Regan Keller Kennedy, 24, appeared in the Dunedin District Court yesterday after admitting the aggravated robbery and being a party to a burglary which took place last year.
On April 1, the defendant used an online profile, calling himself "Bella 77523", advertising sex for $100 an hour.
Kennedy messaged the victim and agreed to a price of $60, directing him to a Brockville address.
The man parked up at the agreed spot and sent messages to "Bella" saying he had arrived, awaiting her instructions.
Instead, Kennedy entered the car, pushed the victim against the driver’s seat and brandished a knife.
"Give me the money, bro," he said.
When the man tried to move the weapon away, his vehicle rolled forward into a parked car.
After driving around the corner and parking up again, he told Kennedy he would give him $20.
The defendant took the cash and apologised.
He was "doing this for his kid", he said.
The victim said he now felt anxious in public.
"The presence of a knife caused him to fear for his safety and has opened his eyes to how dangerous society has become," Judge Michael Turner said.
The lead-up to the incident showed clear premeditation.
"You were online pretending to be a female.
"It’s hard not to draw the inference you were luring the victim to a site with the intention of robbing him," the judge said.
Shortly after being charged, police also laid a charge of burglary against Kennedy, relating to a break-in that happened nearly a year earlier.
The court heard the defendant had been drinking with a friend in Mosgiel when they discussed potential targets.
Kennedy suggested a Hawkesbury Village butchery, established by his late father, a place where he had previously worked.
He provided details of the premises and within hours the associate was heading north.
The man broke in through a rear window and returned to Mosgiel with the till — containing $400 — and $2000 of meat.
None of the stolen goods were recovered.
The judge called it "an enormous breach of trust" and criticised Kennedy’s letter to the victims in which he said his involvement was only "giving someone a thought".
"You did much more than that," Judge Turner said.
Kennedy’s criminal history over the past four years featured another aggravated robbery, weapons offences and violence.
Counsel Andrew Dawson said his client, who had been addicted to methamphetamine since 18, was now motivated to get clean.
The judge, though, took the claim with "a large grain of salt".
"Recent history shows you completely thumbing your nose at all the offers of rehabilitation which the court has provided through its sentences."
Kennedy was jailed for 25 months and ordered to pay $3900 reparation.
