‘The stigma that will come with sharing this – I don’t care’: Jackie O opens up

This story is part of the Good Weekend: Best of Features 2024 editon.See all 12 stories.

Jackie Henderson struggles to pinpoint her first slip on the slide into addiction, but it was probably seven years ago. Back when her marriage was breaking down. When a glass of white wine wasn’t quite enough relief from the sadness or stress of the day, and a few Nurofen Plus seemed an easy added release or retreat. The specifics blur.

Yet the Sydney broadcaster clearly recalls where her nadir unfolded. She was divorced and living in a new home in the exclusive eastern enclave of Woollahra. The palatial house had seemed a haven when the co-host of Australia’s most provocative and polarising radio program – the Kyle & Jackie O show – bought it in 2020.

But during pandemic lockdowns, particularly at night, the gleaming modern build came to feel more mausoleum than mansion. “It was hell, because of how quickly I spiralled in that house,” she says now, sitting on a soft leather couch in the sun. “I went deep into my addiction there. It’s a beautiful house, but it felt like a fortress. My concrete prison.”

It was there that her painkiller use – then just a few over-the-counter pills to take the edge off – increased, at her worst, to a daily boxful of prescription Panadeine Forte. As many as 24 potent codeine tablets, swallowed six at a time, washed down with a gin and tonic.

It was also there, on the days she didn’t have custody of her daughter Kitty, now 13, that her loneliness inspired another bad call – by adding up to an entire box of 14 powerful Stilnox sleeping pills to her daily intake, sinking her into a sad yet smiling oblivion.

Henderson, now 49, became a hermit, recording her radio show remotely each morning from a makeshift studio upstairs, before returning to her chemical comforts. When friends began noticing her blackout forgetfulness – “Jackie, we talked about that last night, remember?” – she covered her tracks by scrawling real-time Post-it Note reminders of phone conversations.

“There’s been so many times where I’ve wondered, ‘Should I just say it?’” says Henderson of choosing when to talk on air about her drug habit.Credit: Tim Bauer

Her manager, Gemma O’Neill, noticed these behavioural quirks but rationalised them on behalf of her star client. Jackie seemed a little drunk today. OK, but have you been through a divorce lately? She’s sleeping an awful lot, too. Sure, but do you get up at 4am every day for a breakfast radio shift? She’s bordering on reclusive now. Didn’t COVID-19 do that to us all?

O’Neill tried to pull her formerly bubbly bestie out of her social cocoon, suggesting a walk or a swim or a meal, but was almost always rebuffed. “I thought for a while there that she’d developed agoraphobia,” O’Neill says. “Honestly, that’s what I was leaning into, because the reality was so far from what I would ever have guessed.”

Personal assistant Brittany Woodford fought to ignore the empty blister packs of unfamiliar medication she came across in her daily duties, professional respect for privacy trumping personal inquiry. “It was so hard to sit in that – to see someone you love suffering,” says 35-year-old Woodford, who does everything from balancing Henderson’s hectic diary to getting Sadie the cavoodle groomed. “There’s a line though: she’s like my sister, but also my boss.”

Eventually Woodford began leaving gentle, plaintive letters for her employer to find: “I don’t know what to do, and I know I can’t overstep the mark, but you need help.”

Henderson’s mother, Julie Last, had no luck breaking through, either. She had no idea her daughter was addicted to medication, and was more concerned by the binge-drinking she saw when visiting from her home on the Gold Coast. Her happy, empathetic girl seemed to turn so stormy whenever her lifestyle was raised. “She would shut you off: ‘Mum! Let’s just have a good time while you’re here,’ ” says Last, 78. “Every time I would bring it up, she would bite my head off. It just wasn’t her.”

With her mum, Julie Last, who didn’t know about the pills – but was worried about her daughter’s binge-drinking.Credit: Courtesy of Jackie Henderson

Earlier this year, I helped Henderson write her biography – The Whole Truth, to be released on Tuesday by Penguin Random House – and over multiple interviews, she explained to me how diminished, untethered and alone she felt in her new life. “By that point I had no self-esteem, so I was insecure, vulnerable and heartbroken,” she told me. “It was a recipe for disaster, and I took the coward’s way out to escape those feelings.”

How does it feel to look back on the person she was at that time, before she entered rehab at the Betty Ford Centre in Rancho Mirage, California, in late 2022. Does she even recognise herself? “I feel mostly sad for that girl,” she says now, pausing. “I wish I could shake her and say, ‘If you could just go get help, everything would be so much better.’ I’m sad that she couldn’t see any light, that she thought her miserable existence was an acceptable one – to be living a life that’s not a life at all.”

