The 2026 Major League Baseball season came to an end on Wednesday night when the Milwaukee Brewers defeated the Tampa Bay Rays to win their first championship in franchise history. The Philadelphia Phillies may have bowed out of the postseason early on, but there were a handful of former Phillies who contributed to the Brewers’ historic season.
Brewers president of baseball operations Matt Arnold brought in Jojo Romero at the trade deadline to bolster the bullpen. The 30-year-old was a fourth-round draft pick by the Phillies back in 2016 and made his big league debut in red pinstripes in 2020. The Californian struggled in parts of three seasons in Philly, posting a 7.89 ERA over 25 outings before being flipped to the St. Louis Cardinals at the 2022 trade deadline.
The man coming back in exchange for Romero was Swiss Army knife Edmundo Sosa, who has become a fan favorite over the past half-decade. Sosa has posted a solid .746 OPS during his time with the Phillies, while Romero put up an excellent 3.07 ERA over five years in St. Louis; the trade was a win for both clubs. More importantly, Romero worked to a 3.38 mark down the stretch in Milwaukee and became one of manager Pat Murphy’s go-to options in the playoffs. Both Sosa and Romero are now free agents.
The other former Phillie to earn himself a ring this year as a player was swingman Bryse Wilson. The 28-year-old was brought in by the Phillies on a minor league deal last December and spent most of his time with the organization in Triple-A. He appeared in one game with the parent club on June 18th, tossing two scoreless innings in relief.
After that, the Chicago Cubs took a flier on Wilson, but they cut him loose once again just two weeks later. The Brewers picked him up in July, and he posted a 3.51 ERA across 13 outings. Wilson wasn’t on Milwaukee’s playoff roster, but he’ll still get a ring for his efforts.
Some former Phillies played a part in the Brewers championship both on and off the field
Aside from those two players, a handful of Brewers front-office personnel have ties to the Phillies. Area scout Pete Orr spent parts of three seasons in Philadelphia, posting a .599 OPS across 96 total games. Longtime Miami Marlins slugger Justin Bour was acquired in August of 2018 as a waiver trade and made his way into 29 games with the Phils, in which he hit just one homer. The 38-year-old now serves as a player development assistant with the Brewers.
Other former Phillies who are celebrating tonight:
— Phillies Tailgate (@PhilsTailgate) October 29, 2026
Matt Klentak- Executive Advisor to the GM
Pete Orr- Area Scout
Justin Bour- Player Development Assistant https://t.co/yIMYUjQdnN
Last is Matt Klentak. The former wunderkind was hired as the Phillies’ general manager in October of 2015, taking over for longtime punching bag Ruben Amaro Jr. Klentak oversaw some of the darkest years of the Phils’ decade-long rebuild, with his club posting an ugly 326-382 record over his five seasons at the helm, not once reaching the postseason.
Klentak did do some good during his time with the organization, reeling in superstars Bryce Harper and Zack Wheeler in free agency and negotiating a very team-friendly contract extension with ace Aaron Nola. Plus, he pulled off an all-time heist of a trade for catcher J.T. Realmuto. Despite those high points, Klentak was shown the door after the 2020 season and replaced with veteran executive Dave Dombrowski.
Klentak latched on with the Brewers in January of 2022 and now serves as an executive advisor to the general manager. It’ll be interesting to see if Klentak and the rest of the front office’s success this season launches him into a higher-profile role with another club this winter.
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