Jackie 'O' Henderson slaps ARN with an additional $3 million claim after taking loan from the network as she battles over $100 million contract

Jackie 'O' Henderson is seeking an additional $3million as her court battle with ARN rages on. 

The former Kyle and Jackie O Show star is warring with the radio network over the termination of her $100million contract, but has now filed for a repayment of a loan agreement, news.com.au reports. 

In documents filed in Federal Court on Tuesday, Henderson claims her former employer breached a $3million agreement, under which shares in the company were bought on her behalf.

'It was an express term of the Agreement that CBC would provide Henderson Media with a limited recourse loan equal to $3,000,000 for the purpose of purchasing ordinary shares in ARN,' the amended statement of claim filed with the court by Henderson's lawyers explains. 

Henderson's lawyers say she entered into an agreement with ARN in October 2023 for a loan to acquire ARN ordinary shares, and that ARN was only entitled to sell the shares on behalf of Henderson and her company, Henderson Media, if she terminated or breached the agreement. 

Lawyers for the radio star allege that on April 29, ARN sold the shares to repay the loan, declaring that a 'bad leaver' event had occurred.

'(The company's solicitors) did not describe the basis on which the Board of ARN had determined that a "bad leaver" event occurred,' Henderson's lawyers said. 

Henderson claims she did not terminate or breach the loan agreement, and seeks compensation, alleging that ARN breached the deal. 

It follows news that Henderson will be forced to undergo a medical examination as part of her legal action against the Australian Radio Network (ARN). 

According to court documents released on Thursday, the examination is 'to be conducted by a suitably qualified medical expert to be selected by' ARN.

The radio host's former employer is then required to file an affidavit from their chosen expert on August 6, reported The Daily Telegraph on Friday.

Henderson, 51, launched a Fair Work claim against ARN in April after her radio contract was torn up following a heated on-air argument with ex co-host Kyle Sandilands.

She has alleged that ARN failed to provide her a safe workplace and minimise the psychosocial risks after she made several complaints against Sandilands.

Her camp confirmed this week they will continue with the court case, despite Sandilands recently settling with ARN for $12.09 million. 

Henderson's bid for an $82 million payout is now facing renewed scrutiny, with insiders suggesting she could walk away with less than Sandilands if she settles.

Sandilands' reduced settlement, which includes $1.5 million in advertising contra, has reset expectations around what ARN may be willing to pay as Henderson continues her Federal Court fight.

The shock jock's payout is understood to reflect roughly a year's salary under his contract, which reportedly included a multimillion-dollar base fee plus a $1 million sign-on bonus and a $3 million one-off fee.

Henderson's contract with ARN may not include such add-ons, meaning that if she does settle, her payout would more likely land between $7.5 million and $10 million.

Henderson is suing ARN for wrongful termination, alleging her dismissal contravened the Fair Work Act.

At the centre of the dispute is ARN's claim that Henderson herself initiated the end of The Kyle & Jackie O Show after raising 'psychosocial health and safety and bullying complaints' about Sandilands.

Henderson has rejected this, insisting she did not resign despite ARN previously stating she had given notice she could no longer work with her co-host.

The two sides also remain at odds over whether an alternative program was ever offered to Henderson, a claim her legal team denies.