RESOLVING THE LEDGER
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SportsMoney Phillies Acquire Veteran AL Starter With Unique Agreement By Peter Chawaga ,
Forbes contributors publish independent expert analyses and insights. Peter Chawaga is a writer and editor covering Major League Baseball. Follow Author Aug 29, 2026, 06:30am EDT --:-- / --:-- This voice experience is generated by AI. Learn more . This voice experience is generated by AI. Learn more . Summary The Phillies are actively seeking pitching depth to bolster their playoff push and challenge the Braves, as their bullpen has shown inconsistency and key additions are sidelined. Manager Don Mattingly faces uncertainty in high-leverage situations. To address this, the team has signed former Minnesota Twins top prospect Josh Winder to a two-year minor-league contract. Winder, a 28-year-old right-hander, was once highly regarded but has seen his career impacted by injuries, including a recent Tommy John surgery diagnosis. This multi-year deal offers him a chance to rebuild within the Phillies system, potentially filling a middle relief role in the future.
The Phillies have spent much of the season searching for reliable pitching depth, and that need has become even more important as they try to secure a postseason spot and close the gap on the Atlanta Braves.
After numerous setbacks to the pitching staff, manager Don Mattingly doesn’t seem quite sure who he can turn to in high leverage spots, an issue that will only grow if the team makes a playoff run.
“The Phillies tweaked the bullpen in the offseason. But their most expensive addition, Brad Keller, had Tommy John elbow surgery last month,” The Philadelphia Inquirer’s Scott Lauber noted . “Jonathan Bowlan has outkicked expectations. But holdovers Kerkering and Alvarado have been inconsistent. So, as the Phillies attempt to cement a wild-card spot and close in on the division-leading Braves, the bullpen is coming into focus again, with relievers jockeying for position behind (Jhoan) Duran in Mattingly’s circle of trust.”
Now, the search for additional arms has led the Phillies to an unusual late-season agreement with a former American League starter and top pitching project.
On Thursday, news surfaced that the Phillies had signed right-hander Josh Winder to a two-year minor-league contract, according to multiple sources , giving the organization another potential depth option as the postseason approaches.
Winder, 28, was once viewed as one of the more intriguing young pitchers in the Minnesota Twins organization. Injuries, however, have significantly altered the trajectory of his career.
“Winder, 28, was a promising prospect not too long ago but injuries have derailed him in recent years,” Darragh McDonald noted for MLB Trade Rumors . “In 2021, he posted a 2.63 ERA across 14 minor league starts.”
Winder was originally selected by Minnesota in the seventh round of the 2018 MLB Draft. He steadily climbed the organization's system before reaching the majors. Baseball America ranked him as the No. 6 prospect in Minnesota's system entering the 2022 season. That season, he made 15 appearances, including 11 starts, and posted a 4.70 ERA with 47 strikeouts across 67 innings. He subsequently transitioned more heavily toward relief work before injuries again interrupted his progress.
Winder's career took another difficult turn after he signed with the Arizona Diamondbacks in January 2025. He was subsequently diagnosed with an elbow injury requiring Tommy John surgery and was released by Arizona shortly afterward.
That history makes his agreement with the Phillies notable.
Rather than simply serve as a short-term organizational addition, Winder now has multiple seasons attached to his deal to potentially rebuild his career within the Phillies system. And it seems possible he could enter the team’s circle of trust for a middle relief role sooner or later.
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