2018: JA Happ
Ohhh MAN! Another extenuating circumstance! Why? Because the trade for Happ actually wasn't bad. The Yankees traded Brandon Drury and Billy McKinney to Toronto in exchange for the left-hander, who went 7-0 with a 2.69 ERA and 1.05 WHIP in 11 starts down the stretch of the 2018 season.
But then came another extension nobody needed. Of course Happ was going to command cash above his actual value after that torrid run and the Yankees took the bait, signing him to a two-year, $34 million contract with a vesting option for a third year. Let's recall how that all unfolded.
Happ finished with a 4.91 ERA, 5.22 FIP and 1.30 WHIP in 31 games (30 starts in 2019). He was the king of surrendering first-inning home runs. More times than not, the Yankees found themselves in a hole when he took the mound. And then came the shortened 2020, which forced the Yankees to dance around his vesting option benchmarks so they wouldn't have to pay him an additional $14 million in 2021. It was an awkward situation nobody wanted.
But here's the grand finale. In Game 2 of the ALDS against the Rays, a series the Yankees led 1-0, New York opted to start Deivi Garcia, who was a pleasant surprise as a rookie that year when the rotation badly needed support. Garcia pitched one inning and the Yankees tried to pull a fast one on the inventors of "pulling a fast one." They used Garcia as an "opener" and planned for Happ, already disgrunted about his contract and very much NOT open to coming out of the bullpen, to piggyback the young right-hander. Happ got destroyed, allowing four earned runs on five hits and three walks in just 2.2 innings of work. The Yankees lost the game, 7-5, and eventually the series. That was the moment it all came crashing down, and every fan with a pulse knew it.
Trade = good. Judgement after the trade = never been worse.