Ryan Helsley Signs Two-Year Contract With Red Sox’s Division Rival

The Boston Red Sox and their fan base really shouldn’t sleep on the Baltimore Orioles heading into 2026, and another reason for that arrived on Saturday.

According to ESPN’s Jeff Passan, the Orioles and 2024 NL Reliever of the Year Ryan Helsley have agreed on a two-year contract. Helsley is expected to be Baltimore’s closer.

Shortly after Passan dropped the Helsley news, details arrived via other MLB insiders about the value of Helsley’s deal: $28 million over two years.

Despite a difficult 2025 stint with the New York Mets after getting traded from the St. Louis Cardinals, Helsley’s career has been defined by success. He burst onto the MLB scene as a hard-throwing right-hander, selected by St. Louis in the fifth round of the 2015 draft out of Northeastern State University. After honing his craft in the minors, he debuted in 2019, quickly evolving into a bullpen force with a fastball that routinely topped 100 mph and a wicked slider. By 2022, Helsley claimed the closer role, earning his first All-Star nod while posting a 1.25 ERA over 64.2 innings.

Helsley’s peak came in 2024, when he set a Cardinals franchise record with 49 saves (tops in the majors) alongside a stellar 2.04 ERA, 7-4 record, and 79 strikeouts in 65 appearances. That dominance earned him the National League Reliever of the Year award, cementing his status as one of baseball’s elite late-inning arms.

The 2025 season brought turbulence. Signed to an $8.2 million arbitration deal, Helsley started strong with St. Louis, securing 21 saves in 26 chances and a 3.00 ERA over 36 innings. But a toe injury and mechanical tweaks led to inconsistency. Then, on July 30, he was traded to Mets for three prospects: infielder Jesus Baez, pitcher Nate Dohm, and hurler Frank Elissalt. He stumbled in Queens, yielding a rough 7.20 ERA and 0-3 record across 20 innings in 22 games.