It is possible and maybe probable that Kevin Reese has the most challenging job inside the Yankees’ front office.
“I’m not sure I’d say that,” Reese said with a smile.
We’ll say it for him. The Yankees’ vice president of player development is in charge of consistently turning prospects into ammunition for GM Brian Cashman, either through trade (most of the time) or through major league promotion (less often).
No team has traded more prospects this decade than the Yankees, whose championship-or-bust mentality means the farm system is more of a trade-deadline resource than an asset for frequent promotions. Last July 31, Cashman tapped into Reese’s system and converted 11 prospects into David Bednar, Jake Bird, José Caballero and Camilo Doval. A relatively quiet 2024 deadline that imported Jazz Chisholm Jr., Mark Leiter Jr. and Enyel De Los Santos still cost six prospects. From the 2022 trade deadline through the December 2023 Juan Soto trade, the Yankees traded 16 pitchers — 15 prospect types plus Michael King — along with several position players in all-in swaps that did not ultimately pay off.
