Interesting WSJ article about Howard Stern and his upcoming contract renegotiation. Basically he can either re-sign with Sirius satellite radio or go back to terrestrial radio. The article floats the idea of some kind of internet streaming but I don't think the technology is there yet--most people listen to Howard in their cars, not on their desktops.
My guess is he re-signs with Sirius but for less than five years (the better to see where technology goes) and less than $100 million per year. Sirius has more leverage than it did four years ago now that it doesn't have to worry about another satellite competitor, but it doesn't have THAT much leverage. Terrestrial radio still has enough money to pay Rush Limbaugh $400 million over eight years. The other thing is that, as a super high-fixed cost business, Sirius can ill afford to give up significant subscribers.