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When we talk again this month, Henderson looks well, having just returned from a holiday in New York, a wedding in Las Vegas and a week of broadcasting from Los Angeles. She’s on the couch at home, in the clifftop Clovelly rental where she’s waiting for her knockdown-rebuild dream house to take shape around the corner (she sold the Woollahra home in 2022 for $13 million).

This is where I first met her, on an overcast day back in autumn. She sat there in an Anine Bing sweatshirt, tortoiseshell Prada sunnies hiding her eyes, knees hugged into her chest as if bracing for something. The Jackie O Post-it Note version of our conversations about her life? Let’s save time and hit the bullet points …

Carefree misadventures in a sun-bleached Surfers Paradise childhood. Catholic school and TAFE typing classes. Reception jobs and clubbing on Cavill Avenue. A first marriage (and later divorce) to DJ “Ugly Phil” O’Neil. Her start in radio thanks to him – minor roles growing in Canberra, then Adelaide, then Melbourne, then Sydney. An unlikely new partnership with a brash blond bogan – a broadcasting unknown from Brissie. Gaffes and laughs, headlines and notoriety, fame and fortune, with the one and only Kyle Sandilands. Love and a joyous IVF journey – in a second marriage (to former photographer Lee Henderson), then second divorce. Hilarious and heartbreaking adventures in the world of 40-something singledom. Last year’s record 10-year $100 million contract, and this year’s ill-fated foray into the Melbourne media market.

That gets us neatly up to date on everything except the moment that forced her into rehab, and the rebuilding of a healthy new life. Henderson shared part of that story with her KIIS FM listeners this week but has been otherwise silent on the matter for two years.

‘I didn’t want to get out of it. In a sick, twisted way, I thought I was happy where I was.’

“There’s been so many times where I’ve wondered, ‘Should I just say it?’,” she says. “But then I’d think, ‘I have the right to keep this private until I’m ready, because sobriety is a really fragile thing.’ ”

As she explained two days ago on air, her life changed on Sunday November 6, 2022, the day her supplier called to say they’d been busted and could no longer feed Henderson’s habit for prescription medications. Her first panicked phone call that afternoon – hyperventilating through sobs – was to her manager, Gemma O’Neill. “Once Jackie revealed everything to me,” says O’Neill, a veteran broadcast executive, “in my head there was no other option but rehab.”

With manager Gemma O’Neill, who wasn’t keen on the idea of a memoir.Credit: Courtesy of Jackie Henderson

Henderson initially thought otherwise, arguing that she could use the two-week supply stashed in her safe to taper off the drugs safely. “I was never coming out of it on my own. No way. Because I didn’t want to get out of it,” Henderson notes. “In a sick, twisted way, I thought I was happy where I was.”

O’Neill stepped up, establishing an unfamiliar parent-child dynamic with her old friend. “She really was like a child – screaming out for help but pushing you away,” O’Neill says. “But there was also part of her that was giving in. I think she was exhausted.”

O’Neill booked a place in the famed Betty Ford rehabilitation clinic, out of the public eye, hoping to avoid the potential circus of seeking treatment in Australia. “But I couldn’t really plan that out with Jackie, because she wasn’t in a coherent state.” They pre-recorded a message for listeners, saying Henderson needed rest after a bad bout of COVID (which was also true), knowing from experience that paparazzi would stake out her house after the announcement.

The full cloak-and-dagger operation was complete when they flew to the US undetected, Henderson disguised in baggy clothes, hat and face mask.

And rehab itself? The Coachella Valley clinic conjures Tinseltown grit and glamour – the institution where Robert Downey jnr and Drew Barrymore were treated – but it’s no longer where the stars go for recovery. It felt to Henderson more like a cross between a doctor’s office and a two-star hotel, a temporary home to everyone from young rural fentanyl users to a Formula 1 engineer with a drinking problem to a 58-year-old lawyer addicted to crack cocaine. She became deep and abiding friends with them all during her month-long stay – and took stock of her life.

After the physical tumult of detox – nausea and insomnia, sweating and diarrhoea – she embraced the 12-step program of lessons and gatherings and exercises from 6am to 8pm, every day for 28 days. She came to an uncomfortable epiphany about her functional but fraught relationship with alcohol, including the realisation that she’d not gone a single day without a drink since having Kitty more than a decade prior.

