Court documents reveal telling sign Jackie 'O' Henderson's friendship with ex-KIIS FM newsreader Brooklyn Ross is over - amid rumours of a rift with her manager and a new eastern suburbs bestie

Jackie 'O' Henderson appears to have taken a swipe at former colleague Brooklyn Ross amid her legal battle with Australian Radio Network (ARN).

The former radio star, 51, and newsreader Ross, 38, developed a close friendship over 11 years working together, but it now seems their relationship is over.

According to court documents, Henderson specifically named Ross, alleging he and other staff did not 'intervene' during her infamous on-air clash with Kyle Sandilands on February 20.

This claim came in response to an amended defence lodged by ARN on September 1.

In the amendment, the network stated that 'in the course of Mr Sandilands' comments, Brooklyn Ross, an ARN employee, attempted to intervene on multiple occasions'.

The defence also claimed that several other employees checked in on Henderson after she left the studio following her argument with Sandilands.

However, Henderson and her legal team have since filed a response to the amended defence, lodged on September 8, denying that Ross ever tried to stop Sandilands from 'bullying' her during their final show together.

'As to paragraph 28(b)(v) of the Defence, the Applicants deny that Brooklyn Ross, ARN employee, or any other staff member present, attempted to or did successfully intervene in Mr Sandilands' bullying and other unwanted conduct towards Ms Henderson on 20 February 2026,' the response read.

Despite this, recordings of the heated exchange between Sandilands and Henderson in February reveal that Ross attempted to mediate between the pair on the day.

During the disagreement, Sandilands said Henderson's fascination with astrology had made her 'almost unworkable', prompting Ross to respond: 'It's not that bad, Kyle.'

As tensions escalated, Ross added, 'I think there is a middle ground between the two of you,' before Henderson cut him off to continue her argument with Sandilands.

Ross intervened again a few minutes later when Sandilands claimed that 'everyone' at KIIS FM had been complaining about Henderson behind her back, leaving the radio star emotional over the revelation.

'Kyle, hang on, it's hard to say that someone,' Ross began, but Sandilands cut him off, telling the newsreader to 'wake up'. 

The singling out of Ross in court documents may spell the end of his friendship with Henderson, despite the pair maintaining a close bond for more than a decade, one which seemingly survived the collapse of The Kyle & Jackie O Show. 

Ross had previously described Sandilands and Henderson as his 'radio family', with his and Henderson's friendship extending outside of work.

Henderson and Ross were seen spending time together during a highly publicised trip to New York in 2024, and Henderson also attended his wedding in Las Vegas to husband Damien Dirienzo.

In August, Ross also revealed that he called Henderson to seek her thoughts on him leaving KIIS FM to work with Sandilands once more on his Kyle Sandilands Live project. 

He admitted on The Kylecast, a new series claiming to be an 'unofficial fan podcast' of Kyle Sandilands Live, that he had a 'tough' conversation with Henderson about his career move.  

'It was tough… just because I didn't know what her reaction [would be], and she is such a great friend of mine and we're so close,' Ross told host Bella Frizza.

'But she came back and said she's supportive of my career, and if that was where I thought was the best option, she could see why… she said, you know, "Go for it."'

Ross also found himself caught in the middle last month when Sandilands discovered Henderson had accused him of causing her post-traumatic stress disorder (PTSD).

Sandilands blasted the claims she made in court as 'fake' and said she had betrayed him.  

'It has rattled my trust in humans for the rest of my life,' he said. 

However, Ross became emotional over the revelation and Sandilands 'shattered' response to it, saying: 'It's terrible you two are in this position against each other. She doesn't hate you that bad, Kyle.' 

Henderson's friendship with Ross may not be the only casualty of the debacle. For weeks, Inside Mail has reported on rumours of a rift between Henderson and long-time manager and 'bestie' Gemma O'Neill. 

While O'Neill has denied the rumours, calling them 'inaccurate' and 'ridiculous', it can't be denied that Henderson's friendship circle appears to have changed drastically amid the ongoing Federal Court battle with ARN. 

Her social media accounts may have remained silent in recent months, but that hasn't stopped her from spending time with her new best friend, Pip Edwards.

Henderson has seemingly embraced her role as an eastern suburbs socialite, recently pictured at a luxury Sydney Harbour home during a skincare launch featuring breathwork, sound healing, astrology readings, and massages.

The former radio star was seen wearing a facemask and designer sunglasses while seated on a workout mat alongside Edwards.

Also in attendance were model Simone Holtznagel; Aussie Home Loans heiress Deborah Symond O’Neil; Lou O’Neil (sister-in-law to recent Daily Mail fixture Poppy Tzaneros); entrepreneur Alyce Tran; and Barbara Coombes (née Tzaneros).

They were joined by Pilates queen Bernadette Sukkar; Lisa Wipfli (wife of radio star Michael 'Wippa' Wipfli); jeweller Olivia Bond; luxury fashion PR guru Billy Mitchell; model Natasha Oakley; and high-society couple Alex Porter and Chris Ledlin.