New details emerging from a legal battle indicate that Australian Radio Network (ARN) had previously considered pairing television personality Karl Stefanovic with radio host Jackie 'O' Henderson for a breakfast radio program.

The revelation came to light during a pre-trial hearing for Henderson's fair work action against ARN, where correspondence between network executives was presented. Henderson's lawyer, Vanja Bulut, read emails that discussed potential future roles for Henderson within the company following the dissolution of 'The Kyle & Jackie O Show' and her dispute with co-host Kyle Sandilands.

One email suggested a "breakfast show with Karl, just for Sydney only plus iHeart streaming," leading to speculation that the Karl in question was Stefanovic. The correspondence further debated whether such a show would be a national offering or exclusive to Sydney.

However, the plan for a Stefanovic-Henderson show was reportedly abandoned "for reasons unknown." Henderson was subsequently offered an afternoon show with significantly lower pay, according to her legal representative. Stefanovic was later engaged by ARN to host 'The Long Weekend' radio show alongside Eddie McGuire, though this program was discontinued after a few episodes.

The court case also involves a deleted episode of Henderson's podcast, 'Her Best Life.' ARN alleges that Henderson removed the episode, along with prior installments, in late July or early August. ARN contends that this episode, released in February, contained conversations where Henderson discussed making significant life decisions, including potential career changes and severing ties with individuals. ARN is using this as evidence that Henderson was contemplating career alterations before her public fallout with Sandilands on February 20, and had decided by February 23 to pursue a different timeslot.

Henderson's lawyers had formally complained about her workplace treatment and stated her inability to continue working with Sandilands, while expressing a willingness to remain with ARN in an alternative slot. ARN's counterclaim argues that Henderson and her company indicated they would no longer fulfill their contractual obligations.

ARN has also requested the court treat the podcast episode's removal as an admission, asserting it was deleted after ARN had already referenced its contents in legal proceedings. The Federal Court has yet to rule on the allegations from either party. Henderson's case is anticipated to go to trial in October. The court battle centers on Henderson's broadcasting contract, which ARN terminated on March 3.