“I’d actually been adamant that I was going to come out of rehab and still drink. I didn’t want to be sober my whole life – that thought was quite depressing,” Henderson says. “But coming to the understanding that I was dependent on alcohol was eye-opening for me.”

She still misses it sometimes, like those buzzy moments on holiday when the champagne comes out to start the night – pop, clink, fizz – but recognises it’s not for her. Not any more.

“I would have leaned on that, using alcohol as my form of escape instead of pills,” she says. “I just knew that it had to be all or nothing for me.”

It was only near the end of treatment – after so much reading and journalling – that she decided to write a book. The prompt came from her counsellor. “She said, ‘Did you ever think maybe this was the reason you were given your platform?’ and the penny dropped. Something clicked, and I just knew I was going to be telling this story.”

With assistant Brittany Woodford, who says she’s like a sister – and her boss.Credit: Courtesy of Jackie Henderson

Still, it needed to be done in her own time, meaning the truth had to be quarantined to a tightly guarded handful: Henderson’s parents, her ex-husband Lee (Kitty’s father), O’Neill and Woodford (the assistant).

Until this week, Henderson’s best friends, her bosses at KIIS FM, even Sandilands – who she’s described as the most important man in her life – were all in the dark. “I know Kyle,” explains Henderson of keeping it from him. “If I told him something in confidence, he’s never going to outright say it on air. But he might have a tiny little slip, and I just didn’t want anyone to know.”

The protective O’Neill didn’t like the idea of a memoir. “Why would you?” she reasoned. “No one knows. And she’s better now. Why would you risk the media scrutiny and the judgment and all of it?”

Direct questions like “Why the big break from radio?” were easy enough to parry. She was unwell when she left. She did need time to address her health. “All of that is true,” Henderson says, “so I kept sticking to that story because I felt I wasn’t lying.”

Timing helped. Henderson only missed three weeks on air because the show was due for its six-week summer break, minimising tabloid curiosity. Her dramatic weight loss was explained by new healthy eating habits, swimming at Clovelly, cycling on a high-tech Peloton exercise bike and playing tennis. (When she couldn’t find a hitting partner, she invested in a ball machine.) Others just assumed she was taking Ozempic. (She says she wasn’t.)

Her team at KIIS FM tried to guess the reason for her sabbatical, keeping a running list of wild theories. Jackie was having gastric bypass surgery. Jackie was having cosmetic surgery. Jackie was having vaginal rejuvenation surgery. She was having a baby. Or creating a new reality show. Or an OnlyFans account.

Sandilands came closest to the truth, addressing Henderson’s mysterious time away by joking with listeners that she had probably been at the Betty Ford Centre. “I just had to laugh it off or change the subject without looking too obvious,” Henderson says. “But there were moments of panic. I’d hate for him to have turned around to me and go, ‘Did you go to rehab? ’”

“I would have leaned on that, using alcohol as my form of escape instead of pills ... I just knew that it had to be all or nothing for me.” Credit: Tim Bauer

With her co-host making light of addiction, I wonder what this whole experience has taught Henderson about their infamously “unfiltered” style of radio. They used to do an intervention segment on the show – confronting a co-worker about their bad breath, for instance. It seemed harmless enough until one day, about 15 years ago, a schoolteacher called out on air the alcoholism of a 40-something colleague. The moment passed without public mention, but Henderson recognised it as horrible.

“But something strange happens when you’re on air,” she writes. “Half of your brain is thinking like a normal human being – ‘This is f---ed up’ – but the other half is in entertainment mode – ‘We’re delivering something for the audience to talk about today’ – meaning you end up with this distorted and split perspective.”

She discussed that exact episode in rehab, in fact, because she remains “deeply ashamed” of it. Of other moments, too. Henderson remembers calling to apologise to Magda Szubanski after Sandilands made a joke about the Jewish-Australian comedian’s waistline: “You put her in a concentration camp and you watch the weight fall.”

Szubanski took the call and was gracious. She said she understood Henderson hadn’t done anything personally, but she also shared a clear message: “If you lie with dogs, you’ll get fleas.”

And so we come to the braying, barking bloke Henderson sits alongside every weekday. The litany of complaints against “Vile Kyle” would take too long to list, but two recent zingers to breach Australian Communications and Media Authority decency standards were referring to the Paralympics as “horrific” and describing the monkeypox virus as “the big gay disease”.

‘I have to remind myself that it’s not my job to control what (Kyle Sandilands) says.’

