Following his prison release the man has frequently pursued women for dates, a court was told, despite suffering an extreme personality disorder and level of institutionalisation which may put him at risk of reoffending.
The man, the nation's youngest convicted murderer known for legal reasons as SLD, spent almost two-thirds of his life in jail after abducting and fatally stabbing his three-year-old neighbour Courtney Morley-Clarke on the NSW Central Coast in 2001.
After his sentence expired, he was subjected to an extended supervision order that banned him from associating with children because he posed a high risk of committing a violent or sexual offence.
A court found the child killer breached the orders when he approached a mother and her partially undressed child at a beach in Wollongong in 2023.
He was handed an 18-month jail term that expired in April for the breach.
Now 39, SLD faced the NSW Court of Criminal Appeal on Wednesday in a bid to quash the conviction, arguing it was erroneous to conclude he had associated with a child.
He had approached the mother while she was dressing her toddler near an outdoor shower at Bulli Beach and asked her how to turn the foot tap on, the court was told.
The killer then proceeded to ask the woman a series of questions about her son, including commenting on his physical appearance.
"Is dad around?" he asked the mother.
When she responded in the affirmative, SLD commented "that's good, I guess" and wandered off.
There is no evidence of any attempt to engage with the toddler at all during the exchange, even through non-verbal gestures, the killer's lawyer Nicholas Broadbent SC said.
"The conversation was at no stage directed towards the child and at no stage is there any evidence of there being any interaction with the child, physical or otherwise," he said.
Although the toddler was the subject of the conversation, Mr Broadbent contended the evidence suggested he may have intended to ask the woman out on a date.
The court was told SLD had frequently approached women and often asked them out on dates, something which was allowed under the conditions of his release and sanctioned by supervising authorities.
Mr Broadbent argued the purpose of conditions such as those placed on SLD are to protect the community, but also to allow a person who has completed their sentence to engage with and reintegrate into society.
The child killer's mere proximity to the toddler was not enough to satisfy the association condition of the supervision order, the barrister said.
Crown prosecutor Stephanie Lind argued that given the conditions were intended to protect children they should be understood to exclude SLD from intentionally approaching a child regardless of whether they were alone or in company.
She argued that if you were standing with two people, but only talking to one, you would still be considered to be with that other person.
Ms Lind also noted SLD was identified in the original judgment as having a severe personality disorder and high level of institutionalisation which placed him at a heightened risk of reoffending.
SLD appeared to pay close attention to the proceedings as he watched from a custody cell via audio-visual link.
He was released from jail in March 2025 only to be arrested the following month on allegations he was in possession of child-abuse material.
He only recently offered a motive for killing Courtney: to exact revenge for purported bullying by her brother.
Judgment in the appeal has been reserved for a later date.
Lifeline 13 11 14
Kids Helpline 1800 55 1800 (for people aged 5 to 25)
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
