The future of Howard Stern’s long-running SiriusXM radio show is in jeopardy as the end of his $500million five-year contract looms.

Radio personality Stern, 71, has been hosting The Howard Stern Show since 2006, and a show insider told the Daily Mail that he is in ‘very serious negotiations’ with SiriusXM regarding the renewal of his contract.

Stern’s transformation from having a notorious reputation in American entertainment to being labeled by Kanye West as an ‘irrelevant old man’ has been stark in recent years. He has faced criticism for proudly admitting that he is ‘woke’.

The insider explained, ‘He might consider a 1-2 year contract if his financial terms are met. He doesn’t want to leave his team in a difficult position.’

Another source revealed that Stern is contemplating ‘parting ways’ with SiriusXM, and his team of ‘around 95’ writers and producers only recently learned of Stern’s uncertainty about the show’s future.

They added the star ‘will likely sell his catalogue of shows to replay’ on uncensored channels Howard 100 and Howard 101. 

The future of Howard Stern’s 20-year SiriusXM radio show is in jeopardy as the end of his $500million five-year contract looms – pictured April 2024

Radio personality Stern, 71, has hosted the second version of The Howard Stern Show since 2006, and an insider confirmed to the Daily Mail that he is in ‘very serious negotiations’ with SiriusXM on his contract renewal. He is seen with Madonna in 2015.

‘He is off in the summer but this year has been saying “maybe I should retire”‘, the source said.

It is possible Stern could also return for specials with SiriusXM.

The source claimed Stern was also displeased over SiriusXM ‘leaning heavily’ on fellow radio star Andy Cohen. 

Daily Mail has contacted representatives for Howard Stern, SiriusXM and Andy Cohen for comment and has yet to hear back. 

In 2023, after hearing criticisms that he’s ‘not good anymore’, Stern responded, ‘I take that as a compliment. Being woke is important to me. The opposite of being woke is being asleep.’

‘And if woke means I can’t get behind Trump, which is what I think it means, or that I support people who want to be transgender or I’m for the vaccine, dude call me woke as you f*****g want.’

The radio star’s career fell from having 20 million listeners a day to to figures fans believe are as low as 125,000. He has predominately broadcast from his home over the past five years, citing fears over COVID-19.

Dubbed the ‘King of all Media’ – Stern first launched The Howard Stern Show in 1986 on terrestrial radio. 

Stern’s shift from having the most fearsome reputation in American entertainment to being what Kanye West described as an ‘irrelevant old man’ has been dramatic and he has faced backlash after admitting he was ‘woke’ in a dramatic 2023 interview – pictured with Seinfeld in 2013 

Donald Trump appeared on Stern’s show 20 times before becoming president, appearing with daughter Ivanka at one time

Khloe Kardashian has appeared on Stern’s show, once with her sister Kim, where she confessed she only dates black men 

Stern is pictured at the height of his influence in 1995 in NYC alongside longtime cohost Robin Quivers

The source claimed Stern was also displeased over SiriusXM ‘leaning heavily’ on fellow radio star Andy Cohen. – pictured last month 

Stern decided to take on the challenge of pulling together interviews over the years where he was able to draw out shocking confessions.

President Donald Trump has been on the show more than 20 times – calling in or being in the studio because he was willing to say anything.

In 1997, he admitted to seeing a lot of women and when asked if he wore a rubber he said he hoped for the best.

He also branded daughter Ivanka ‘very voluptuous’ in an 2006 interview.

In 2019 book Howard Stern Comes Again the DJ confessed that his biggest regret is that he never got to apologize to Robin Williams after his interview in the early nineties.

‘When Robin came on the show, I spent the entire time badgering him about how he had divorced his first wife and remarried his son’s former nanny. I was attacking the guy, and he was justifiably furious with me’, Stern writes.

Stern only realized years later that he needed to apologize – after years of psychotherapy to understand his own narcissism that had prevented him from even considering what someone else might be feeling.

Twenty years after the interview, he got up the nerve but it was too late. Robin died before Stern could make that call.

‘I’m still filled with sadness over his loss and remorse for my failure to reach out sooner’, he admitted. 

Kim and Khloe Kardashian came on Stern’s show in 2009 and he admitted, ‘I didn’t understand their talent. I didn’t even know if they had one.’

So he asked Khloe about dating black men.

‘Once you go black, you just never go back,’ she said, admitting to only have dated black men.

But Kim said Khloe’s rule isn’t’ always true. ‘She’s only black guys, I’m not’.

‘Maybe it’s because we have such big a**es, like the black guys like,’ Kim said.

Both admitted to liking to be spanked, getting their hair pulled and talking dirty in bed.

Stern has hosted and produced late night television shows, pay-per-view events and home videos, and wrote three books, two of which sold over one million copies.

He has become controversial for some comments he made over the years, including saying some of the girls running from the Columbine High School shooting were ‘really good looking girls’ – Columbine shooters Eric Harris and Dylan Klebold pictured

In March 1995, when Selena’s fans reeled from her shooting he made fun of them, playing gunshots over Selena’s music the day before her funeral and mocking Selena’s fans with a fake Hispanic accent – Selena pictured 1994

He has ignited fierce criticism over his several outrageous remarks, including saying some of the girls running from the Columbine High School shooting were ‘really good looking girls.’

‘Did those kids try to have sex with any of those good-looking girls?’ he asked on his show, about the shooters. ‘They didn’t even do that? At least if you’re going to kill yourself and kill the kids, why wouldn’t you have some sex? If I was going to kill some people, I’d take them out with sex.’

In 1992 he also mused that the ‘closest I came to making love to a black woman’ was when ‘I masturbated to a picture of Aunt Jemima on a pancake box,’.

In March 1995, when Selena’s fans reeled from her shooting he made fun of them, playing gunshots over Selena’s music the day before her funeral and mocking Selena’s fans with a fake Hispanic accent.