Keith was asked to pick a player who the Yankees will add this offseason, and a player they will say goodbye to this winter.
For the first part of the prediction, Keith went with a former Yankee who has been a star in the postseason thus far.
“I think there’s no way they don’t get Jordan Montgomery,” Keith said. “He’s their own…here comes another Brian Cashman masterclass. Go pay top dollar for the kid you drafted, who became a man elsewhere.
“That’s one guy I think is going to be back on the Yankees. Whoever represents Jordan Montgomery, I think is going to make Brian Cashman pay. Brian Cashman feeling the vitriol from fans, the Yankees loving second tours of duty, I would not be surprised if Jordan Montgomery is back on the Yankees.”
Keith could see Montgomery getting a six-year deal near $150 million thanks to his playoff performance, and believes the Yankees would pay it. Meanwhile, he sees them moving on from Montgomery’s former catcher in Kyle Higashioka, clearing the way for a backstop tandem of Jose Trevino and Austin Wells.