Inside The Pinstripes

Yankees Explain Historic Rule 5 Draft Pick

The New York Yankees made their first move in the Rule 5 Draft since 2011, and the staff recently explained why.
Erin Shapland|
Aug 4, 2025; Arlington, Texas, USA; A view of a New York Yankees helmet and logo before the game between the Texas Rangers and the New York Yankees at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images
Aug 4, 2025; Arlington, Texas, USA; A view of a New York Yankees helmet and logo before the game between the Texas Rangers and the New York Yankees at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | Jerome Miron-Imagn Images

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New York Yankees

The New York Yankees' first Rule 5 Draft pick since 2011 came this year, when they picked up right-handed pitcher Cade Winquest from the St. Louis Cardinals organization.

Winquest himself was blown away by the move.

“I couldn’t talk for probably a good hour. I didn’t know what to think at first,” Winquest said via MLB's Bryan Hoch. “I had to call my agent to make sure this was real, and then I went and called my parents and family. We were all pretty shocked. It was obviously a really cool moment. It’s still a rush, thinking about it.”

Yankees assistant general manager Michael Fishman described what the club sees in Winquest, which aligns with their current offseason pitching concerns. The aging rotation is injured at the moment, and with a couple other under-proven young arms, Winquest may not be far off from being very useful.

"He's got big velocity," Fishman said. "He has characteristics that our pitching group is good at working with. We'll get him with our pitching department and make a few tweaks. He's somebody who hopefully could help us."

Winquest's Performance in the Minors

Winquest, 25, logged a 3.99 ERA across 25 appearances (23 starts) in 2025 with two teams; he was promoted from High-A to Double A in July. 6-foot-2, 205 lbs, Winquest was selected in the eighth round of the 2022 draft. The Yankees had intended to select Winquest in the draft after selecting current starting pitcher Cam Schlittler, but the Cardinals beat them to him.

Winquest recounted a conversation with pitching coach Matt Blake following the draft, where Blake told him that their interest stemmed from his ability to spin the ball.

“From what I’ve been told, it’s my ability to spin the ball,” Winquest said. “With my fastball and curveball, I have really good spin on that. Even with my other pitches, I’ve been able to pick up pitches fairly quickly and use that to my advantage."

New York Yankees pitcher Will Warren (98) with New York Yankees pitching coach Matt Blake (77)
May 14, 2025; Seattle, Washington, USA; New York Yankees pitcher Will Warren (98) and New York Yankees catcher J.C. Escarra (25) wait on the mound to talk with New York Yankees pitching coach Matt Blake (77) during the third inning against the Seattle Mariners at T-Mobile Park. Mandatory Credit: John Froschauer-Imagn Images | John Froschauer-Imagn Images

“What Blake told me was, ‘We love the way you [have] spin capacity on all your pitches.’ He’s really excited to work with me and maybe adjust some grips to make pitches better and maybe add a new pitch. We’ll see.”

The Yankees have made very few moves overall so far this offseason, with Winquest representing the only signing who did not play on the 2025 Yankees so far. They are still, presumably, shopping for a starting pitcher to round out that troublesome early-season rotation, but Winquest represents a promising investment for their near future.

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Erin Shapland
ERIN SHAPLAND

Erin covers the New York Yankees for On SI, reporting on all aspects of the championship chase that comes with a storied franchise. A fan of all storylines, who's looking to bring the latest news and updates to one of professional sports' greatest fanbases.

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