From 'sugar daddy' blackmail attempt to knife-point robbery, Jesse Kirkwood admits to 'inept' crime spree

The bizarre crime spree of a man living in a “fantasy world” included the 30-year-old pretending to be a young woman to lure a man he met on a ‘sugar daddy’ website to an isolated place to try and blackmail him.

Over several weeks in 2021, Jesse Christopher Kirkwood menaced and terrorised four “complete strangers”, Crown Prosecutor Sofia Janackovic told the ACT Supreme Court on Wednesday (20 April), describing him as a “self-interested extortionist”.

As part of what she called a “romantic deception”, Kirkwood began messaging a man on a dating website that aims to match older ‘sugar daddies’ with younger women while pretending to be a woman called ‘Stephanie’ who was in her 20s.

The man arranged to meet ‘Stephanie’ at a car park in Duffy, but when he arrived, he was surprised by Kirkwood and two others, with dashcam footage screened to the court showing Kirkwood pulling out an orange-tipped water pistol and spraying his car with water.

The man fled in his car and was chased by Kirkwood, who texted him, urging him to “make a deal” with them or he would go to the police, also telling the man he had his mother’s address.

When Kirkwood later spoke to police, he told them he was “the world’s greatest catfish” and “a more convincing teenage girl online than a teenage girl”.

But also that July, he hired a BMW using his own name and number and messaged a 17-year-old boy asking to buy vapes off him.

When they met up, the teen got into Kirkwood’s car, but Kirkwood took off and robbed him at knife-point with a co-offender, stealing $700-worth of vapes.

The spree didn’t stop there. That year, the now-21-year-old Keona Rosalie Watson thought there was an apparent “hit” out for a man she knew, and in August, she entered into an agreement with Kirkwood that he would kill this man for money.

Watson told Kirkwood she knew where he might be able to find him and they exchanged messages, in which Kirkwood made comments like, “I want to do the hit tonight” and “I’ll half [sic] the bounty with you”.

“You’ll have to plan the hit to be precise, wouldn’t you?” she asked.

“I’m a professional,” he replied

Kirkwood and another co-accused went to a house in Chapman, where a resident was friends with the man, and told a housemate to give them $25,000 or they would kill the person they were looking for.

“I’m a professional kidnapper and I’ll kill someone for a certain amount of money,” Kirkwood said to the housemate during the ordeal.

Eventually, they took $2000 from the housemate and Kirkwood burgled the house twice, stealing over $11,000-worth of items the first time and $2000 the second some days later.

Paul Edmonds of Canberra Criminal Lawyers said his client had been smoking a “very large” amount of cannabis at the time, being one ounce a week, and “may well have been living in some sort of fantasy world”.

He said the messages Kirkwood sent to Watson were concerning but were “gangster talk”, made “simply to big-note himself to a younger female co-offender”, and very little of what he said to her could be taken as fact.

Mr Edmonds also said despite the number of offences in this crime spree, it was “abundantly clear” he was not a sophisticated criminal, “or frankly very good at it”, with a number of the offences being “particularly inept”.

“These are not the actions of a hardened criminal or someone who has carefully planned the offences and is thinking clearly about their actions,” he said.

Justice Geoffrey Kennett adjourned the matter to 9 May. Kirkwood, who has been in custody since he was refused bail in August 2021, has pleaded guilty to charges including attempted blackmail, assault, aggravated robbery, aggravated burglary, theft and making a demand with a threat to kill.

Watson pleaded guilty to charges of making a demand with a threat to kill by joint commission and being knowingly concerned in an aggravated burglary over her role.