Kyle and Jackie Os Tension Exposed by ChatGPT

Radio shock jock  accused his former co-host of calling him a 'gaslighter' and a 'liar' during a live segment where they used as a therapist.

Sandilands' claims were revealed in a tranche of documents released by the Federal Court on Thursday amid his civil case against ARN, which owns KIIS 106.5, over the termination of his $100 million contract.

He was fired in February following an on‑air argument with his co‑host, when he slammed her 'fixation' on astrology and then mocked her for crying.

ARN claims Sandilands engaged in serious misconduct in his treatment of Henderson and radio staff, but he claims ARN wanted him to which he says meant his conduct was reasonable.

According to fresh court filings, Sandilands has now claimed ARN not only exploited his and Henderson's fiery relationship for financial gain, but also encouraged it, and that Henderson routinely matched his tone.

His primary example was during a broadcast of the Kyle and Jackie O Show on November 25, 2024, when they were asking ChatGPT questions about mental health and relationships.

Henderson asked: 'This is bulls**t. Don't listen to [Sandilands]. He's a liar, that's my truth. How do I tell my colleague all he does is exaggerate and lie? He's a gaslighter. Is my truth not important?'

That segment was replayed on KIIS 106.5 three times last year, on February 12, June 12, and November 25, which Sandilands claims was evidence of KIIS monetising their behaviour.

Sandilands posed his own questions during the AI therapy session, asking: 'How should I deal with a colleague's constant mood swings?'

He also asked: 'How should I stop making drug-related jokes around my colleague who's currently a recovering addict?' and 'How do I tell my work colleague I think she's dating way too many different fellas?'.

Henderson previously opened up about her three-year addiction to painkillers, sleeping pills and alcohol.

That portion of the segment was also replayed three times. 

Another example was on November 29, 2023, when Sandilands called in sick the day after they had an off-air argument.

According to the court documents, Henderson asked her radio bosses why they didn't include the fight in the live broadcast because it could have attracted their 'highest ratings'.

She said: 'Why didn't we put it? Oh, well, what are you going to do, put a podcast? Which is the fight, people would tune in for that.'

She also said: 'They would actually probably get our highest ratings. No, we had a fight. It was so stupid. People said to me, what was it over? And I was like, I don't know.'

The argument was included in a podcast that day, titled, 'The REAL reason Kyle left the show yesterday', with the description: 'Yesterday's show ended quite abruptly when Kyle left. 

'It all seemed quite heated but Jackie has cleared the air with what really happened. Have a listen for all the details.'

Sandilands further claims Henderson questioned the legitimacy of his sick days on air and made disparaging remarks about him when he was absent – reinforcing his position the commentary was part of the show's accepted dynamic.

In an off-air argument in February last year, Sandilands complained about Henderson's performance at work, saying, 'You were away with the fairies.'

He continued: 'There's no accusations. You were, we were laughing because you were off with the fairies and you weren't paying attention. And everyone spoke to you six times.'

According to Sandilands, Henderson replied and said she was 'constantly getting f***ing gas lit around here'.

Sandilands replied: 'Don't go pulling up those f***ing lying statements. We can't mention anything to you ever. Gas lit. Can you believe it?'

The off-air argument was played during a couples counselling segment on May 5, 2025, and included in a podcast titled, 'Kyle & Jackie's unheard EXPLOSIVE off air fight'.