2. Michael King
The Yankees are currently in the process of stretching out King to be a starting pitcher. But a starting pitcher for whom?
New York's bullpen depth chart, even if you include Holmes, looks fairly barren next season after the team managed to create a strength in the back end over the past half-decade. Jonathan Loaisiga, oft-injured, is one of the roster's few "sure things." Wandy Peralta will enter free agency, Tommy Kahnle has struggled with high-leverage appearances this summer (and is an eternal injury risk), and King seems poised to be something in between a starter and reliever.
He believes starting should be his full-time destiny, and while it's hard to argue with the stuff, Yankee fans have plenty experience with pitchers being jerked between the rotation and bullpen and getting lost along the way.
King's potential journey toward being a trade asset rather than a Yankees stalwart depends largely on how this role change goes. The Yankees will absolutely need insurance in the rotation next year, and if they end September believing King can provide it, he'll stay. If they determine that he's a reliever and only a reliever moving forward, they should probably be the ones receiving a haul for his services rather than paying a heavy prospect cost for a similar pitcher with two years of control. King's locked down through 2024 and 2025, which seems poised to be a highly uncertain period for this Yankees franchise. They should at least entertain moving him.