Radio shock jock Kyle Sandilands said during a live broadcast that he’d ‘rather be raped in jail than puppeteered by losers’ in a foul-mouthed rant aimed at his bosses and the legal justice system, court documents reveal.

The case files show a KIIS 106.5 boss told co-host Jackie ‘O’ Henderson, through her manager Gemma O’Neill, that the broadcaster had to care for her wellbeing – despite simultaneously saying they weren’t actually required to do so.

Sandilands’ rant was one of about eight listed by radio giant ARN, the owner of KIIS 106.5, in defence documents filed in the Federal Court this week amid Sandilands’ lawsuit over the termination of his $100million contract.

His deal was torn up following an on-air fight with Henderson on February 20 where he slammed her ‘fixation’ on astrology, and then mocked her for crying.

Sandilands argued he maintained a ‘dominant and abrasive personality’ while presenting the Kyle and Jackie O Show because that was what the radio station wanted, and therefore his sacking was invalid.

However, ARN’s defence documents claim Sandilands breached the code of conduct in his agreement to the point where he was banned from criticising staff, talking about legal proceedings against ARN, or mentioning News Corp during live broadcasts.

According to court documents, there was one instance in July where Sandilands berated a censor for dumping a portion of his show, which was done to avoid potentially getting dragged before a court and charged with contempt.

When his manager Bruno Bouchet said during the live broadcast that he didn’t want anyone going to jail, Sandilands replied, ‘I don’t give a s**t, before claiming he’d rather be sexually abused in jail than be muzzled by the law.

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Kyle Sandilands and Jackie ‘O’ Henderson are pictured together

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Kyle Sandilands is pictured with his wife Tegan Kynaston

‘I’m not doing the show anymore as of this second. So good luck,’ he said.

‘Here’s the ads. Enjoy the ads. Maybe I’ll be on an ad. Maybe I won’t.

‘That’s the show ripped up. Judges can shove it in their a**. ACMA [Australian Communications and Media Authority] can shove it in their a**.

‘So can the management of the radio station.

‘Two hands straight in the anus. And clap.

‘That’s a loose a**. Enjoy the rest of the week guys. Arrivederci from me.’

Sandilands then left the studio.

In another rant on April 30, Sandilands made a series of disparaging comments about Melbourne listeners, and ARN’s attempt to improve dismal ratings in the city.

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Jackie ‘O’ Henderson (pictured) is suing her former station KIIS 106.5

‘Here’s something I haven’t even discussed with Jackie. If we don’t rate better by the end of this year, I’m pulling the carpet out.

‘I’ll just take the show off Melbourne. You can suck my d**k.

‘We’re not just going to suck Melbourne off all day, every day.’

Other charming rants included further attacks on the government and contempt laws, while continually firing off blistering attacks on his colleagues, calling them ‘p*ssies’ and ‘flops’, and threatening to leave ARN.

Henderson also lost her $100million deal. She is suing ARN over claims it breached the Fair Work Act by failing to ensure she was provided with a safe workspace, and then terminating her contract when she insisted on one.

In response to Henderson’s matter, ARN said it didn’t breach the Fair Work Act because she worked for her own company, Henderson Media, which was instead responsible for ensuring the star’s health and safety while doing the show at ARN.

Henderson and Sandilands signed their contracts using their respective businesses, Henderson Media and Quasar. ARN says they were therefore employed as contractors from those businesses, rather than as individuals under direct employ.

However, the broadcaster’s defence material in Sandilands’ matter does include a lengthy email from former radio boss Lauren Joyce to Henderson’s manager, saying ARN did have Fair Work Act obligations.

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Jackie ‘O’ Henderson is pictured with her manager and best friend, Gemma O’Neill

The email was sent on September 16, after Henderson had made complaints about Sandilands’ behaviour to her ARN bosses, and five months before their relationship fell apart.

It read: ‘Dear Gemma – following our call yesterday, I want to acknowledge the seriousness of what you shared regarding the argument between Kyle and Jackie and Jackie’s feelings of being bullied.

‘I want to be clear – this is a serious matter, and Jackie’s wellbeing is our priority.

‘As you know, ARN has obligations under the Fair Work Act to ensure a safe workplace, including protecting people from risks to their psychological health.

‘We are absolutely committed to upholding those obligations and to making sure Jackie feels safe, supported, and respected.’

She then asked for Henderson’s account of events to ensure the matter was properly dealt with.

The co-hosts relationship finally imploded on February 20, when Sandilands said Henderson’s ‘fixation’ on astrology made her ‘almost unworkable’ – to the point where she left the studio in tears.

Sandilands then said: ‘You can’t start crying about it, it’s not that big a deal.’

On February 26, Henderson’s lawyers wrote a letter of complaint to ARN explaining the broadcaster had been notified about Sandilands’ ‘bullying’.

The letter said Henderson ‘could not continue to work with Mr Sandilands’, but that she was willing to continue her contract with a different show.

In the days that followed ARN terminated both their contracts.

Henderson and Sandilands’ matters will be mentioned in the Federal Court on Friday.