TAMPA, Fla. — The New York Yankees came into spring training this year with most of their 26-man roster already sorted out. The starting lineup was largely set. The rotation had its top five penciled in. But at least one question lingered as Grapefruit League games kicked off in February: Who would fill the final spots in the bullpen?
After losing closers Luke Weaver and Devin Williams to the crosstown Mets in free agency, the Yankees opted against splashing for big-name replacements. Instead, they doubled down on internal competition. A handful of arms were told they would have a shot to earn a roster spot in camp.
And if you listen closely to Yankees manager Aaron Boone, it sounds like one pitcher has separated himself from the pack.
From waiver claim to bullpen weapon
His path to the Yankees was anything but conventional. The club claimed him off waivers from the Minnesota Twins in February 2025. A ninth-round pick out of Illinois State in the 2019 MLB Draft, the Braidwood, Illinois, native had spent most of his minor league career as a starter. Brent Headrick converted to full-time relief after arriving in the Yankees organization.
The transition paid off. The 6-foot-6 southpaw made 17 appearances for the Yankees in 2025 and threw 23 innings. He posted a 3.13 ERA with a 32.6% strikeout rate and a 7.6% walk rate. His fastball averaged 94 mph and touched as high as 97.1 mph, giving the Yankees bullpen a rare power arm from the left side.
Velocity consistency was the one area that needed work. Boone noted earlier this spring that Headrick’s stuff would fluctuate from outing to outing during his first Yankees season.
“Last year, we were probably searching for that. He’d pitch well, and you’d see the bump up in stuff,” Boone said.
Headrick has said he spent the winter training specifically for the Yankees’ bullpen role, and he believes his body is better prepared this time around.
“By the end of the season, the body had fully adjusted, and I felt like I was ready for the bullpen role,” Headrick said.
Boone makes his feelings clear on Headrick
While Boone has been diplomatic about most of the candidates, he has not been shy about one name: Brent Headrick.
Per Greg Joyce of the New York Post, Boone said at the end of February, “I’m pretty high on him,” when asked about the 28-year-old left-hander. More recently, Gary Phillips of the New York Daily News reported that Boone called Headrick flat-out “legit.”
“I think he’s legit,” Boone said.
Those are not the kind of words a Yankees manager tosses around casually in mid-March, especially with roster decisions days away. When a skipper repeatedly singles out the same pitcher over multiple weeks to multiple reporters, the message is hard to miss for anyone tracking the Yankees’ bullpen race.
Headrick’s spring numbers back up the praise. Through mid-March, he has racked up nine strikeouts against zero walks in 4 2/3 innings of work. His 3.86 ERA does not fully capture the swing-and-miss dominance he has shown in camp.
A different kind of lefty for the Yankees’ pen
If Headrick does land on the Yankees’ Opening Day roster, the club would carry three left-handed relievers alongside Hill and Yarbrough. But Headrick would offer something neither of those veterans brings.
Hill relies on a funky delivery and a diving sinker to generate ground balls. Yarbrough is a soft-tossing innings eater who can fill in as a spot starter. Headrick, on the other hand, regularly sits between 94 and 96 mph and brings pure strikeout ability. He also features a tight slider that tunnels well off his fastball and has added a sinker to attack left-handed hitters inside.
That combination of power and swing-and-miss stuff from the left side is something the Yankees bullpen has lacked in recent years. His 34.1% whiff rate in 2025 ranked among the best on the Yankees’ pitching staff.
Five fighting for the Yankees’ last bullpen spot
The Yankees entered camp believing they had roughly two bullpen spots to fill behind a core of David Bednar, Camilo Doval, Fernando Cruz, Tim Hill, Ryan Yarbrough, and Paul Blackburn.
Chivilli has been hit hard, posting a 14.29 ERA in Grapefruit League action that has all but knocked him from contention.
Castro has been the most dominant pitcher in the group. He has thrown seven shutout innings over five Grapefruit League outings for the Yankees and arguably deserves a spot. But Castro can be optioned to the minors. The Yankees may prefer to keep a pitcher who cannot be sent down without consequences.
This is where Bido and Winquest become co-favorites. Neither can be optioned, which means the Yankees would have to risk losing them if they do not make the roster.
Bido, a Feb. 5 waiver claim from the Angels, has allowed one run in four innings across four Yankees spring outings. He brings 58 games of MLB experience over the last three seasons. That track record matters in a bullpen where trust is everything in high-leverage situations.
Rule 5 pick Winquest has never pitched above Double-A. His Grapefruit League numbers have been rough, with a 5.68 ERA over six outings for the Yankees. But he threw a scoreless inning with a hit batter against the Tigers on Thursday. If the Bombers do not keep him on the 26-man roster, they must offer him back to St. Louis.
Jake Bird entered camp as a favorite for a Yankees bullpen spot. He has not pitched like one. The right-hander has posted a 4.50 ERA with three walks in six innings across six spring outings. The command has been inconsistent.
Bird can be optioned, which puts him in the same category as Castro. If the Yankees choose roster flexibility over spring performance, Bird could start the year at Triple-A.
De los Santos has been sharp, allowing no runs in 4.2 innings over four games for the Yankees. Like Castro, he has major league experience and will likely factor into the New York bullpen at some point in 2026. But his option status makes him an Opening Day long shot.
Boone acknowledged that results across the board have been mixed.
“Frankly, we’ve had some mixed results for those guys in the mix for those last two spots, so we need to see that play out a little bit,” Boone said.
For now, Headrick appears to have the inside track. Among all the contenders for the final Yankees bullpen spot, he has posted the best numbers, earned the loudest praise from his manager, and brings a skill set no one else in the Yankees organization can match. Barring a sudden reversal in the final days of camp, the former waiver claim looks poised to break north with the Yankees when the club opens the 2026 season.
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