Sirius stock is just a buck, Howard Stern's contract is up for renewal, and his investment is not paying off. So what is the self proclaimed "Master of all Media" supposed to do when his listening audience is miniscule. Perhaps get back to free radio.
While Howard's humor is not appreciated by all, what makes him funnier is pushing the line, not crossing it. When he is forced to stay on one side of the line of decency, his humor becomes more biting, more targeted, more creative. With too much freedom comes the low brow humor, the easy joke, the gross simply to be gross. Rules were Howard's enemy but they also gave him something to talk about and a tension that can make for truly funny.
Will Howard resign with Sirius or go back to terrestrial radio? While it is hard to read a lot into his current comments, it is clear to me that it is time to take the risk again and get back to basics. Over the air radio misses Howard and I believe Howard misses the larger audiences also.