It has been more than five years since the son of AFL legend Robert “Dipper” DiPierdomenico fleeced $140,000 from his employer.
Dylan DiPierdomenico has not paid a cent back to the family-owned golfing business since he was dismissed in 2019.
A judge found this "troubling" as he decided to throw the 42-year-old old behind bars for nine months on Thursday.
"You've had five-and-a-half years to repay some of the money that you obtained dishonestly," Judge Richard Maidment told him.
"I was told you haven't had the opportunity to do that because of legal fees.
"A more clear link between that and remorse would've been to see you put their priorities ahead of your own."
DiPierdomenico admitted 71 instances of fraud over 10 months between August 2018 and June 2019, while he was national sales manager for golfing wholesaler MGI Golf.
He created fake PayPal accounts and fabricated invoices to get customers to put money into his personal bank account.
His fraud was uncovered by managing director Carrie Edwards-Britt while she was going through the company's accounts.
When she confronted DiPierdomenico about anomalies she had discovered, including a golf buggy he put through as $0, he admitted stealing from the company.
He claimed he had taken $10,000 to fund his gambling addiction, when the true figure was 14 times that amount.
"I'm really sorry, you've done so much for me," he told Ms Edwards-Britt.
Ms Edwards-Britt, whose father had started the business, said DiPierdomenico had manipulated her family and thought he could get away with it because they trusted him.
"He abused our trust, good nature, used our business as a place for him to profit from without any consideration for the people he was hurting," she told Melbourne's County Court on January 20.
"I was in damage control with our customers ... who had been caught in Dylan's web of lies and deceit."
She claimed DiPierdomenico's father told a mutual friend "he didn't understand why we were so upset because it was just money".
Judge Maidment was critical of DiPierdomenico's abuse of trust, in one of few senior positions at MGI Golf not held by a family member.
"Each gambler thinks that the next big win is going to get them out of jail effectively and cover the tracks of dishonest conduct," he said.
DiPierdomenico's barrister pleaded with the judge not to jail him as he was remorseful, the case had been delayed and he had made positive steps to address his gambling addiction through therapy.
But Judge Maidment decided the offending warranted imprisonment to deter others from engaging in similar acts.
DiPierdomenico paid about $18,000 back to the business before he was sacked in June 2019, but still owes MGI Golf $122,550.20.
Judge Maidment ordered he repay the outstanding money as he handed him a nine-month prison term with a two-year community corrections order.
DiPierdomenico, who will spend his first night in jail on Thursday, must do 200 hours of community work upon completing his term.
