Carlos Correa (on a one-year deal!), 2021-22 offseason
Passing on Seager was egregious, but if you account for the way the Yankees think/their reticence around plopping 10 years on any player, declining Carlos Correa's overtures last offseason was even worse.
Why? New York was so opposed to getting involved in free agency that they instead "thought outside the box" long and hard until they came up with an Isiah Kiner-Falefa/Josh Donaldson stopgap duo. By trading for those two Twins, they freed up enough money for Minnesota to sign ... Correa! To a deal with an opt-out after Year 1 that was always destined to become a one-season wonder (it did).
The Yankees were too impatient to wait around until Correa required only a one-year commitment. They were also too silly to listen to the shortstop, who tried to engage New York in both 2022 and 2023 before he signed with the Giants/Mets/Twins again.
Not sure anyone is comfortable with Correa's next six years, but if he was actively seeking a "one-year deal" during the winter of 2021-22, the Yankees should've engaged rather than facilitated his move to the AL Central. Even a "down year" for Correa (4.4 fWAR) could've paid dividends as New York ran out of gas and was eliminated by Houston. You don't think he might've had a little fun playing them?