The Orioles have signed right-hander Ryan Helsley to a two-year contract, ESPN’s Jeff Passan reports. The deal will pay Helsley $28MM in total, as per The Athletic’s Katie Woo. Helsley can opt out of the contract following the 2026 season, and the deal will be finalized once he passes a physical. The 31-year-old Helsley is represented by Wasserman.
Felix Bautista underwent shoulder surgery last August that will keep the closer on the injured list until at least August 2026, and that timeline means one setback could sideline Bautista for the entirety of the 2026 campaign. As a result, the Orioles headed into the offseason looking for multiple bullpen additions, including a pitcher with past experience as a closer.
Helsley fits that description, as he racked up 105 saves as the Cardinals’ primary ninth-inning choice from 2022-25. This stretch saw Helsley named to two NL All-Star teams, he was the NL’s Reliever Of The Year in 2024, and he even received some down-ballot Cy Young Award consideration in both 2022 and 2024. Overall, Helsley posted a 2.67 ERA, 29.12% strikeout rate, and 9.93% walk rate over 299 2/3 innings in a St. Louis uniform, from his debut with the team in 2019 until he was traded to the Mets at last July’s trade deadline.
Given the Cardinals’ struggles over the last few seasons and Helsley’s looming free agency, it was seen as a surprise that it took so long for the reliever to be traded. (In fact, the Orioles were first rumored to be interested in Helsley back in May 2024.) Even trading Helsley last winter in the wake of his excellent 2024 would’ve brought a greater return back to the Cardinals, though they still landed three prospects in the midseason deal with New York. And, considering how things went south for Helsley with the Mets, it’s hard to say the Cards didn’t come out on top in the deal.
Over 20 innings and 22 appearances with the Mets, Helsley was torched for a 7.20 ERA, with his home rate, strikeout rate, and walk rate all going in the wrong direction. Helsley felt he was tipping his pitches during his time in New York, but whatever the cause, the move back into a setup role behind Edwin Diaz ended up as a wash. Helsley’s struggles were one of the many reasons behind a disastrous second half for the Mets that saw the team slowly fade out of the playoff race and ultimately fall short of the postseason.
Despite this rough stretch, close to half the league reportedly had interest in Helsley on the open market. The Blue Jays, Cubs, and Tigers were among the many teams who saw Helsley as a bounce-back candidate and, intriguingly, Detroit and some other clubs viewed Helsley as a potential starting pitcher. Given how Helsley has never started a game at the MLB level, it would’ve been a surprising development to see him land somewhere as a rotation candidate, but he’ll now settle into his familiar closing role in Baltimore.
MLB Trade Rumors still ranked Helsley 36th on our list of the winter’s top 50 free agents. He topped our projection of a two-year, $24MM deal, and he might end up handily topping $24MM over a two-year timeframe depending on what happens with his opt-out clause. If he rediscovers his 2024 form, Helsley will surely chose to re-enter free agency in search of a more lucrative longer-term contract. The Orioles might not mind that scenario if Bautista is back healthy by that point, and Helsley could then be tagged with a qualifying offer heading into free agency next winter.
Helsley brings elite velocity and spin with his 99.3mph fastball, though batters teed off on Helsley’s fastball in 2025, and his slider has been the more effective of his pitches over the last few years. The righty has long struggled to avoid walks or hard contact, though the home run ball was never a huge issue until his brief stint with the Mets. It obviously wasn’t the ideal platform for Helsley as he entered free agency, yet it is understandable why the Orioles still felt comfortable in making a two-year investment in his services.
Even a two-year pact counts as a big step for an O’s front office that has been pretty conservative about investing heavily in free agents. Much of Mike Elias’ seven-year stint in charge of the baseball operations department was spent rebuilding, of course, but Tyler O’Neill’s three-year, $49.5MM deal from last winter is the only other multi-year contract Elias has even given to a free agent. The Orioles’ disappointing 75-win performance in 2025 may have raised the urgency level, as Baltimore has been linked to a number of top-shelf names in this year’s free agent market.
Between signing Helsley and re-acquiring old friend Andrew Kittredge, the back end of the Orioles’ bullpen looks much sturdier than it did at season’s end. More relievers could still be on the way, but Baltimore’s primary pitching need is now rotation help.
Inset photo courtesy of Brad Penner — Imagn Images
