The Canberra man whose criminal record reads like a "Greek tragedy" will spend more time in jail for selling methylamphetamine to a cop.
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Matthew Massey, 40, has spent more than two decades behind bars.
He was arrested again in 2013, one of 60 people arrested and charged as a result of an investigation into the supply of prohibited drugs.
On the day his trial was due to begin, Massey pleaded guilty to selling 7.2 grams of methylamphetamine to a police officer.
Justice Richard Refshauge convicted him on Monday of trafficking and sentenced him to two years and one month in prison, starting February.
He imposed a non-parole period of 13 months, to expire in March 2017.
Earlier, lawyers for Massey had argued he deserved another chance to redeem himself after spending more than two decades behind bars.
Justice Richard Refshauge on Monday acknowledged the difficulty he faced in sentencing Massey, given his lengthy criminal history, and accepted "massive amounts of jail time" would not be in his favour.
He asked Massey's defence barrister Alyn Doig: "How do we address this?
"The fact is, he's been unable to stop committing serious offences, in some cases very serious offences.
"It's just Greek tragedy."
Mr Doig said Massey was well known to the court and wider community, but he urged the judge to consider the objective seriousness of the single offence in sentencing.
He pushed for the judge to consider a suspended term of imprisonment.
"Society has a responsibility, the system has a responsibility to Mr Massey and he has not been assisted in this situation ... Mr Massey is not the devil incarnate."
"He's been a very bad person over a long period of time but he's not beyond redemption."
Massey, who had sought help for drug addiction, told the judge he wanted to move in with his partner at Giralang if released and his number one priority was to be a role model for their baby son.
Justice Refshauge: "Do you have the strength of character to do that?"
Massey: "Yes I do, your Honour."
Mr Doig said Massey had been dating former basketballer turned drug addict Janna Sladic, who died from a suspected heroin overdose last year, around the time of the offence and was well aware of her fate.
"He's not stupid, your Honour. He's not clever, but he's not stupid.
"He's looking for some mercy to be tempered here, if your Honour pleases."
Mr Doig said his client regretted the waste of life his time in jail had been and knew he faced his last chance to turn his life around.
"He's got a decision to make: Is he going to work hard to stay free and clean, or is he going to go back and die in prison?"
Prosecutor Katrina McKenzie said Massey's long history of violent offending showed his prospects for rehabilitation were bleak.
"He has a son now, he's got two other children and they've never provided an incentive to get on the straight and narrow," she said.
"Any period in the community puts the community at risk, whether it be from dealing drugs or committing acts of violence."
