2017: Sonny Gray
Maybe stop trading with the Oakland A's, Brian? Please? Even though Sonny Gray didn't cost much in that 2017 deadline deal ... and even though he pitched five very good innings of one-run ball against the Astros in the ALCS ... this couldn't have been advertised any worse as a failure.
The Yankees needed rotation reinforcements in 2017, but Gray performed more like a back-end starter than a frontline one. He started 11 games, the Yankees lost seven of them. But that was hardly the worst part. Yes, always remember, the story always gets worse when we're talking about stuff like this.
In 2018, Gray couldn't even finish the year in the rotation. And he wasn't used at all in the playoffs. In 30 games (23 starts), the right-hander went 11-9 with a 4.90 ERA, 4.17 FIP and 1.50 WHIP. Aaron Boone's first year on the job. What a joy. He moved Gray to the bullpen in August, which actually improved his 5.56 ERA.
On Aug. 1 of that year, Gray was booed off the mound after allowing seven earned runs on eight hits and two walks in a 7-5 loss against the 47-115 Baltimore Orioles. Gray was smiling as the boos rained down, and that was all she wrote for any support he had among the fanbase.
He was traded to the Cincinnati Reds in the offseason, where he went 23-20 with a 3.49 ERA, 3.57 FIP and 1.15 WHIP in 68 starts. Then he was traded to the Twins before the 2022 season and went 8-5 with a 3.08 ERA, 3.40 FIP and 1.13 WHIP in 24 starts. Always better once they leave.