How radio star Jackie ‘O’ Henderson’s stalker walked away with $50,000 after being jailed and sacked from his Sydney ports job

The man jailed for stalking former radio queen Jackie ‘O’ Henderson has had a huge win in court, walking away with $50,000 after being unfairly dismissed from his job.

David Gourlay won a major unfair dismissal victory in April after sending a resignation letter to his employer while in a state of ‘mental confusion’.

Now, the ex-stevedore, 38, has been compensated $49,728, plus superannuation, by his former employer Sydney International Container Terminals Pty Ltd (Hutchison Ports).

According to court documents seen by the Daily Mail, Gourlay pushed to be reinstated to his old job, but Fair Work Commission (FWC) Commissioner Damian Sloan rejected the remedy, saying ‘it is not appropriate to order that Mr Gourlay be reinstated’.

‘I have determined that it is appropriate in all the circumstances of this case that Mr Gourlay receive compensation equal to the difference between the earnings he would have derived had he remained employed by Hutchison Ports during the anticipated period of employment, and the remuneration that he earned from other work or employment in that period,’ he added. 

‘That is a figure of $49,728, plus superannuation.’

‘I will order that Hutchison Ports pay Mr Gourlay $49,728, less taxation as required by law, plus 11.5% superannuation,’ Sloan added.

Hutchison Ports is required to pay Gourlay the amount by September 25. 

The Daily Mail has reached out to Henderson for comment.

In April, the Courier Mail reported that Gourlay sent a resignation letter to Hutchison Ports’ HR department at 4.31am on September 26, 2024.

The company accepted the resignation at 11.02am; however, Gourlay sent a follow-up email later, stating he had changed his mind about leaving.

The publication reported that Gourlay later argued before the FWC that he never intended to resign and was suffering ‘paranoid delusions’ at the time.

While Gourlay did not indicate to his employer that he was suffering mental health issues at the time, colleagues reportedly expressed concerns to management on the day of his email, later that afternoon.

The Maritime Union of Australia subsequently escalated the matter, formally requesting that Gourlay be permitted to rescind his resignation, which Hutchison rejected.

Gourlay then took his case to the FWC, asking to be reinstated in his old job.

However, FWC Commissioner Sloan rejected the request, ruling in March 2025 that there was no dismissal, despite finding that Gourlay was in a state of ‘mental confusion’ when he sent the email.

The matter escalated again to a Full Bench hearing which found, in December, that Sloan had made an ‘appealable error’ in his judgment by ‘failing to consider events after the resignation email had been accepted’.

The bench did not make a ruling on the case, but rather passed it back to Sloan to reconsider.

In April, Sloan reversed his decision, ruling that Hutchison did not make appropriate enquiries into Gourlay’s condition.

‘Mr Gourlay had nearly eight years’ service. I accept that it was not without its issues, but it was harsh for Hutchison Ports to purport to treat Mr Gourlay’s resignation as legally effective and accept it,’ Sloan said.

Despite the reversal, Sloan also expressed concerns about Gourlay’s fitness to resume work, stating he had ‘insufficient evidence’ to rule on reinstatement and instead ordered another hearing.

Gourlay was sentenced to 16 months in prison for stalking Henderson, 51, in December.

Over a five-month period, he sent her up to 2,000 Instagram direct messages, many arriving in rapid succession and referencing private details about her life.

In the delusional narrative he constructed, Gourlay even claimed the pair shared a child.

Sydney’s Downing Centre Local Court heard that Gourlay has schizoaffective disorder with bipolar features, and that his belief he was in a relationship with Henderson arose from severe delusions.

His lawyer, Trudie Cameron, told the court her client had been struggling significantly and had not been taking his prescribed medication.

He had reported hallucinations and paranoia in the period leading up to the barrage of messages.

An expert report linked his conduct directly to his mental health condition, with the court hearing that the offending occurred entirely within the context of his delusion.

Cameron stated that, when stabilised on medication, Gourlay functions well within the community.

She argued that he should be allowed to serve his sentence in the community, emphasising his remorse and his awareness of the effect his behaviour would have had on Henderson.

The prosecution, however, submitted that Gourlay should be imprisoned, describing the sexualised messages as ‘abhorrent’ and stressing the need to send a clear signal of deterrence.

Deputy Chief Magistrate Theo Tsavdaridis said the content of the messages was extremely concerning and that Henderson’s fear for her family’s safety was entirely justified when Gourlay appeared near her home.

He also noted that Gourlay already had a lengthy criminal history and had been serving two community-based orders at the time of the offending.

Gourlay was sentenced to 16 months in prison, with a non-parole period of eight months.

Taking into account time already served, Gourlay was eligible for parole in March this year.

A five-year apprehended violence order was also put in place, preventing him from contacting Henderson in any way except through a lawyer.

The order, which expires in 2030, bars him from assaulting, threatening, stalking or harassing the radio presenter or anyone with whom she has a domestic relationship.