The man jailed for stalking radio host Jackie 'O' Henderson has won a major payout after the Fair Work Commission found he was unfairly dismissed from his job at a Sydney ports company. David Gourlay, 38, will receive $49,728 plus superannuation from Sydney International Container Terminals Pty Ltd, trading as Hutchison Ports.
Gourlay, a former stevedore, had pushed to be reinstated to his old job, but Fair Work Commission (FWC) Commissioner Damian Sloan rejected that remedy. "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," Sloan said. "That is a figure of $49,728, plus superannuation."
Sloan ordered that Hutchison Ports pay Gourlay "$49,728, less taxation as required by law, plus 11.5% superannuation." The company must make the payment by September 25.
The Daily Mail has reached out to Henderson, 51, for comment.
How the resignation unfolded
The Courier Mail reported in April that Gourlay sent a resignation letter to Hutchison Ports' human resources department at 4.31am on September 26, 2024. The company accepted the resignation at 11.02am, but Gourlay later emailed to say he had changed his mind about leaving.
Gourlay went on to argue before the FWC that he never intended to resign and was suffering "paranoid delusions" at the time. He did not tell his employer he was experiencing mental health issues when he sent the email, but colleagues reportedly raised concerns with management later that same afternoon.
Union intervention and years of legal wrangling
The Maritime Union of Australia, which represents dockworkers and other maritime employees, escalated the matter by formally asking that Gourlay be allowed to withdraw his resignation. Hutchison Ports refused, and Gourlay took his case to the FWC seeking reinstatement.
Commissioner Sloan initially rejected the request in March 2025, ruling there had been no dismissal, despite finding that Gourlay was in a state of "mental confusion" when he sent the email. The case then went to a Full Bench of the FWC, which found in December that Sloan had made an "appealable error" by "failing to consider events after the resignation email had been accepted." The bench did not decide the case itself, sending it back to Sloan to reconsider.
Commissioner reverses his ruling
In April, Sloan reversed course, finding that Hutchison Ports had not made appropriate enquiries into Gourlay's condition before treating his resignation as final. "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 reversing his earlier finding, Sloan said he had "insufficient evidence" to rule on reinstatement given ongoing concerns about Gourlay's fitness to return to work, and ordered a further hearing. That hearing produced this week's compensation ruling in place of reinstatement.
The stalking of Jackie 'O' Henderson
Gourlay was sentenced to 16 months in prison in December for stalking Henderson, one of Australia's best-known radio presenters. Over a five-month period, he sent her up to 2,000 direct messages on Instagram, many arriving in rapid succession and referencing private details about her life. As part of a delusional narrative, Gourlay 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 stemmed from severe delusions.
Court hears of untreated mental illness
His lawyer, Trudie Cameron, told the court her client had been struggling significantly and had stopped taking his prescribed medication before the offending. He had reported hallucinations and paranoia in the lead-up to the barrage of messages. An expert report linked his conduct directly to his mental health condition, with the court told the offending occurred entirely within the context of his delusion.
Cameron said Gourlay functions well within the community when stabilised on medication, and argued he should serve his sentence in the community, pointing to his remorse and his awareness of the impact his behaviour would have had on Henderson. Prosecutors argued for imprisonment instead, describing the sexualised messages as "abhorrent" and stressing the need for a clear signal of deterrence.
Sentencing and ongoing restraining order
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 after Gourlay appeared near her home. He also noted Gourlay's lengthy criminal history and that he was already 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 time already served into account, he became eligible for parole in March this year. A five-year apprehended violence order was also imposed, barring him from contacting Henderson except through a lawyer and from assaulting, threatening, stalking or harassing her or anyone in a domestic relationship with her. The order runs until 2030.
