As the MLB Winter Meetings came to a close on Thursday, three Philadelphia Phillies pitchers finalized new deals. Right-hander Mark Leiter Jr. and left-handers Hoby Milner and Michael Plassmeyer each found new destinations, with Leiter and Milner agreeing to one-year contracts and Plassmeyer settling for a minor league opportunity. Leiter signed with the Athletics, Milner joined the Chicago Cubs, and Plassmeyer landed with the Toronto Blue Jays.
Leiter, the son of former Phillies pitcher Mark Leiter, first reached the majors with Philadelphia in 2017. Over parts of two seasons in red pinstripes, he logged a 5.03 ERA across 39 appearances. He was claimed off waivers by Toronto late in 2018 but struggled there and did not return to the big leagues until resurfacing with the Cubs in 2022.
It was in Chicago where Leiter carved out a reliable role, posting a solid 3.85 ERA over three seasons. That performance earned him a midseason trade to the New York Yankees at the 2024 deadline. His stint in the Bronx was less successful, as his ERA crept to just under 5.00, leading the Yankees to non-tender him this offseason. Still, the 34-year-old quickly rebounded on the open market, securing a one-year, $2.85 million deal with the Athletics.
Milner, another second-generation major leaguer, also debuted with the Phillies in 2017. He impressed during his rookie campaign with a stellar 2.01 ERA, but his follow-up season unraveled. In 10 appearances, the sidearm lefty allowed nine baserunners while recording only 14 outs, a stretch often remembered for the Phillies’ questionable bullpen management at the time.
Philadelphia dealt Milner to the Tampa Bay Rays for cash in July 2018, though his results there were similarly underwhelming. Since then, he has bounced between the Angels, Brewers, and most recently the Rangers. Over the course of his career, the 34-year-old has accumulated 341 1/3 innings with a 3.82 ERA and has earned just over $6 million. This winter, he landed a one-year, $3.75 million contract with the Cubs, adding experience to a bullpen that struggled badly in 2025.
Plassmeyer is the least known of the three. The Missouri native has appeared in just three major league games. He delivered 7 1/3 innings of three-run baseball across two outings for the pennant-winning Phillies in 2022, but his lone appearance in 2023 went poorly, as he was tagged for nine earned runs in 3 2/3 innings.
Released in June of that season, Plassmeyer later spent time in the Pirates’ and Rangers’ organizations without returning to the majors. Now 29, he owns a 4.24 career ERA in the minors and has experience working both as a starter and out of the bullpen.
With his minor league deal in Toronto, Plassmeyer is expected to provide Triple-A depth for a Blue Jays club that has aggressively upgraded its rotation this winter, highlighted by the massive $210 million signing of strikeout ace Dylan Cease and the addition of Cody Ponce following his resurgence overseas.
