Feb 13, 2026; Tampa, FL, USA; New York Yankees pitcher Cade Winquest (80) works out during spring training practices at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images Kim Klement Neitzel-Imagn Images

Rule 5 Draft Leaves Yankees With Interesting Bullpen Decision

Originally posted on New York Yankees on SI
By Jordon Lawrenz | Last updated Feb 28, 2026 1:00 PM ET

With under a month go to until the New York Yankees must set their Opening Day roster, they still have a few reliever spots up for grabs.

There are clear locks like David Bednar and Camilo Doval, but most projections believe Cade Winquest will make the Opening Day roster.

Knowing he was the Yankees Rule 5 draft pick in 2025, this makes complete sense. Even though he's yet to make his big league debut, the Yankees would need to send him back to the St. Louis Cardinals should they opt to go with a different reliever in his place.

It's been quite some time since the Yankees had a Rule 5 draft pick stay in the big leagues the entire season, but that doesn't mean they can't at least give Winquest a look to start the year.

Yankees Can't Lose Winquest Without Giving Him a Shot

Here's a look at Rule 5 Draft pick Cade Winquest.

The bullpen hopeful told me that he's added a sinker to his arsenal and is happy with the pitch's development thus far. #Yankees pic.twitter.com/pllyv1foeQ
— Gary Phillips (@GaryHPhillips) February 12, 2026

The Yankees haven't made a selection in the major-league phase of the Rule 5 in 14 years, so bringing in Winquest was a big move. They have a ton of confidence in the 25-year old and one of the main benefits of bringing him in was the fact that he's a right-handed pitcher.

As silly as that sounds, his greatest competition is lefty Brent Headrick. The 28-year old threw 17 games for the Yankees last year and finished with a 3.13 ERA. He performed quote well in his 23 innings, but the team can move him around far easier than they can with Winquest.

Knowing the Yankees went out of their way to draft the Texas native, it doesn't seem right to only judge him off his Spring Training performances. He could easily come to the Big Leagues and not perform well, and that's okay, but Winquest has a chance to be the first pick to stay an entire season since Billy Parker in 1973.

Yankees Have LIked Winquest Since 2022 Draft

Rule 5 pick Cade Winquest kept his push for a Yankees bullpen spot going with a scoreless outing today.

The cut-ride fastball looks really good! pic.twitter.com/HLuWOEvmGs
— Pitch Profiler (@pitchprofiler) February 26, 2026

This pick has been years in the making so it's hard to imagine a scenario where the team decides not to put Winquest on the Opening Day roster. It's certainly a possibility, and a few dreadful showings next month will go a long way, but still, he should get the nod over a guy like Headrick.

Winquest went 5-7 last year with a 3.99 ERA. He started 23 of the 25 games he appeared in, but the Yankees starting rotation is already locked into place. Moving him to the bullpen could be a career-saving move, and it's something the Yankees have to at least attempt before they send him back to St. Louis.

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This article first appeared on New York Yankees on SI and was syndicated with permission.

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