6 players since 2020 the Yankees should have traded before their value tanked

Over the last few decades, the New York Yankees have had a love-hate relationship with their prospects. The last great Yankee Dynasty of the late 90s was built on the backs of the farm system, with the Core Four getting top billing and other homegrown pieces playing prominent roles.

That gave way to a star-chasing mentality throughout the 2000s, which squeezed the majority of top prospects out of the system via high-profile trades and big-name free-agent signings. The failings of those star-studded teams gave way to a renewed focus on the farm system in the mid-2010s, which has continued on in some form to the present day.

The Yankees of the 2020s don't necessarily shy away from the big money contracts, but they have become much more judicious in how willing they are to part with top prospects in exchange for star-caliber players on the trade market. Unfortunately, they haven't always followed through on developing those prospects, in some cases betting on the wrong player, and have seen the perception of many highly-touted youngsters plummet as their value turns to dust.

6 players since 2020 the Yankees should have traded before their value tanked

Oswald Peraza

Believe it or not, there was a time when the Yankees looked to have not one, but two future star shortstops. Oswaldo Peraza and Anthony Volpe were both top-100 prospects, and while only Volpe remains on the Yankees' roster, it's more than a stretch to say that future stardom is in the cards for either.

Peraza topped out at No. 52 on the top 100 in 2023, thanks to his impressive 2022 debut when he hit .306/.404/.429 over 18 games. For some reason, the club pushed him aside in favor of Volpe in 2023, even as the higher-ranked Volpe struggled with his first taste of big league action. From that point forward, Peraza was used sparingly until this season when he was pressed into action after Oswaldo Cabrera's gruesome injury.

Unfortunately, by that point, the damage was already done. With his confidence shot and his development completely stunted, Peraza's 25 wRC+ ranks dead last among big league hitters with at least 170 plate appearances in 2025. The 25-year-old went from a prospect valued by many evaluators who would have had a ton of trade value after his impressive 2022 debut to a player who was jettisoned for a teenage outfielder who is struggling to make contact in the Dominican Summer League.

Peraza should have been traded the moment the Yankees decided to anoint Volpe as the shortstop of the future; instead, they held on for years too long until nearly all of his value had melted away like an ice cream cone in the hot summer sun.

Everson Pereira

Signed out of Venezuela for $1.5 million as an international amateur free agent, Everson Pereira ranked No. four overall in his class, projecting as a potential five-tool player in center field.

As the years went on, Pereira's frame filled out and his power projections increased at a slight cost to his hit tool, but still seemed to have a well-rounded game that would allow him to flourish one day in the big leagues. Since turning pro, Pereira mashed at every stop in the minor leagues despite an elevated strikeout rate.

The youngster reached Triple-A in 2023, posting a .300/.373/.548 line at the level which earned him a call up to the bigs on August 23 to play left field, a position where the Yankees had run through a wholly uninspiring cast of characters.

Pereira would get 27 games of runway down the stretch, hitting a pitiful .151/.233/.194 over 103 plate appearances and striking out a ghastly 38.8% of the time as the Yankees continued to collapse and finished the year with a disappointing 82-80 record.

Pereira would continue to mash in Triple-A throughout 2024 and 2025 up until he was dealt at this year's deadline for light-hitting utilityman Jose Caballero. One has to wonder if the Yankees hadn't punted on the 2023 deadline and instead had used Pereira as a chip to fill one of their multitude of needs, things might've worked out differently.

Instead, they let Pereira get exposed as a 22-year-old and never gave him another shot to rebuild his value, ultimately ruining whatever remained of the flawed-but-toolsy outfielder had on the trade market.

Austin Wells

The Yankees have garnered a reputation over the years for successfully developing two things in their minor league system: pitchers and catchers. The club identified early on that it believed Austin Wells was the jewel of its catching riches, intentionally clearing a pathway for the bat-first youngster to claim his spot behind the dish.

This past offseason, the Yankees cleared the final hurdle for Wells, dealing veteran backstop Jose Trevino, who had previously shared the starting role with Wells, to ensure that the former top-100 prospect was given free rein behind the dish.

In a way, it made sense. Wells made big strides to become viable defensively in 2024, and while his power hadn't yet fully translated, the lefty-swinging catcher had posted a stellar 11.4% walk rate. However, 2025 has become a different story entirely. His walk rate has been nearly cut in half, the strikeouts are increasing, the power is inconsistent, and all of the gains made defensively have been given back.

Meanwhile, the Yankees have all but locked themselves into Wells. They also dealt rookie sensation Carlos Narvaez in the offseason. Agustin Ramirez was traded for Jazz Chisholm Jr. last season and recently showed the Yankees exactly what they're missing out on. Top catching prospects Rafael Flores and Edgleen Perez just went to Pittsburgh in the David Bednar deal.

Like it or not, the Yankees are married to Wells for the foreseeable future, but if they were to trade him, his value is now at an all-time low. It's likely that not too long ago, he could've fetched more than any of these aforementioned youngsters on the trade market, and one has to wonder if the Yankees would have been better off betting on a different young backstop.

Anthony Volpe

Prior to exhausting his prospect status in 2023, Anthony Volpe was the No. 5 overall prospect in all of baseball. At 22 years old, he could have been dealt in a package that would have returned nearly any star available on the trade market. Instead, the Yankees anointed him as the starting shortstop, a coronation that was years in the making.

As a rookie, Volpe struggled at times, underwhelming with the bat but looking mostly serviceable with the glove, even if some of his decisions were shaky at times. The thought was the bat would come around with experience, and the glove would get better as he got more comfortable tapping into his lauded baseball IQ.

Now in 2025, we're still in the same spot with Volpe, who has become one of the most polarizing Yankees in recent memory. There have been pockets of production that make you think it's finally clicked for the 24-year-old, but the overall body of work paints a picture of stagnation and, at times, regression.

This is the player who caused the Yankees to pass over many star free agent shortstops. This is the man responsible for subjecting fans to a year of Isiah Kiner-Falefa starting at shortstop because he was simply too valuable to block. To put it bluntly, Volpe is currently a below-average starting shortstop, and despite his youth and pedigree, that represents a stark drop-off in value that begs the question: would the Yankees have been better off trading him?

Estevan Florial

Estevan Florial, in some ways, was Everson Pereira before Everson Pereira came to be. An athletic and powerful outfielder who signed as a teenager, Florial always had more questions about his hit tool than Pereira, but otherwise could have listed a number of similar strengths.

Florial struggled once he first reached the upper levels of the minor leagues, but seemed to begin to turn a corner in 2022 when he slashed .283/.368/.481 with 15 homers and 39 steals at Triple-A as a 24-year-old (though he struck out at a very concerning 30.4% rate).

He'd be traded ahead of the 2024 season in exchange for minor league depth arm Cody Morris, a disappointing return for a once very exciting prospect. Florial is currently toiling away in the KBO, waiting for his next opportunity.

Deivi Garcia

The Yankees' third overall prospect in 2020, Deivi Garcia showed a lot of promise thanks to a devastating curveball, high-spin fastball, and promising changeup. Garcia would make his big league debut in 2020 as a 21-year-old in large part due to the cancellation of the minor league season as a result of the COVID-19 pandemic.

While Garcia mostly struggled in the six starts he made that season, there were enough promising moments to hold out hope. Unfortunately, he'd never reach the same levels in the minors following that brief big league exposure, and by 2023 he was disappointingly put on waivers and claimed by the Chicago White Sox.

The bottom fell out pretty quickly for Garcia, but for a time he had some legitimate value on the trade market, which was ultimately squandered.