Howard Stern has argued nobody was more keen for Hillary Clinton to win than Donald Trump himself.

The radio personality, who is America’s most notorious shock jock, said President Trump was being serious when he recently admitted to missing his “old life”.

In an interview with Reuters ahead of the 100-day mark of his presidency last week, Mr Trump said: “I loved my previous life. I had so many things going. This is more work than in my previous life. I thought it would be easier.”

Stern, a long-time associate of President Trump, said Mr Trump was “being very honest” when he confessed he missed his former life. Stern explained he had seen exactly what his life as a billionaire property developer and former reality TV star had looked like.

“I’ve seen it up close,” Stern said on his Sirius XM radio show. “[Mr Trump’s] got that kind of life that politicians want.”

“Seventy-year-old guy who has made so much money - he’s made billions of dollars - that he has his own helicopter, he has his own aeroplane. He has a hot wife.”

“He’s got fame from a No. 1 television show. He can walk around Mar-a-Lago, which is like any palace - better than the f*****g White House”.

Over the years Mr Trump was a frequent guest on the Howard Stern Show, appearing on the programme more than two dozen times from the late 90s until the 2000s. And while Stern insists he is not a Trump “insider”, he has referred to him as a “friend”.

Stern recounts being at Mr Trump’s 126-room Mar-a-Lago resort “when he first announced he was going to win” however it is unclear if he is referring to winning the Republican nomination or the November election.

“I was at f*****g Mar-a-Lago laughing about it," Stern said. "I said, ‘What are you, out of your f*****g mind?’”

“Ah, we’ll see what happens,” Mr Trump replied, according to Stern.

Stern argued Mr Trump did not realise how difficult being President would be before he arrived inside the White House, suggesting the President was now dreaming of returning to his old life.

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“What happened to Donald Trump was - and I know about this because I was in therapy for 50 f*****g years, and thousands of hours, and cost a fortune - like Trump, I can’t say no to stuff. I was a workaholic.”

“I didn’t really think about the impact on my personal life. All I would think about is the big announcement,” Stern said explaining how he accepted film and TV contracts.

“[Mr Trump] said, ‘Hey, I can be president of the United States possibly.’ And then when he went out on the campaign trail, and he started to win, it was like, 'Oh my God, I’m going to be president, and all these crowds love me, and it’s going to be fun.' No f*****g idea the shitty life he was going to have."

“He’s sitting in the f*****g White House dreaming about getting to Mar-a-Lago, where he was," Stern continued. “Believe me, nobody wanted Hillary to win more than Donald Trump. He didn’t need this. He’s got the kind of life you dream of”.

Mr Trump’s appearances on Stern’s show frequently came back to bite him throughout his presidential campaign. Topics of women he had sex with and wanted to have sex with frequently came up on the show, with Mr Trump rating women’s appearances. “A person who is very flat-chested is very hard to be a 10,” Mr Trump once told Stern. His lewd and derogatory comments about Lindsay Lohan, including speculating about what sex with her would be like, on the show also resurfaced during the election campaign.