Howard Stern apparently announced that he was retiring only to take it back immediately. According to Loudwire, Stern took the airwaves to announce that he has not plans to retire and the discuss between him and Robin Quivers about quitting at the end of his contract was a joke.
Stern said that he has not made a decision on his future past his 2020 contract expiration. Should Stern decide to retire, I don’t think that they would be any questions on his future.
Stern’s looming retirement (be it in a year or after his next contract expires) would open a ton of money for SiruisXM and open up market space for new talk radio show.