The Cleveland Guardians started reshaping their bullpen for 2027 on Friday. Eleven days after the season ended in Game 6 of the ALCS, the front office decided on contract options for two veteran right handers. Shawn Armstrong and Trevor Stephan will not return on their current deals. The same announcement also added an infielder, Milan Tolentino, to the 40-man roster.
Some moves today.#GuardsBall | @GuardsInsider pic.twitter.com/0TwdzrpL0m
— Cleveland Guardians (@CleGuardians) October 30, 2026
Cleveland declined its half of Shawn Armstrong’s 2027 mutual option, which sends the thirty-six-year-old to free agency. He came back to Cleveland last winter on a one-year, $5.5 million deal after a terrific 2025 in Texas, where he posted a 2.31 ERA over 71 appearances. The reunion never matched that level. Armstrong went 2-1 with a 4.58 ERA and a 1.358 WHIP in 41 games, with 34 strikeouts over 35 1/3 innings. Vogt still trusted him in big spots and had him open Game 6 of the ALCS against the Rays. Armstrong gave up a run in his lone inning that night and took the loss.
Stephan’s decision came as less of a surprise. The Guardians declined his 2027 club option, which ends the four-year, $10 million extension he signed in the spring of 2023. Cleveland took him from the Yankees in the Rule 5 draft before the 2021 season, and he quickly became one of the more exciting young arms in the bullpen. His 2022 season was outstanding: a 2.69 ERA across 66 games with 82 strikeouts in 63 2/3 innings.
Injuries took over from there. Stephan had Tommy John surgery after the 2023 season and has not pitched in the majors since. His velocity was down when he returned to the mound in the minors, and Cleveland eventually took him off the 40-man roster. He stayed in the organization through 2026 but never made it back to Progressive Field. He will turn thirty one next month and now hits the open market hoping someone gives him another chance.
The Guardians also selected the contract of Milan Tolentino from Triple-A Columbus. The 24-year-old was a fourth-round pick in 2020 and plays shortstop, second base and third base. In 2025, he became the first player in Clippers history to reach 20 home runs and 20 stolen bases in the same season. Adding him to the 40-man roster keeps a versatile infielder in the organization.
Together, these moves give Cleveland more payroll room and roster flexibility heading into a busy winter. Austin Hedges, Rhys Hoskins, Nathaniel Lowe and Foster Griffin are already free agents, and the front office still has to rebuild the depth around closer Cade Smith. Armstrong and Stephan will not be part of that, so expect the Guardians to look for new arms in the coming weeks.
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