Biggest reason Wes won't ever be a Cav is their ugly uniform. Just wouldn't be a good look for Wes. I think Wes also enjoys being more of an alpha dog in Portland instead of having those egos around him.
if the cavs still had wiggins id do it but no one on their roster fits here (That they would move for Wes anyways. LBJ/Love/Kyrie aren't moving for wes lol)
But let's be honest, I don't believe Wes would choose James over his teammates here in Portland. He's in a pretty good situation. As long as we continue to want him, I think it will continue to be a happy marriage.