Instagram
The clarity, when it came, was sudden.
Kyle and Jackie O Show star Jackie O Henderson had spent New Year’s Eve 2025 with her close mates, including activewear entrepreneur Pip Edwards, at a mansion on Sydney Harbour.
The duo posed up a storm in sunglasses – Jackie, then 50, showing off her svelte physique in a white singlet bearing the cheeky caption “Wrong party babe”.
Days later, after feeling “stuck” and turning to ChatGPT for guidance – something Jackie admits “sounds ridiculous” – the star says she had a “revelation”: a defining moment that came to her after years of therapy and reflection.
“I started doing a little bit of work on myself through ChatGPT,” Jackie told her friend and manager Gemma O’Neill in a candid tell-all on the pair’s podcast, Her Best Life, in February, adding that she felt she was repeating patterns in her life at the time.
For “four days straight”, Jackie delved deep into herself with the help of the popular AI agent – asking it for prompts – and said she couldn’t believe the “shift” she went through during that time.
“It was like every piece of the puzzle clicked into place finally. And then suddenly I just felt several things changed for me with that shift.
“My intuition became so loud and clear. It was like I knew instinctively every decision I should make. I knew what I should do with my free time.
“I knew where I should go, where is calling me if I want to go on a holiday. Do I cut ties with a person? Do I change this in my career? Everything was just so clear.
“The love that I suddenly felt for myself shifted as well,” Jackie told her friend.
The star became emotional as she spoke about how turning to writing had helped her overcome a sense of being “unloveable”.
“I have really felt there was a missing piece of me that needed to be filled somehow by something,” Jackie said.
“Whether that was a relationship or something material or maybe it was a certain career or maybe it was validation, but there was this void in there and… there was still that missing piece and now that has been filled by me because I have joy…”
It is perhaps no coincidence that just three short months after discovering this new-found clarity, Jackie O’s path in life has taken a dramatic turn.
On 3 March, ARN Media, the owner of the KIIS FM radio network, released a bombshell statement announcing that Jackie had given notice that she “cannot continue to work” with her co-presenter Kyle Sandilands.
The development came days after an on-air feud between the pair saw Kyle accuse Jackie of being “fixated” with star charts, leaving her in tears.
While Jackie has been offered the possibility of another role at ARN, Celebrity publicist Max Markson doubts the star will return to the airwaves there in any capacity.
“I think Kyle can apologise in the next two weeks and come back and still earn serious money,” the expert told A Current Affair. “He’s got another eight and a half years to go… and he’ll get another partner for his show, which will be a woman. And then, for Jackie, I think she’s walked away from the whole deal.”
It’s not the only thing the star has walked away from.
That candid episode of the Her Best Life podcast was to be Jackie’s last, with the star explaining she wants “to protect a fair bit of my private life now”.
What hasn’t changed, however, is Jackie’s friendships with Pip Edwards and her manager Gemma.
Pip was there to support Jackie as she went public in 2024 with a revelation that she had once battled a drug and alcohol addiction, and is a fierce advocate for the star.
“Jackie O is one of the most humble, interested, invested females I’ve ever met. Who she is and how she speaks, she’s that on the street,” Pip told Stellar at the time
“We’re spiritually aligned, emotionally connected. It’s honest. I think that really shines through in how we interact, even if it’s on Instagram. I just will forever have her back.”
The duo reunited just weeks after their New Year celebrations on February 6, when they were snapped together sunbathing at Bondi Icebergs in photos shared to Pip’s Instagram page.
“Back home and straight into solar charging … but most of all, SOUL charging,” Pip captioned the post.
“Love you angel,” Jackie replied in the comments, to which Pip responded, “Love you more x.”
And while the tearing up of Jackie’s $100 million, 10-year contact with ARN might hurt financially, there are clear signs money wasn’t a factor in Jackie’s decision to start afresh.
The star’s net worth has already been estimated at around $50 million, and she owns a mansion in Clovelly that could hold the key to her future.
The property sits in one of Australia’s most highly-prized suburbs and looks out over the picturesque Gordon’s Bay.
While Jackie raised eyebrows when she snapped it up for $13.25 million in 2023 ($1.25 million above the reserve price at auction), she looks to be laughing three years on.
After a $5 million rebuild, the property – which renders show will boast an expansive pool and gym – will likely be worth a cool $30 million.
While Jackie O’s future path seems secure, what next for the co-star she has so spectacularly fallen out with?
ARN’s statement confirmed Kyle’s behaviour during the 20 February episode of the show was deemed “an act of serious misconduct”.
It was announced that he was suspended and had 14 days to “remedy” the breach or face termination.
Victoria-Jane Otavski, a commercial litigator for Blackbay Lawyers, told Mumbrella the case comes down to the terms of the services agreement in place between the parties.
“Say, for instance, under the terms of the services agreement, it requires both Kyle and Jackie to continue to work together — they need to be an available duo — now that Jackie has made it quite public that she is not coming back, then effectively that breach would be very difficult to remedy … and thereby bring about the termination,” she told the outlet.
“But, whether or not that’s lawful and a step that is available to ARN will turn on the terms of the services agreement.”
In the meantime, neither Kyle or Jackie O have spoken publicly on the matter, although Kyle’s ex-partner Imogen Anthony has weighed in his current woes with a message of support for the shock jock.
“With everyone hoping that Kyle gets cancelled, this man also still helps me look after over 100 rescued animals,” Imogen – who operates the Crimson Peak Animal Sanctuary in the NSW Southern Highlands – wrote on Instagram.
“Kyle often says the wrong thing. I spent 8 years with this man, but I also understand Jackie being an outspoken Aquarian. I also have seen how much he has taken Jackie along every step of the way and ensured that she was treated fairly. I’m upset for both of them to be completely honest and hope they can just snap the f**k out of it.”
