with the Twins after they drafted him in the 2012 Rule 5 Draft. One of the better closers in the game, Pressly, finished with a career record of 37-39 with a 3.33 ERA and saved 117 games in 691.1 innings (667 games).
Pressly has also shown to be one of the best postseason pitchers of all time, ranking fifth for saves (14). Pressly’s impressive resume made him a trade target of the Cubs, who needed an experienced closer with postseason experience to help them engage in their playoff push in 2025.
Sadly for both Pressly and the Cubs, things never panned out. In 44 games with the Cubs, Pressly had a 2-3 record with a 4.35 ERA and saved only five games in 41.1 innings. Pressly’s struggles and inability to refine what made him so dominant led to his release on Aug. 1.

The post Former Chicago Cubs reliever and WS Champion Ryan Pressly retires appeared first on ChiCitySports.
Source: https://www.chicitysports.com/former-chicago-cub-ryan-pressly-retires
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