Co-conspirators described John Higgs as foolish and reckless, but still an important part of a plot to import 15 million ecstasy pills into Australia.
For his part he was sentenced to 18 years behind bars and the 74-year-old still has a little under five years to go before he's eligible for parole.
But the major drug trafficker who turned to turncoat barrister Nicola Gobbo for legal advice believes his chance at a successful appeal will be wasted if he has to serve one day more.
He filed an appeal in January against his conviction for the importation of 4.4 tonnes of ecstasy pills more than a decade ago in the infamous tomato tins bust - then the world's largest illicit drug interception.
On Thursday, he asked Victoria's Court of Appeal to release him on bail until a decision.
Higgs hasn't yet been granted permission by the court to appeal, but his barrister David Grace believes a novel appeal ground has a strong chance at success.
A prolific drug importer with a significant criminal history - including long stints behind bars for manslaughter and conspiracy to traffic amphetamines - Higgs had Ms Gobbo on a retainer, Mr Grace says.
Their lawyer-client relationship dates back to the 1990s when Ms Gobbo was working for prominent criminal lawyer Alex Lewenberg.
"She continued the association with him, recommencing in 2006 and flowing through to his arrest in August 2008," Mr Grace said.
"Lo and behold, the first lawyer that Higgs sees, who attends upon him in custody after his arrest for the tomato tins prosecution, is Gobbo."
Ms Gobbo was not just a go-to barrister for Melbourne's criminal underworld, she was also a registered Victoria Police informer for more than a decade.
It was she who provided details to Victoria Police - later passed on to the Australian Federal Police and Australian Customs - about the tomato tins import.
Mr Grace said it's yet to be tested whether Higgs' prosecution for the tomato tins conspiracy was compromised in any adverse way by the nature of Ms Gobbo's relationship with him and Victoria Police.
But there was sufficient evidence to indicate the advice given to Higgs by Ms Gobbo during the trial was compromised by her lack of independence, he said.
He also argued there were exceptional circumstances pointing to grounds for Higgs' release while his appeal is pending, pointing to the fact he has served almost two thirds of the total non-parole period, plus his age and health.
Higgs has already spent nine years in custody for the offending after he was convicted by a jury in 2012.
"If his appeal is successful and Your Honours do not grant bail today, he may well have spent all this time for nothing," Mr Grace said.
Prosecutors opposed the bail application. A decision is expected to be handed down on Monday.
Australian Associated Press