If you’re waiting for her to criticise him, though, you’ll be waiting a while. That said, Henderson’s view on Sandilands’ antics is nuanced. When he’s at his absolute sharpest, she feels on edge – likening it to being at a party with your husband, and he’s drunk and holding court, and everyone is laughing along and you smile, too, but you’re wincing inside. “I have grappled with that over the years,” she says. “But the more I learn about boundaries in my life, and understand myself better, I have to remind myself that that isn’t me, that we are two separate people. I’m not saying what he’s saying.”

Sitting on this fence seems to have earned Henderson particular ire. To some it’s almost as though she’s more deserving of judgment than her counterpart: she should know better, she’s a woman. “If I feel uncomfortable with something he says, I can say so – and I do feel better doing that these days – but it is hard,” she admits. “I feel the weight of any comment he makes, because, you know, we are ‘Kyle and Jackie O’ – it’s like we’re one and the same – so it’s hard not to feel somewhat responsible. But I have to remind myself that it’s not my job to control what he says just because I’m the female in the situation.”

Henderson likens broadcasting with Kyle Sandilands at times to wincing at a drunk husband holding court at a party.

What about aligning yourself with someone so wholeheartedly, thereby aiding and abetting their puerile shtick? She’s heard this kind of “accomplice” label before, too. “If you had decent morals, you wouldn’t be on the show in the first place,” she says, paraphrasing the charge. “And I can understand that perspective, but I would only ask that you judge me on the things I say, not the things somebody else says.”

What about when Sandilands wants her to play in his specifically sexual sandpit? When he draws Henderson into chatter about her experience with anal sex, for example, or talks to a stripper about giving blowjobs to men wearing condoms and offers this little concluding witticism: “Jackie goes bareback, all the way.”

“Here’s the thing,” she explains. “I’m not overly sensitive to this stuff, and sometimes I’ll just let it go because it’s not worth going ‘I don’t do that!’ Or maybe I’ve been desensitised to it over the years. If I have a problem, I say something, but you pick your battles and sometimes I just let it slide.”

How the public reacts to her recent struggles will prove an interesting case study. O’Neill believes fans will be shocked but empathetic. And the haters? “It’s the great unknown,” O’Neill says. “They’re either going to continue to hate, and use Jackie’s news as a reason to hate even more, or they’re going to see that she’s a human being.”

To Henderson’s mind, speaking out is about helping people; letting them know they aren’t alone, motivating them to seek help and change their life. “And the downside – the negative opinions and the stigma that will come with sharing this – I honestly don’t care,” she says. “If you’re a hater and this makes your opinion of me lower, I’m OK with that. I really am.”

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Of course, it feels right now as if many of the aforementioned haters are confined within one progressive geographic patch – the spot roughly 800 kilometres south-west of Sydney called “Melbourne”.

Launched with great fanfare into the highly competitive Victorian breakfast radio market earlier this year, the Kyle & Jackie O show limped along for a few ratings surveys before slumping to eighth place with a lowly 5.2 per cent share earlier this month (in Sydney, they’re No. 1 in breakfast with a 13.7 per cent share). Day one of the newly syndicated show, beamed south from their harbour-view studio, included talk of extra long foreskin and vaping from a vagina, and a random interjection from self-professed “ex-F-boy, coke-sniffing arsehole” Sandilands: “I don’t suck dick, nice to meet you Melbourne.”

Henderson laughs as she recalls the “wild” first few weeks. “I don’t know what Kyle was doing, but I think he thought he had to be even more smutty. Anyone who listened to the show the first week would have been thinking, ‘Oh my god, this is bordering on pornography’ and they would have been right, but it was not quite where our show usually sits.”

Indeed, The Age’s Stephen Brook listened to the entire first week of the show and found it “weirdly compelling” – but he also couldn’t sugarcoat the latest result: “Like an alien spaceship from Planet Porno, the arrival of Sydney breakfast shock jocks Kyle and Jackie O on Melbourne radio this year was an attempt to crash through ingrained media parochialism,” Brook wrote. “Instead, they’ve just crashed.”

Henderson gets it, but is hopeful about the other little indicators she sees, like Victorian callers starting to slip into their switchboard stream. Having worked in this market before (at Fox FM, albeit a quarter of a century ago), she says she always knew they would “weather a big storm” upon arrival. “Once it calms down, it will slowly increase,” she predicts. “In my view – it will take maybe two to three years to get there. It’ll happen slowly.”

