He'll declare that radio is dead when his contract expires. A Larry King type TV gig follows before eventually replacing his pal Letterman.
Howard would love to get a prime time talk show but I don't think TV executives would ever take him seriously. I don't think he's that good of an interviewer. He likes to play amateur psychologist too much. Howard thinks he's a psychology expert based on his years of therapy. His show has turned into an audition for a talk show with Howard supposedly demonstrating his "awesome" interview skills, which amount to him being a kiss up flatterer and saying "uh huh uh huh uh huh" after everything the D list guest says. And with his new dentures/veneers, he sounds like Sylvester the Cat most of the time.
I think he's shit all over his legacy. He'll go out with a whimper...and maybe in 5-10 years people will be able to forget the huge shit fest the HSS became during the 'revolution'. Only then will people be able to remember the laughter.