During a live radio segment where they turned to ChatGPT for therapeutic advice, controversial radio host Kyle Sandilands accused his former co-host Jackie ‘O’ Henderson of labeling him as both a ‘gaslighter’ and a ‘liar’.
The allegations surfaced through documents released by the Federal Court on Thursday as part of Sandilands’ ongoing legal battle with ARN, the company behind KIIS 106.5, following his dismissal from a lucrative $100 million contract.
Sandilands was let go in February after a heated exchange with Henderson on-air, where he criticized her interest in astrology and taunted her for becoming emotional.
ARN asserts that Sandilands’ behavior towards Henderson and other radio staff constituted serious misconduct. However, he argues that ARN pushed for his on-air persona to be ‘dominant and abrasive’, suggesting his actions were justified.
In new court documents, Sandilands contends that ARN not only exploited the fiery dynamic between him and Henderson for profit but also encouraged it, with Henderson reportedly responding in kind.
He cited a specific instance from the November 25, 2024 episode of the Kyle and Jackie O Show, where they engaged ChatGPT in discussions about mental health and relationships.
Kyle Sandilands (left) has taken repeated swipes at Jackie ‘O’ Henderson (right) in his legal defence to ARN’s misconduct claims
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.’
According to the documents, Sandilands points to multiple instances where Henderson mocked, criticised, or insulted colleagues on air
Pictured: Kyle and Jackie ‘O’ Henderson during happier times
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’.
Kyle and Jackie ‘O’ Henderson are pictured at the KIIS studio in Sydney
Sandilands and Henderson are both suing the broadcaster for wrongful termination, while ARN is fighting back, accusing the duo of triggering major financial losses after their ratings‑leading show imploded following the on‑air stoush in February.
According to the court documents, the once rock‑solid friendship – forged over more than 20 years on air –had already fractured months earlier, with a massive behind‑the‑scenes blow‑up in September last year.
ARN alleges Sandilands spoke ‘contemptuously’ to Henderson during an on‑air argument – an incident she has also cited in her statement of claim against the network.
Both stars have launched separate unfair dismissal claims against their former employer, with Sandilands seeking the outstanding amounts left on his and her contracts – $85 million for Sandilands and $82 million for Henderson.
The company flatly rejects Sandilands’ claim that his sacking was unlawful, as well as Henderson’s assertion that she was dismissed for exercising her right to a psychologically safe workplace.
The February on‑air explosion is also alleged to have breached the NSW Work Health and Safety Act.
