Jackie 'O' Henderson's manager Gemma O'Neill looks downcast at Westfield in a pair of pyjama-style pants as former KIIS FM star wipes her contact details from Instagram

Jackie 'O' Henderson's talent manager Gemma O'Neill cut a sombre expression as she stepped out on Friday amid her highly-publicised tax bill woes. 

The businesswoman – whose Gemmie Agency owes the Australian Taxation Office over $615,000 – was spotted strolling around Westfield Bondi Junction, looking relaxed in a pair of pyjama-style polka dot trousers. 

Appearing lost in thought, the businesswoman completed her look with a brown jumper, a cross-body handbag and a pair of sandals. 

She wore her fiery hair out in natural waves and clutched her mobile phone in one hand. 

The sighting comes after Henderson, her longtime bestie, quietly removed O'Neill's details from her Instagram bio. 

It now only contains a link to buy Henderson's memoir, The Whole Truth. 

Back in May, Daily Mail reported that – according to multiple sources – Henderson and O'Neill's longtime friendship had 'cooled' in recent weeks. 

Looming in the background of this alleged chill are the legal proceedings Henderson has launched against ARN, after her services agreement to host KIIS FM's Sydney breakfast show was terminated.

As Henderson's manager and confidante, O'Neill would likely have played an advisory role during the fraught months leading up to the contract being torn up.

We make no suggestion of wrongdoing by any party and note the matter is now before the courts.

O'Neill declined to comment, while a source close to her camp also pushed back on the claims, insisting the pair still speak regularly and remain friends.

O'Neill's company Gemmie Agency entered voluntary liquidation in November. 

Administrators from Grant Thornton Australia said in a creditors' statement that the debts incurred by O'Neill's agency were in stark contrast to a seven‑figure commission paid by an unnamed 'key client' between October 2023 and March 2024, the publication reported.

On February 20, O'Neill reportedly informed the administrators she couldn't make any repayment contributions, noting she has no available personal savings, limited income, and had failed to refinance her beachside apartment in Sydney.

That was the same day O'Neill's star client Jackie O fought with her KIIS FM radio partner, Kyle Sandilands, in the infamous argument about her being 'away with the fairies', which later saw the duo taken off the airwaves permanently and their $100million contracts torn up.

Even after Gemmie Agency folded, O'Neill continued representing Henderson during difficult discussions with ARN executives in the lead-up to the broadcaster's split from longtime radio partner Kyle Sandilands. 

Henderson now remains at the centre of a Federal Court case against ARN Media over the termination of her reported $100million contract.

Court documents, filed as part of Henderson's statement of claim, outline months of internal tension leading up to the dramatic breakdown of the Kyle and Jackie O Show earlier this year.

According to the filings, Henderson raised concerns about Sandilands' on-air behaviour with KIIS network management months before the relationship publicly deteriorated during a live broadcast in February.

It follows reports that Jackie struggled with the glamorous 'hot blonde' image crafted around her by executives and publicists.