Just before 10.30am on Monday, the ex-Steelers boss leaned over the dock in a near-empty courtroom at Wollongong to give his teary mother a kiss on the cheek and his brother one last, heartfelt hug before he was led away by prison guards.

The next time the Miles family sees their son and sibling, it will be during regulated visiting hours at one of the state’s 36 correctional or remand centres.

Miles will be wearing a green tracksuit and white Dunlop Volleys – the standard dress for prisoners across the state. His guests will have to go through a series of security checks before they can see him and then the entirety of their interaction will be monitored and recorded on surveillance cameras.

It’s a far cry from the comfortable surrounds to which Miles had become accustomed while living with his family in upscale Barden Ridge, in the Sutherland Shire, funded in part by the salary afforded to him as the club’s trusted general manager for more than a decade.

But a faithful servant to the club, Miles was not. His insatiable addiction to gambling turned him into a thief and a liar – and the Steelers Club became his cash-cow.

Court documents reveal the since-sacked GM began siphoning money from the club in 2010, after taking out more than 11 credit cards, two personal loans and a cash first loan in a failed bid to keep pace with his betting problem. 

The missing funds, estimated at somewhere between $800,000 and $1 million, were uncovered during a company audit in 2016.

Miles managed to maintain the charade for another 12 months, relying on the trust bestowed on him by the club’s board of directors while providing a host of false explanations behind the missing cash.

But by early 2017, Miles knew his time was up and confessed all to the head of the board one morning in late January.

He was subsequently charged with dishonestly obtaining financial advantage by deception, to which he pleaded guilty.

In court on Monday, Judge Andrew Haesler said it was Miles’ early guilty plea, coupled with his obvious remorse and commitment to repaying the outstanding money that allowed for a reduced sentence, however said nothing other than full-time prison was appropriate.

“The sentence must reflect justice for the offender as well as justice for the community,” Judge Haesler said.

He set an overall sentence of four years jail, which included a 25 per cent discount for the early guilty plea.

Miles will be eligible to apply for parole in December 2019 after serving a minimum term of two years.