The Bleachers creature almost accepted their fate after their beloved team fell flat against the Toronto Blue Jays in the four-game ALDS. After another season ended familiarly and painfully, it was not rocket science for them to get where they fell short and whose cold streak cost them most in their early playoff elimination after having a good 94-68 regular season.

Anthony Volpe. Yes! The first wave of criticism landed squarely on the 24-year-old shortstop, who had a tough year at the plate and in the field. And then, when the dust had almost settled in as the World Series was just one game away from conclusion in the best-case, a new report from Ryan Garcia of Empire Sports Media just stirred the boiling pot.

The report revealed a stunning piece of the team’s recent history. Garcia wrote, “When Anthony Volpe was a prospect, the team had turned down numerous deals for him, refusing to trade him for Luis Castillo in 2022 or Matt Olson a few months before that.”  This recent revelation suddenly reframes the entire 2025 disappointment.

Anthony Volpe, who was a first-round pick in 2019, exploded in 2021 with a .294 batting average, 27 homers, and 33 steals to become a top-10 prospect in all of baseball.

After that, the Yankees believed in him so much that they held him out of huge trades like Luis Castillo, who had an impressive regular season, and even Matt Olson, who has since hit 146 home runs for the Braves.

But the New Jersey native’s 2025 season was a massive struggle, hitting just .212 with a .663 OPS. Not just the plate, the former Gold Glove made 19 errors, one of the worst marks in baseball. And in the playoffs? His numbers were even worse, with a batting line of .192/.192/.346 with a below-average .538 OPS. Without hitting a go-ahead homer to Boston ace Garret Crochet in the wild card series, he did nothing in the whole playoff scenario in his 26 at-bats in seven appearances.

And the Cincinnati Reds ace, Luis Castillo, who later went to the Seattle Mariners instead, with a 5-year $108M contract, has been a durable star since then, pitching over 550 innings from 2023-2025 since then with less than 4 ERA over all that stint and repeated a back-to-back All-star nod in 2023 as a Mariners. It was the player the Yankees surely miss during a season when Gerrit Cole was entirely unavailable to pitch a single inning.

Since the Yankees passed on those trades, Luis Castillo has anchored Seattle’s rotation with steady sub-4.00 ERAs and multiple All-Star nods, while Matt Olson has become Atlanta’s power engine, blasting over 140 home runs since 2022.

As aggressive teams like the Dodgers and Braves kept reshaping their rosters with bold trades, the Yankees’ caution stood out. Volpe’s 2025 slump was worsened by a partial labrum tear that limited his swing and range, with his barrel rate dropping from 8.3% to 5.9% and exit velocity down nearly two mph. Manager Aaron Boone acknowledged his effort despite the injury, and Brian Cashman reaffirmed his place in the team’s long-term plans.

But this decision was not a one-time thing

The Yankees have long valued homegrown stars — from Jeter and Bernie Williams to Aaron Judge — a philosophy that still shapes Brian Cashman’s cautious trade approach. Unlike bold GMs such as the Dodgers’ Andrew Friedman or the Braves’ Alex Anthopoulos, Cashman often prioritizes keeping prospects over acquiring proven talent.

The Volpe revelation reignited that debate, with Ken Rosenthal noting the Yankees “have missed out on stars by clinging to prospects,” and Jon Heyman adding that Volpe’s struggles “underline the risks of playing it too safe.” Fans echoed similar frustration, calling for a more aggressive front-office mindset.

The Yankees have a history of holding prospects too tightly. It happened when they refused to trade Miguel Andujarr or Clint Frazier for Gerrit Cole in 2018, who they eventually bought with a more lucrative contract later. It happened when they failed to land Cliff Lee in 2010, opting for lesser prospects like Eduardo Nunez or Ivan Nova.

And more recently, they did it with Jasson Dominguez. At the start of the 2025 season, when the market for Kyle Tucker was heating up, the Yankees refused to land him because it would cost them Dominguez.

All of this history puts enormous pressure on the team this winter. So what’s next for Volpe and the Yankees?

Volpe, who played in 2025 with a partial labrum tear, no longer has a guaranteed position on the opening day roster. But for now, he requires surgery and will miss the start of 2026. Trade deadline acquisition Jose Caballero can take his position in the infield. But the outfield also needs a major overhaul.

Cody Bellinger is expected to opt out of his contract. Re-signing him should be a top priority for the team. And another outfielder, Trent Grisham, is also a free agent who had a massive breakthrough season, hitting 34 home runs.

But after a bad postseason, the Yankees can let him walk in this postseason and create a full-time role for Jasson Dominguez. But many fans want the Yankees to aggressively pursue Kyle Tucker to boost the offense at the best possible time, when they have Aaron Judge’s most productive year.

On the pitching side, there is some good news. Gerrit Cole and Clarke Schmidt should return from Tommy John surgery this season, which will help the rotation when Carlos Rodon is going to miss the first few days of the season.