I would trade Aaron Judge if you could get a good starting pitcher, a starting outfielder, and a high level prospect in return (not sure he would bring that much). He seems like a great kid and is occasionally spectacular with enormous power but he does not make enough consistent contact, has no clue about situational hitting (like most players these days), is often injured and I don't think his big body is likely to age well plus free agency is coming.
Cashman has made some serious mistakes in the design of this team and this could be a major step in addressing some of the glaring defects.