Baltimore Orioles Take a Smart Gamble, Sign Ryan Helsley to $28 Million Deal

The closer market is moving in free agency! First, Raisel Iglesias re-signed with the Atlanta Braves on a one-year deal, and now Ryan Helsley finds a new home in Baltimore.

According to ESPN’s Jeff Passan, the Orioles are signing Helsley to a two-year deal. Katie Woo of The Athletic was the first to report that the deal is worth $28 million. The contract includes an opt-out after the 2026 season.

There had been some reports that teams were considering converting Helsley to a starting pitcher, but Passan added in his report that Helsley is being signed to become the Orioles’ new closer.

Last year, the Orioles enjoyed the return of Felix Bautista pitching in the ninth inning, after the homegrown All-Star missed all of the 2024 season recovering from Tommy John surgery. Bautista made 35 appearances and saved 19 games, pitching to a 2.60 ERA in 2025.

Unfortunately, the healthy return would not last, as Bautista hit the IL with a shoulder injury, which eventually required surgery to repair a torn rotator cuff and a torn labrum. With the surgery taking place at the end of August, Bautista may miss all of the 2026 season.

Enter, Hells Bells.

Helsley has been one of the best closers in baseball over the past few years, but he is coming off an absolutely disastrous finish to his season after getting traded at the deadline to the New York Mets.

Whether it was the pressure of pitching in a big market for the first time in a pennant race or simply due to the reported issues of pitching tipping, Helsley endured the worst struggles of his career, which saw him pitch to a 7.20 ERA in 20 innings with the Mets.

We will see if Helsley can put the best behind him and get back to the guy on the back of the baseball card who has 105 career saves and has pitched to a career 2.96 ERA.

Is Helsley a Good Gamble for the Orioles?

The Baltimore Orioles were never going to play at the very top of the free agent market to land Edwin Diaz, but settling on Ryan Helsley is still a big-time move.

Behind Diaz, Robert Suarez, and Devin Williams are likely the two most highly sought-after closers on the market, with Helsley trailing just behind, leading a third tier of closers that features Pete Fairbanks, Kyle Finnegan, Emilio Pagan, and Kenley Jansen.

Helsley is the one guy out of the group who really should belong at the top of the market, if you ignore what happened after the trade.

Across seven seasons with the Cardinals, Helsley pitched to a 2.67 ERA, and in 2024, Helsley led all of baseball with 49 saves, pitching to a 2.04 ERA. It was part of a three-year stretch where Helsley never finished with an ERA over 2.45.

If Helsley had free agency after the 2024 season, we would legitimately be looking at a closer who could push for something close to the five-year, $95 million deal Josh Hader signed a few years ago with the Houston Astros.

Instead, the Orioles are able to land Helsley on a two-year, $28 million deal, which checks in just below what Raisel Iglesias just signed on a one-year deal in terms of AAV.

If Helsley were to take a straight one-year deal, he likely could have gotten that same $16 million, but instead, he takes a shade less to get the pillow of a second-year player option.

There is a risk in this deal for Baltimore, as he could never return to being one of the top closers in baseball, and they would be on the hook if he has a bad year in 2026. If he has a good year, he’s gone.

Still, if giving a second year gets the deal done, the Orioles were wise to give it to Helsley, as he has as much upside as any of the top relievers on the market. Helsley may have been hit hard with the Mets, but he was still throwing hard, and he pitched to a 3.00 ERA prior to the trade.

If the Orioles get the guy the Cardinals had across his last three and a half seasons with the team prior to the deadline, they are getting one of the best closers in the game.

Free Agent Closers Stats From 2022 through 7/31/2025

Before getting traded to the Mets, Helsley was leading all impending free agents in ERA and saves, while being in second in innings pitched, and third in FIP and strikeout rate.

Again, Helsley was looking at signing at least a four-year deal, which could have paid him as much as $20 million per season. Now, he is forced to take a prove-it deal. But one where he can return to pitching in the ninth inning, where he can re-establish himself as one of the best closers in the game.