Andres Chavez
For every major league team, the final week of March feels like a high-stakes game of musical chairs. The New York Yankees are no different. While the stars already have their names etched into the lineup card, the periphery of the roster remains a blurry puzzle.
We know that Aaron Judge, Jazz Chisholm, Max Fried, or Cam Schlittler will be on it, but nobody has a clue whether they will take Oswaldo Cabrera, Randal Grichuk, or Max Schuemann, or if they will break camp with Cade Winquest, Jake Bird, or Brent Headrick.
The Bullpen Shakedown
The real drama, however, is unfolding in the bullpen. The Yankees recently decided to move on from Angel Chivilli, who was brought in as a project but couldn’t quite find his best command during his audition. His departure has thinned the herd, leaving a handful of arms—Bird, Winquest, Headrick, Kervin Castro, and Yerry De Los Santos—vying for the last one or two seats on the plane to Opening Day.
In this environment, every relief appearance is like a final exam where you aren’t allowed to use a pencil. One bad outing can erase weeks of good work, yet the Yankees seem to be looking past the raw box scores for one specific candidate.
Taking a Chance on Cade Winquest
According to Greg Joyce of the New York Post, the wind is blowing in a specific direction: Cade Winquest. While nothing is set in stone yet, manager Aaron Boone recently spoke about the Rule 5 pick with the kind of optimism that usually precedes a roster spot. Boone noted that Winquest has shown enough in camp and called him a good pitcher.
Keeping a Rule 5 pick is always a bit like adopting a high-energy puppy; you see the potential for a great companion, but you know there might be some messes to clean up early on.
Because of the draft rules, the Yankees can’t simply stash Winquest in the minors for seasoning. If they want to keep him, he has to stay on the active roster, or they risk losing him back to the Cardinals.
Potential Over Performance
On paper, Winquest is a bit of an enigma. He spent 2025 navigating High-A and Double-A, putting up a respectable 3.99 ERA over 106 innings. However, at nearly 26 years old, he hasn’t yet tasted Triple-A, and his spring training has been rocky, to say the least.
An ERA of 6.48 over eight-plus innings isn’t exactly a resume-builder, and scouts point out that his fastball isn’t the kind of “blown-by-you” heat typical of modern relievers.
So why the interest? The Yankees’ brass believes in the overall package, one that also includes a sinker, a curveball, a sweeper, and a changeup. They see a pitcher who doesn’t blink when the lights get bright, believing his secondary pitches and mound presence will translate better than the spring stats suggest. It is a gamble on raw traits over recent results, a leap of faith that the “stuff” will eventually catch up to the stage.
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