Only against Cruz or a joke candidate (like Carson, Trump, etc.) could Clinton win KY.
But since the GOP is a joke party, Clinton could win KY anyway.
We'll see. I think Grimes will need a pretty solid victory in the Senate race (5+ points) before I consider it possible that KY could vote for Hillary. If McConnell wins or it's very close, definitely no chance.
It's a young, attractive statewide elected official with Kentucky roots vs. an old career politician dinosaur with a 31% approval rating. If they can't break with their recent GOP trend for that race, they never will.