Gerrit Cole Trade, 2018
Another recent instance where the Yankees were viewed as favorites from the second a player hit the market, only to hem and haw over whether or not to include Underwhelming Talent A or Failed Prospect B before a rival stepped in and finished the deal.
The Yanks were "in the lead" for a Gerrit Cole trade with the Pirates after the 2017 season for quite a while, but couldn't figure out a package led by either Clint Frazier or Miguel Andújar. Who knows whether the Pirates wanted one, both, or neither, but eventually the Astros got the job done with a Joe Musgrove/Colin Moran-fronted package.
Musgrove didn't figure it all out until leaving the Pirates, while Cole had one of the best pitching seasons in recent history for the 2019 Astros (20-5, 2.50 ERA, 326 Ks in 212.1 innings). He also turned the tide on the 2019 Yankees with his gutsy Game 3 ALCS start in the afternoon sun at Yankee Stadium, earning a mega-deal in New York a few months later.
Pitching with the Yankees had always been his dream. Imagine how incredible it would've been to secure those two additional prime years and toss Monster Cole in Game 1 of the 2018 ALDS at Fenway instead of JA Happ?