Kyle and Jackie O are finished, but The Kyle Show is just starting in court

April 24, 2026 — 3:56pm For 27 years, Kyle Sandilands and Jackie “O” Henderson’s morning radio show kept Sydney entertained and enraged. Now, Sandilands is determined to continue doing so alone, despite facing the possibility of months off-air, the probability of a lengthy and rancorous trial, and the near certainty that Australia’s most lucrative commercial radio partnership of the modern era is finished. Broadcaster Kyle Sandilands departs the Federal Court on Friday afternoon. Sam Mooy Sandilands was thronged by the media as he left court. Sitthixay Ditthavong Sandilands enters his Rolls-Royce, which has an estimated value of near $1 million, after a bruising hearing. Sam Mooy His new production was on full display outside the Federal Court on Friday , where his and Henderson’s lawyers were hashing out details of their cases against radio company ARN over the pair’s cancelled $100 million, 10-year contracts. It is uncommon for parties to litigation to appear at such case management hearings, the preliminary skirmishes in which lawyers iron out arid procedural details ahead of the main trial. But Sandilands has appeared at both of these hearings so far, ferried to and from Friday’s hearing in his circa million-dollar Rolls-Royce Phantom with number plate KS20 and giving an excited media scrum (at one point two cameramen inadvertently tackled each other) exactly what they wanted. When he made it to the courtroom, dressed in a form-fitting blue suit with a pink windowpane pattern, Sandilands was seated front and centre of the courtroom, eyes locked on Justice Angus Stewart. Henderson, meanwhile, has been notably absent. On Friday, her barrister, Vanja Bulut, told the court that she did not want to put her client in the same “enclosed space” as Sandilands, who “she says has caused a significant psychological harm”. She is expected to call on medical experts to outline the impact the dispute has had on Henderson’s mental health and wellbeing. This whole dispute all began because in February, Sandilands launched into a nasty, seven-minute on-air tirade attacking Henderson’s work ethic and obsession with horoscopes; the kind of rant she has endured from her male co-star on several occasions during their partnership. The pair have not spoken since, and it is hardly a stretch to imagine that Sandilands’ conduct has made his former partner feel uncomfortable about the prospect of facing him in a courtroom. “Bullshit,” was how Sandilands labelled this suggestion. “They say they don’t want to be in the same courtroom, that’s their legal strategy. We have a different strategy. Just don’t believe the bullshit that you hear and read, just wait to see what comes out in court,” he said to reporters. With that, he declared he was off home to “eat wings” with his son. Outside court, Sandilands appeared full of hubris. So it’s easy to forget that inside, he did not get what he wanted. Before the hearing, he’d told reporters that he wanted ARN to “put me back on air” in order to “get the [company’s] share price back up”. This will not happen any time soon. Stewart ruled that Both Sandilands and Jackie “O” Henderson’s legal cases against ARN over the scrapping of their $100 million contracts will be heard over the course of two weeks spanning October 12 to October 23. The radio company’s barrister, Tom Blackburn, SC, told the court that Sandilands’ demand for the judge to order his return to the airwaves was “close to hopeless”. Justice Stewart appeared sympathetic to this, noting that he was “highly unlikely” to grant an order forcing ARN to take Sandilands back on air. “That’s not necessarily true,” Sandilands said when asked about the prospect he may not work at all until the trial in October. “There are other ways to work. That’s not the only radio station in the world,” he insisted. Whether any other radio station in the would take him – given the baggage, the ongoing litigation, the complaints, the unsavoury headlines and the demanding asking price – remains doubtful. Tasteless, even. But Sandilands has made a career out of stunts that flirt with, or sometime barrel over, the line of good taste. And whatever prospects he does have of a return lie in his ability to do what he does best: court outrage. Kishor Napier-Raman is a senior business writer for The Sydney Morning Herald and The Age. Previously he worked as a CBD columnist and reporter in the federal parliamentary press gallery. Connect via X or email . From our partners