After a difficult 2025 season, two-time All-Star Ryan Helsley is officially on the free-agent market. The hard-throwing right-hander looked sharp during the first half of the year with the St. Louis Cardinals, but things unraveled after he was traded to the New York Mets at the deadline.
But despite the brutal stretch, teams know exactly what he’s capable of when he’s right. He wasn’t far removed from anchoring the Cardinals’ bullpen, earning multiple All-Star nods and taking home National League Reliever of the Year honors.
With the Winter Meetings approaching and free-agent activity set to ramp up, Helsley stands out as one of the more intriguing rebound candidates on the relief market. Here are two teams that make the most sense for the 31-year-old flamethrower.
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Boston Red Sox
Sep 30, 2025; Bronx, New York, USA; Boston Red Sox pitcher Aroldis Chapman (44) pitches against New York Yankees during the bottom of the ninth inning during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images
The Red Sox just watched Aroldis Chapman turn in a dominant season as their top bullpen weapon—but with Chapman now a free agent, there’s no guarantee he returns to Fenway Park. Boston can’t afford to enter 2026 without a fallback plan, and Helsley fits the mold of the type of upside play they’ve taken chances on before.
Helsley brings elite fastball velocity, late-inning experience, and the kind of strikeout potential that mirrors what Chapman gave them. If the Red Sox are looking for a Plan B with closer-level stuff, Helsley offers that at a likely affordable price.
A short-term “prove-it” contract similar to the one Boston gave Chapman last offseason could work well for both sides. The Red Sox would stabilize the back end of their bullpen, and Helsley would get the chance to rebuild his value in a competitive environment—while helping Boston stay in the playoff hunt in a stacked American League East.
St. Louis Cardinals
Jul 24, 2025; St. Louis, Missouri, USA; St. Louis Cardinals relief pitcher Ryan Helsley (56) celebrates after the Cardinals defeated the San Diego Padres at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images | Jeff Curry-Imagn Images
A reunion might make even more sense.
The Cardinals are entering a soft rebuild under Chaim Bloom and aren’t expected to spend big this winter. That makes low-cost, upside veteran relievers an ideal target—exactly the type of move Bloom loves. Helsley, drafted by St. Louis in 2015 and a Cardinal until his 2025 trade, checks every box.
He’s also open to the idea. On the “Cardinal Territory” podcast, Helsley said he expects his former team to give him a call. After his Mets struggles, St. Louis wouldn’t need to break the bank to bring him back, and he’d return to a familiar setting where he’s had his greatest success.
Fans remember that Helsley saved a franchise-record 49 games in 2024. Bringing him back on a low-risk deal makes perfect sense for a team trying to focus on the future, but also make some improvements.
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