With the new trend of more and more radio stars moving towards the internet and podcasting, I could see a future where if Sirius goes out of business, he could continue broadcasting online, possibly for pay or for free.
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Personally, I doubt he would right away, taking a watch and wait approach. But if Sirius XM defaults on this contract (depending on all of the many details and clauses that are part of his contract) and he sees some serious warning signs, he may just take whatever money he has socked away and retire from radio.

That's just my opinion. Nothing concrete, but based on various conversations he's talked about on the air about retiring from radio and resigning his contract.
Source(s):
Howard Stern's various discussions and thoughts about contract resigning and retiring from radio.

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As Stern has a contact, he will see that out, but after that (2011) Sirius XM probally won't be able to afford to renew him.
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One of the main advantages to a struggling company of declaring bankruptcy is that it gets to cancel or renegotiate contracts. Analysts seem to agree that Howard Stern's contract is a huge burden on the company. On the other hand, it can't afford to lose subscribers. If they do go bankrupt they will undoubtedly try to negotiate a less expensive contract. Howard Stern will probably use the opportunity to switch to another network if another network makes a decent offer, since he would neither want a pay cut nor want to work for a company that might go out of business at any time.

He will only go off the air, as you ask in your question, if he loses his popularity. Otherwise it's just a matter of who is his employer.
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SXM probably won't be able to pay him enough, and he might move back to terrestrial radio, or possibly Internet radio or podcasting.
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As of February, Sirius XM is not going to be going bankrupt for at least 2 years, so the question is mute.

Oboewan is incorrect: Stern said on his show this week that he wanted to stay on Satellite Radio, but perhaps with an extra day off. (He currently only works 4 days per week, with Fridays being reruns).

Will will probably renegotiate his contract with Sirius to include an extra day off, and he will get a smaller paycheck. I think Stern stays on SatRad until at least 2015
Source(s):
http://www.satwaves.com


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