Brian Cashman's response to Cade Winquest move is sure to enrage Yankees fans

Given how things ended with the Cade Winquest experiment, it became abundantly clear why, prior to last December, the Yankees hadn't made a Rule 5 draft selection for 14 years. The vast majority of these guys are extremely raw players, and the restrictions imposed on their roster maneuverability make it nearly impossible to compete and develop one of them while they occupy a 26-man roster spot.

Brian Cashman made it clear the Yankees didn't regret the decision to move on to Winquest before he even threw a big league pitch, but his feelings were a bit more complicated than that.

“We were forced to make a decision and ultimately, he hadn’t even pitched yet this year,” Cashman said before the Yankees’ April 10 loss to the Rays. “It didn’t work out the way ultimately we wanted. But he’s really talented. We like the process we went through when we selected him, but it would have been nice to be able to find room to get him into games to develop, but it’s hard when you’re trying to compete to develop at the same time. So it just didn’t play out the way we wanted it to. We think he’s got upside, he’s just going to need some time.”

Brian Cashman's explanation for Cade Winquest debacle ignores Yankees' bullpen problem

Aaron Boone noted that before the Winquest DFA and subsequent return to the Cardinals, the 26-year-old right-hander was "a batter away" from appearing in a game four or five times, but it never came to fruition.

That's insanity. The Yankees paid $100K to acquire Winquest, which to them is a drop in the bucket. But they used a real asset on him — a big league roster spot. Not finding a way to work him into a game at least one time to see if you had anything at that point is just malpractice. Not to mention, it came at the cost of burning a number of other relievers in the early going.

It also brings into question the whole thought process. Both Cashman and Boone spoke highly of his talent, but he came in with just 42 1/3 innings pitched above High-A, all of which came in 2025 for the Cardinals' Double-A affiliate. If we're being honest, what was the probability that this worked out in any way, shape, or form? Infinitesimal.

It's also hypocritical. While they have more big league experience, the Yankees have tried the diamond-in-the-rough strategy plenty of times, with trades for relievers like Jake Bird and Angel Chivilli serving as prime examples. Neither of these examples received much run, but they both got a shot to prove themselves at minimum.

Cashman needs to understand that a team in the Yankees' position can't afford to continuously waste assets on unproven bullpen commodities. You want to sign a minor league free agent like Brent Headrick and develop him, that's fine. It's even smart, and they might have another potential weapon waiting in the wings in Yovanny Cruz, who was acquired in a similar fashion.

This isn't to say that New York needs to consistently sign big-ticket relievers to fill every role in their bullpen. There are plenty of quality veterans with track records who can fill the middle innings at affordable prices. Those are the pitchers they should be targeting for major league jobs.

Cashman said it himself. It's hard to compete and develop at the same time. So stop trying to do it. Use your minor league system to develop players. Put the finished products on the big league roster. It's not complicated unless you make it so.

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