As the MLB Winter Meetings wrapped up on Thursday, three former Philadelphia Phillies pitchers secured new contracts this week. Right-hander Mark Leiter Jr. and left-handers Hoby Milner and Michael Plassmeyer found new homes. Leiter and Milner landed one-year deals with the Athletics and Chicago Cubs, respectively, while Plassmeyer settled for a minor league pact with the Toronto Blue Jays.
Leiter, the son of former Phillies hurler Mark Leiter, made his big league debut in red pinstripes back in 2017, working to a 5.03 ERA across 39 appearances in two seasons for the club. The Blue Jays claimed him off waivers at the tail end of 2018, but he failed to impress and didn’t resurface in the big leagues until 2022 with the Cubs.
Leiter found his niche on the North Side, posting a rock-solid 3.85 ERA in three seasons before being dealt to the New York Yankees at the 2024 trade deadline. He took a step back in the Bronx, putting up an ERA just south of 5.00, and was non-tendered this winter. However, the 34-year-old has managed to land on his feet, securing a one-year, $2.85 million commitment from the nomadic Athletics.
In addition to Mark Leiter Jr. former Phillies Hoby Milner and Michael Plassmeyer landed with new clubs this week
Another second-generation big leaguer, Milner came up with the Phillies the same year as Leiter and provided an excellent 2.01 ERA in his rookie year. Unfortunately, the sidewinding lefty was strafed in his sophomore campaign, surrendering nine baserunners and recording only 14 outs in 10 appearances. Milner is perhaps best known as the victim of Gabe Kapler’s atrocious handling of the bullpen during his time as Phillies manager.
The Tampa Bay Rays acquired Milner for cash in July of 2018, but he didn’t fare much better there. He bounced from the Los Angeles Angels to the Milwaukee Brewers since then and spent this past season with the Texas Rangers.
Overall, the 34-year-old has provided 341 1/3 lifetime innings of 3.82 ERA work and has earned a bit over $6 million in his career. Milner earned himself a one-year, $3.75 million deal from the Cubs, bolstering a bullpen that struggled mightily in 2025.
Plassmeyer is the most obscure of the trio of former Phillies, as the southpaw has only appeared in three MLB games to date. The Missourian fired 7 1/3 innings of three-run ball in two games for the pennant-winning 2022 club, but was shelled in his sole 2023 game, yielding nine earned runs in 3 2/3 frames.
Plassmeyer was cut loose in June of that year and floated to the Pittsburgh Pirates and Texas Rangers organizations in ensuing seasons, failing to reach the majors at either stop. All told, the 29-year-old offers a decent 4.24 career minor league ERA and has plenty of experience as both a starter and relief pitcher.
Having signed a minor league deal with Toronto, Plassmeyer will likely serve as Triple-A depth for a Blue Jays team that has gone all in on starting pitching this winter, reeling in strikeout artist Dylan Cease for $210 million, as well as Cody Ponce who reinvented himself in Korea this past season.