In the meantime, she’s looking forward to being an open book – literally. She writes of many experiences from the weird world of broadcasting in her memoir, from joyful moments with the delightful Ed Sheeran to seeing sadness in Justin Bieber’s eyes. There was the charismatic and “utterly terrifying” radio executive who had a samurai sword in his office and would chop the edge of his desk every time he fired someone. And there was the tour promoter who didn’t realise Henderson was married to Ugly Phil and called her to ask if he would like cocaine supplied for an upcoming trip, and what kind of hookers he preferred.

Henderson is single now, but not for lack of trying. With her health intact and vitality restored, she re-entered the dating world last year, unashamedly looking for love. There was the landscaper from Cronulla and the architect from the northern beaches. There was the ex-athlete and the actor. There was the guy who spat in her mouth without warning during sex, and the one who cooked dinner for her while naked, thinking his bare arse in an apron would be a sexy surprise.

Now 49, Henderson seems happy to revel in just how bizarre blokes can be, particularly for post-divorce women entering the digital dating arena in their 40s. “I thought it was important to show what it’s like – and what a shock it is. ‘Who’s out there? Is it full of nightmare men? Is it as brutal as what you hear?’ ”

Having been married on and off since she was 19, Henderson used to pine for that one wild year of singledom she missed out on during her prime. Not any more. “For anyone who’s experiencing those thoughts or desires, I wanted to let them know: it’s not all it’s cracked up to be!”

For her it included heartbreak after a more serious three-month relationship broke down earlier this year. Her mum helped her through that one. Their daily calls had subsided during Henderson’s addiction but revved up again during the breakup, the pair talking daily, often for three hours at a time. “I’d say, ‘Maybe I should go now?’ ” Last says, “and Jackie would go, ‘No, Mum, just stay. Even if we don’t talk, just stay.’ ”

It would be easy to peg Henderson as a simple socialite with the azure eyes and latte tan, and that tendency to call everyone “darling” and “honey”. But she’s affectionate and unfailingly attentive, wanting to know where you’ve been, how you’re going and where you’re headed – if you’ve eaten enough of the shared sushi meal, if the wind is too cold for sitting outside.

Her idea of a good time is brunch by the water or dancing to ABBA in the warm night air. When she leaves me today, she’s off roller-skating. “I’m 100 per cent a girls’ girl. And I’m a gays’ girl as well,” she says. “I just need to start attracting great men!”

I’m curious about where she gets her dopamine these days. Henderson says she meditates every night – not in a half-lotus pose, but lying still in bed – and takes long baths up to three times a day. Still, dealing with dark feelings – without drugs or alcohol – has been testing. “When you can’t be off with the fairies to avoid a difficult time in your life, it’s hard. But you know what, it’s good, because it forces you to sit in it and process it, and learn to heal.”

With daughter Kitty, now 13, who encouraged her to be honest about her troubles.Credit: Courtesy of Jackie Henderson

She likes that she’s passing these lessons on to Kitty. Henderson was petrified to let her daughter know the extent of her troubles, but ultimately found a night together on the couch to explain it all, during which her “old soul” daughter encouraged her to be honest with the world. “I don’t know how it would have been if Kitty felt differently,” she says. “I don’t think I would have done the book, to be honest.”

The level of detail, she adds, felt like an obligation to the autobiographical process: “Don’t do it in the first place unless you’re prepared to share it all.”

Are there any reservations about creating a new identity for herself as “Jackie O, broadcaster and recovering addict”? Is she ready to be an advocate? “I can only speak to my experience, because my addiction is so different to anyone else’s,” Henderson notes. “But people can ask me anything they want, and I’m OK with that. I brought this up, I put it out there myself, so I’m well and truly OK talking about it. I’m excited that I can be more authentic than I’ve ever been.”

She’s excited, too, by a distant yet persistent pipedream of launching her own rehab centre. She already knows how it would look and feel. Modest rooms, surrounded by nature. Somewhere for everyone, not just the one per cent. Henderson sees plots of land now and then – 20 hectares of rolling bush, south-west of Sydney – and wonders whether such ambition is folly.

Right now, though, her focus is on speaking. She’s become almost evangelical about how shame grows when buried in silence, and how it diminishes, and softens, then ultimately disappears, when the truth is spoken aloud. “Who cares if someone judges me?” she concludes, shrugging and smiling widely. “I’m tired of burying the parts of me that aren’t perfect in everybody’s eyes.”

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