An Illawarra career criminal had been out of jail on parole less than a month in 2017 when he held up two businesses in as many days - one while armed with a knife - and threatened employees who tried to stand in his way.
Ian Hammond landed a haul of cash, drugs and an expensive watch between robberies at the Flinders Save and Deliver Pharmacy on June 12 and Warrawong Cash Converters on June 14.
However, the relatively meager spoils have ended up costing the 47-year-old dearly: Hammond was sentenced to an overall jail term of six years and three months in Wollongong District Court on Friday.
Judge Andrew Haesler set a generous non-parole period of three years, noting Hammond was largely institutionalised, having spent every birthday behind bars since the age of 20.
He said Hammond would need significant assistance on extended parole if he was going to have any hope of living a law-abiding life, given his history of repeat offending.
Court documents said Hammond was arrested late at night on June 14 after police recognised him in high-quality CCTV footage from the Cash Converters robbery earlier that evening.
Workers at the pawn shop told police Hammond came into the store with his face partially covered by his jumper and said "this is a robbery, where's the money?"
He then jumped the counter, opened the cash register with a key and took almost $1000 before jumping back over the counter, threatening to "shoot" two works and running from the store.
Meanwhile, police also linked Hammond to the chemist heist two days earlier, claiming he had robbed the pharmacist at knife-point of cash, oxycodone, valium and his watch.
Hammond subsequently admitted to carrying out the Cash Converters hold-up - the CCTV was too clear to dispute - however denied responsibility for the pharmacy.
The chemist case proceed to trial in July, with the jury finding Hammond guilty.
Judge Haesler remarked on Friday that Hammond had been entitled to exercise his right to trial in the chemist robbery case, regardless of how "objectively hopeless his defence was".
In sentencing Hammond, he noted the terrible impact armed hold-ups can have on individual victims and the community.
"I'm prepared to find his crimes were opportunistic but that's little comfort to the staff that were left in fear," he said.
The court heard Hammond had had a disadvantaged upbringing fraught with violence and had begun taking drugs at an early age, leading to his spiral into crime.