While both sued their former employer ARN, that’s where the similarities end. Kyle Sandilands, ever the showman, turned up at every court hearing in his Rolls-Royce. Jackie ‘O’ Henderson, whose lawyers said she did not want to share a room with Sandilands after his abusive on-air tirade in February immolated their relationship, has kept a low profile.

Desperate to get back on air, Sandilands has cut a $12 million deal with his old network. Henderson, whose own $82 million claim for unlawful dismissal continues, has not spoken with the company in months, meaning the matter remains destined for a court showdown in October.

Kyle’s new show launches next week, and he has been doing the media rounds in advance. Henderson has more or less let her legal team do the talking.

Among the points raised by Henderson’s lawyers was the claim made, back in April, that they would provide evidence from two medical experts documenting the psychological impact of Sandilands’ treatment of her.

While eating Big Macs in the aforementioned Rolls-Royce with a scribe from our stablemates at The Australian Financial Review, Sandilands responded to that by casting doubt on the professional qualifications of Henderson’s medical expert before trying to characterise the exchange as off the record.

CBD is not suggesting that any of Henderson’s witnesses have been subject to such professional censure.

It did, however, get us wondering about those medical experts.

One expert, whose assessment of Henderson will be in the mix, is Dr Justine Corry, a self-described “inner success coach”, whose work involves helping high-achieving women “ditch emotional blocks, reclaim their power and thrive in every area of life”, according to her LinkedIn page.

As for Dr Corry’s credentials, she describes herself as a “former clinical psychologist”, and has a PhD, but does not appear on the Australian Health Practitioner Regulation Agency’s list of current practitioners.

Corry would, however, be familiar to listeners of the late Kyle and Jackie O show, appearing on air in 2024 to give Sandilands his “first therapy session”, during which he mentioned his abandonment issues caused by a difficult childhood.

“They’ll [your emotions] just pop out in other ways,” Corry told Sandilands. “Usually in anger, actually.” Evidently, she was onto something.

Corry is also close with Henderson and her long-time manager and best friend Gemma O’Neill. In a glowing testimonial on Corry’s website, Henderson said that she had “changed my life in a profound way”.

“I never realised how deeply my unhealed wounds and ingrained schemas were shaping my choices until we began this journey together.”

O’Neill told CBD via text that the parties had engaged their own independent psychiatrists to give evidence in the matter, however, it is understood that Corry’s professional coaching work with Henderson will also be used in her legal case against ARN.

Corry was a regular guest on Her Best Life, a podcast hosted by Henderson and O’Neill as part of their “Besties” events and lifestyle joint venture.

More recently, Corry delivered a “powerful women’s coaching session” at the $3199-a-head weekend wellness retreat organised by Henderson and O’Neill and headlined by Meghan, Duchess of Sussex, who drew criticism for only spending two hours at the event. Corry did not respond to requests for comment.

Meanwhile, questions remain about O’Neill’s own talent management business Gemmie Agency, which collapsed into administration late last year owing the tax office more than $500,000. Central to liquidator Grant Thornton’s inquiries is an invoice worth about $1 million for a single, nameless client in late 2023.

According to the liquidator, only about $254,000 of the invoice was received by the company, with a further approximately $788,000 applied against O’Neill’s director loan.

No word on the identity of the talent that provided the invoice, although we do note that the agency brought Gwyneth Paltrow to Australia for an event organised for O’Neill and Henderson’s Besties network around that time. No word either on why that money went to a director’s loan, and why the business collapsed the way it did.

Will Henderson follow Kyle’s lead and settle with ARN? Well, the company is prepared to see this all the way, releasing a statement to the market on Monday responding to “recent media commentary” by noting that “it is progressing evidence with the intention of vigorously defending all claims”. But we know how quickly these things can change.

Everything is Connected

On the subject of Kyle Sandilands’ new show, it is already getting a bit of love from the political class despite all the unsavouriness that lingers from the Jackie O meltdown.

NSW Premier Chris Minns, every conservative’s favourite Labor man, is set to appear on the first show.

Minns has kept rather busy himself over the past few months. A release of the premier’s diary for the June quarter revealed a few interesting meetings, including a geopolitical briefing with US general David Petraeus, a former boss of the CIA. Also attending were Treasurer Dan Mookhey and Corrections Minister Anoulack Chanthivong.

Also on his dance cards was a catch-up with storied advertising man John Singleton and Singleton Group Chief Executive David Norris.

A week later, Norris and Singleton were spotted at power dining hotspot Grill Americano for a long lunch with colourful nightclub identity John Ibrahim and Sandilands, celebrating the shock-jock’s settlement in his legal battle with ARN. As we like to say in these parts, everything is connected.