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In 2004, Howard Stern announced he was leaving his longtime home, CBS Radio, for Sirius. The deal reportedly made him the highest paid personality in the business, with stock options he sold for some $200 million. For Stern, the move to satellite wasn’t just about money, it was about creative freedom—he could finally swear on air without incurring the wrath of the FCC. But with satellite radio’s future so closely tied to the tanking automobile industry, the move has not proved to be a successful one. Stern may be laughing all the way to the bank, but his cultural relevance has unquestionably diminished.

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