"Making a play" for New York isn't about winning New York. It's about projecting a certain kind of strength to suburban voters elsewhere, like in the Rust Belt.
"Gee, if Trump thinks he has a shot at winning moderate/liberal New York, he must not be so bad!"
And it won't upset his hard right Southern voters either because they'll be impressed that he's such a #winner and going for broke.
Delusional nonsense. Trump could wander out on stage, soil himself, mutter like a demented Brando for an hour and then stumble off and his cult would start explaining his secret genius.
Oh, wait. That's already how it works.