Important (and troubling) layer of Yankees' 2025 trade deadline is being ignored

There was a lot to like about the New York Yankees' trade deadline performance. The club addressed clear needs; filling a massive hole at the hot corner, revamping the bullpen on the fly, and fortifying the bench with some legitimately useful role players and depth options.

That has led many to proclaim that they are one of the deadline's big winners, even if we're still not convinced that Jake Bird was a necessary addition. Perhaps the best part of the deadline, though, was the restraint general manager Brian Cashman showed, holding on to top prospects like Spencer Jones and George Lombard Jr. while making several moves that significantly improved the club.

However, two of the more minor deals that the longtime Yankee boss pushed across the finish line show the dark side of that prospect-hugging strategy, and are an overlooked aspect of where the Yankees have fallen short over the years when it comes to navigating the trade market.

The Yankees' lesser deadline deals highlight an ongoing problem with the organization's approach to the trade market

If someone asked rival executives a few years ago what the Yankees could have swapped Oswald Peraza and Everson Pereira for, the answers would have been much more than an 18-year-old outfielder who is struggling to hit in the Dominican Summer League and light-hitting utilityman Jose Caballero.

After an impressive cup of coffee in 2022 that saw him slash .306/.404/.429, Peraza topped out at No. 52 on MLB.com's Top 100 prospects list in 2023. That same year, Pereira seemed to have all the makings of a five-tool player and was ranked the sixth-best prospect in the Yankees' system.

At that point in time, either player could have served as the centerpiece for a blockbuster deal, but Cashman's desire to horde prospects took them off the table. A severe failure in development plans for both once-promising youngsters saw their value steadily plummet while the organization squeezed them out in favor of other youngsters, specifically Anthony Volpe and Jasson Dominguez, who blocked pathways for Peraza and Pereira.

Two years later, the club finally decided to cut bait with two players who they'd known for a long while weren't part of their future plans, letting any value they had evaporate in the process.

This is not a new phenomenon for Cashman and the Yankees. Remember how they refused to move Phil Hughes and Melky Cabrera for Johan Santana at a time when Santana was the best pitcher in baseball? In the case of Hughes, the organization then did everything in its power to stunt his development. Ring a bell?

Similar things can be said for the likes of Jesus Montero, Gary Sanchez, Greg Bird, Joba Chamberlain, and many others throughout the years. All of whom were either held on to until their value had cratered to the point of no return, and/or had their development screwed up so badly that any impact they could have made would become a pipedream.

The Peraza and Pereira trades then bring to light three key issues with how the Yankees operate when it comes to trading their most talented youngsters for proven big league talent. First, there's a fear of moving a highly-touted youngster for star big leaguers that is far too common within the organization. Second, there's a hesitancy to pull the trigger on a deal even when the club knows that the prospect in question is likely not in their future plans. And third, the organization has built up a rigidity in its decisions regarding the future at the cost of developing talented prospects whose pathway to a consistent major league role might not be readily apparent.

It has become commonplace for Brian Cashman to try to have his cake and eat it when it comes to navigating his top prospects' value on the trade market, and often in his quest to look like the smartest guy in the room, he ends up with egg on his face. The Peraza and Pereira deals are just two more examples of this lack of strategy.