Howard Stern is up to his neck in promoting the freaks and outcasts of society. That’s where he got his ratings.
Perhaps many of these freaks are actually transgenders. It may have been implied, but it was never mentioned directly.
Howard himself may be “married” to a transgender. This may be a ruse, and he may really still be married to his first wife. We have no way of really knowing.
I do believe he is out promoting a perverse agenda, while living a normal life.