Orioles Sign Ryan Helsley to Bold Two-Year Deal With a Twist

In a rare free-agent splash, the Orioles bolstered their bullpen by signing former All-Star closer Ryan Helsley to a multi-year deal amid uncertainty surrounding Felix Bautistas injury timeline.

The Orioles just made a significant move to reinforce the back end of their bullpen, officially signing right-hander Ryan Helsley to a two-year, $28 million deal. The contract includes an opt-out after the 2026 season and a $500,000 bonus if he’s traded. It’s a bold step for a front office that’s historically been cautious in free agency, and it signals Baltimore’s intent to bounce back after a disappointing 2025 campaign.

Let’s start with the context. The Orioles have a massive hole in the ninth inning with Félix Bautista sidelined until at least August 2026 following shoulder surgery.

And with the possibility of a setback pushing his return even further, the O’s needed someone who could handle high-leverage situations - and potentially take over as the closer. Helsley fits that mold perfectly.

From 2022 to 2025, Helsley was one of the most dominant late-inning arms in the National League. He notched 105 saves as the Cardinals’ go-to closer, earned two All-Star nods, took home NL Reliever of the Year honors in 2024, and even received Cy Young consideration in 2022 and 2024. That’s not just a strong résumé - that’s elite-level production over a sustained period.

Across his time in St. Louis, Helsley posted a 2.67 ERA over nearly 300 innings, striking out just under 30% of the batters he faced while keeping walks under 10%. He brought high-octane stuff and a fearless mentality to the mound - the kind of presence that can anchor a bullpen.

But then came the trade to the Mets at last year’s deadline, and things took a sharp turn. In 22 appearances for New York, Helsley struggled mightily, posting a 7.20 ERA.

His strikeout rate dropped, his walk rate climbed, and he gave up more home runs than usual. He later suggested he may have been tipping pitches, but regardless of the cause, his short stint in Queens didn’t go as planned.

Moved into a setup role behind Edwin Díaz, Helsley never found his footing, and his struggles mirrored the Mets’ second-half collapse.

Despite that rough patch, interest in Helsley remained strong once he hit the open market. Nearly half the league reportedly checked in, with teams like the Blue Jays, Cubs, and Tigers viewing him as a prime bounce-back candidate.

Some clubs even considered the possibility of stretching him out as a starter - a surprising thought, given he’s never started a game at the MLB level. But in the end, Helsley lands in a spot that plays to his strengths: closing games for a team with postseason aspirations.

This signing also reflects a shift in Baltimore’s approach. Under GM Mike Elias, the Orioles have been methodical with free agent spending, focusing primarily on internal development and short-term deals.

In fact, the only other multi-year free agent contract Elias has handed out was to Tyler O’Neill last winter. But after finishing 75-87 in 2025, the urgency has clearly ramped up.

Baltimore is being linked to several high-profile names this offseason, and the Helsley signing could be the first of several notable moves.

From a performance standpoint, Helsley still brings elite-level tools. His fastball averaged 99.3 mph last season, and he pairs it with a high-spin slider that’s been his most effective pitch in recent years.

That said, hitters were able to square up his fastball more often than usual in 2025, and his command has always been a bit of a wild card. Walks and hard contact have been part of his profile, but until his time with the Mets, the long ball hadn’t been a major issue.

The Orioles are betting that his New York stint was an outlier - and if he returns to form, this could be a steal. Should Helsley dominate in 2026, he’ll have the chance to opt out and test the market again, potentially landing a longer, more lucrative deal. And if Bautista is healthy by then, the O’s could let Helsley walk with a qualifying offer attached, giving them some flexibility.

In the meantime, Baltimore’s bullpen just got a serious upgrade. Pairing Helsley with recently re-acquired Andrew Kittredge gives manager Brandon Hyde two veteran arms capable of handling late-inning pressure. More reinforcements could still be on the way, but the bigger need now shifts to the rotation - an area the Orioles are expected to address as the offseason unfolds.

For a team trying to climb back into contention, this is the kind of move that makes a difference. Helsley has the track record, the stuff, and the mindset to lock down games. And if he pitches anything like he did in 2024, Camden Yards might be hearing a lot of “Helsley Time” in the ninth inning.