The New York Yankees saw their 2025 season end thanks to a lack of offense and a struggling pitching staff. After falling to the Toronto Blue Jays, there are a lot of decisions the Yankees need to make in the offseason.
One of those decisions will revolve around top prospect Spencer Jones. Do the Yankees move on from him for an MLB-ready talent, or hold onto Jones in hopes of positive development?
The Yankees, back in 2022, were faced with a similar decision with Anthony Volpe. And according to Ryan Garcia of empiresportsmedia.com, the Yankees turned down two trades to keep Volpe. Both of those moves would've been great pickups for the Yankees in both the short and long term.
The Yankees turned down two good Anthony Volpe trades
"When Anthony Volpe was a prospect," Garcia writes, "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."
The Yankees passed on trading Volpe, who went on to have major defensive struggles on top of lackluster offensive production in the second half of the 2025 MLB season.
While they couldn't predict Volpe's development at the time, it's hard to ignore the massive missed opportunity these two trades present.
For starters, Castillo has been one of the better pitchers in baseball since the start of the 2022 season. Across the 120 games he's started, Castillo has a 3.39 ERA, 11.0 bWAR, and 723 strikeouts.
He was an All-Star for the Mariners in 2023, putting up a 3.34 ERA in 33 starts, along with being an All-Star with the Cincinnati Reds in the first half of 2022, thanks to a 2.86 ERA in 14 starts.
The Yankees needed more starting pitching this past season, and Castillo's 3.54 ERA in 32 starts and a 3.24 ERA in two postseason starts would've been a nice addition for the Yankees' rotation.
Olson, on the other hand, might be an even worse miss. The Atlanta Braves acquired Olson in 2022, and since joining the Braves, he's been one of the best sluggers in baseball.
Across Olson's four seasons since 2022, he's put up 20.8 bWAR with 146 home runs, 341 RBIs with a.261 batting average, and an.859 OPS. Olson was named to two All-Star Teams in 2023 and 2025, and led the National League in doubles with 41 in 2025.
But his most impressive feat was his MLB-leading 54 home runs and 139 RBIs in 2023 en route to a fourth-place MVP finish in the NL. A slugger like Olson would've been a huge pickup for the Yankees' offense.
While it was impossible to know at the time the development of Volpe, Olson, and Castillo, this report highlights the missed opportunity that Volpe's present so far through his MLB career.
Volpe hasn't been a terrible player, but he's not lived up to the potential he was ascribed. Passing on these two trades only makes Volpe's development look a lot worse, as the Yankees instead could've had another ace pitcher or an elite slugger if they parted with Volpe back in 2022.
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