Kyle and Jackie O to reunite — in a courtroom

Nathan Jolly

April 8, 2026 9:56

Kyle and Jackie O to reunite — in a courtroom

Kyle and Jackie's case management hearings are schedule for the same court session in front of the same judge

Kyle Sandilands and Jackie “O” Henderson are both scheduled for the same court session later this month, according to the Federal Court registry.

Hearings for Sandilands and Henderson are set for Friday 24 April at 10.15am, to be heard before Justice Angus Stewart.

Although the pair have filed suit against the same employee — Commonwealth Broadcasting Corporation, a subsidiary of ARN that holds the Kiis broadcasting licence in Sydney — the two claims cover different areas of law. Experts consulted by Mumbrella say it is extremely unlikely the cases will be merged and heard together beyond this first session.

While Sandilands is challenging the validity of his contract termination under contract law, Henderson is claiming a breach of workplace law (the Fair Work Act).

So what does the listing of these two hearings in the same court session suggest?

Victoria-Jane Otavski is a commercial litigator for Blackbay Lawyers, and an expert in commercial law, employment law, defamation law, and regulatory law. According to Otavski, the fact that both matters are being heard in the same listing could be completely incidental.

“Any matters in the Federal Court get assigned to what we call a docket judge. That docket judge is effectively charged with hearing all of the case management hearings, which is what’s coming up, and then any kind of hearings in the matter, generally up to and including the final hearing. It usually is allocated based on availability and specialty of the relevant judge.”

Victoria-Jane Otavski is managing partner at Blackbay Lawyers

Otavski said it could be completely incidental that both matters are listed together, it may be based on Justice Stewart’s availability to hear both, or “it may have been by virtue of the parties recognising that there is utility in having the same judge, by virtue of any degrees of similarity or relevance between the matters.”

Any of the parties can request to have the case management hearings heard concurrently, but Otavski said at the end of the day, it’s at the court’s discretion as to whether or not to grant this.

If, however, one of the parties requests a separate hearing, they would “have to have a fairly compelling reason to resist them if everybody else is saying yes, and if you’re opposing it”, Otavski explains.

“The situation in which you would oppose it is because there’s a degree of sensitivity or revealing some kind of information that might prejudice or implicate one or the other. So, any kind of implication between Kyle and Jackie.”

Otavski said, despite the matters both being listed for a case management hearing before the same judge on the same day, it’s almost certain they will eventually be heard separately.

“Whilst there’s obviously overlap in terms of the parties, there will be distinct issues and distinct causes of action and different factual allegations. So I think that there’s no real prospect of the two sets of proceedings being heard concurrently.

“When I say that, I mean for final hearings. So they might be in case management directions hearing dates before Justice Stewart, but then there might be divergence at a particular point in time, by virtue of any interlocutory steps that are needed to be taken in those respective matters.”

While neither Henderson or Sandilands are required to attend the case management hearings, so far Sandilands has made a point of appearing in person.

If Henderson also shows up at court on 24 April, the reunion could possibly be one of the most important gigs of their careers.

The legal background

Sandilands is claiming the termination of his contract with ARN was invalid “because the preconditions for enlivening the power to terminate … were not relevantly satisfied.”

The contract termination was premised on Sandilands having committed an act of “serious misconduct” that damaged ARN’s business, and then failing to remedy the breach within 14 days. Sandilands claims no such breach occurred and, in any case, the termination of Henderson’s contract meant he was denied a reasonable opportunity to remedy the breach.

Henderson has filed a breach of general protections provisions under the Fair Work Act, claiming the termination of her contract with ARN “constituted adverse action”, following a complaint she made about Sandilands.

She alleges that she attempted to exercise workplace rights, and that her contract was terminated because of this, in contravention of the Fair Work Act.