2022: Frankie Montas
And it just keeps getting worse. Anybody gonna get a clue here? Though the jury's still out on the package that went to Oakland in exchange for Montas, the fact the Yankees are going to end up paying him ~$10 million for eight starts is the oversight of all oversights.
Montas, who dealt with a shoulder injury in July of last year (the same one that plagued him down the stretch and eventually needed surgery), was the 2022 deadline's consolation prize behind Luis Castillo. That's how big the gap was.
When the Yankees couldn't get Castillo because of the Mariners' insane overbid, Cashman went for Montas. OK! Sure. Rotation help is great, especially when you can't trust Severino to stay healthy and will have to manage Nestor Cortes' innings as the year progresses.
But wait, that's Brian Cashman's music! The hell is he doin' here?! Cashman, after acquiring Montas to seemingly bolster the rotation to the "next level," went ahead and traded Jordan Montgomery to the St. Louis Cardinals for an injured Harrison Bader, who couldn't suit up until mid-September. Hey, that trade might end up working out, but Cashman's dealings at the deadline completely killed morale and led to the Yankees' horrific slump that nearly saw them choke away a 15-game lead in the division.
As for Montas, he could've have been further from a viable replacement for even Monty! A 6.35 ERA and 1.54 WHIP in eight starts and a meaningless ALCS appearance (one run in one inning) vs Montgomery's 3.11 ERA and 1.08 WHIP in 11 starts with the Cards.
Cashman downgraded and thinned the rotation, acquired an injured player, and will now pay $7.5 million for him to not play in 2023, further derailing the team's pitching plans for this upcoming season.
Really not sure it gets worse than that.