The fall of criminal Michael Ibrahim
When the youngest member of the notorious Ibrahim crime family was serving time for manslaughter, he vowed to turn his life around so he could take care of his mother.
Being behind bars while his mum Wahiba had cancer was a "wake-up call", Michael Ibrahim told the NSW parole board in 2013.
But now the ailing Ibrahim matriarch will likely never see her son as a free man, after he was this week sentenced to 30 years in prison for his role in a global drug ring involving Sydney's underworld heavyweights.
The favourite brother of Kings Cross identity John Ibrahim was duped by an undercover cop as they teamed up to bring narcotics worth $810 million into Australia.
Ibrahim boasted he'd get rich importing nearly two tonnes of MDMA, 136 kilograms of cocaine and 15kg of ice from Europe in 2017, unaware he was the centrepiece of an 18-month police investigation.
After spending much of his adult life locked up, the 42-year-old was handed a non-parole period of 18 years on Wednesday.
"If not already institutionalised, he will certainly be so by the time he is released," Judge Dina Yehia told Downing Centre District Court.
'WE'RE GONNA MAKE MILLIONS'
The convicted killer claimed to be the victim of entrapment from the officer who encouraged him to "go bigger" in the operation which spanned Australia, the Middle East and Europe.
The fake smuggler was welcomed into the Ibrahim inner circle by Michael who considered him "a brother", after he convinced the seasoned criminal he could make drugs and cigarettes slip past border officials.
But Judge Yehia said Ibrahim embraced the lucrative opportunity and "was not a reluctant or unwilling participant… or naive''.
At one stage Ibrahim flew to the Netherlands to sample the drugs, and ran money-laundering operations with black market tobacco imports.
"We're gonna make millions, f***ing million a week, we're talking about tens of millions, even making hundreds of millions of dollars," Ibrahim told the undercover operative, unable to contain his excitement.
"F***ing 50 million dollars each."
Ibrahim stood to gain a large cut of the profits by wielding his power to ensure two dangerous factions within the syndicate wouldn't cheat each other.
Judge Yehia said while Ibrahim was not the linchpin of the Sydney group, "his role extended beyond merely making introductions''.
"The offender was a trusted and respected participant in the enterprise… expecting significant financial gain," she said.
Ibrahim assured suspicious accomplices that he trusted the undercover cop "100 per cent" and even offered to be his right-hand man, telling the officer: "No one's going to rip me off."
The court heard that when Ibrahim found out two partners had skimmed $65,000 from his bootleg tobacco fund, he shaved strips down the middle of their heads and sent photos of their new haircuts to his associates.
His brother John also famously ordered eyebrow waxings as punishment for Jaron Chester and former real estate agent Ryan Watsford, the two underlings who'd allegedly been caught stealing.
It was Watsford who first introduced the undercover operative to Michael at a luxury Sydney hotel in 2016.
"Mate listen, I've got f***ing 50 litres and 50 kegs of coke in Lebanon," he told the cop, who wore a wire.
The syndicate was brought down in August 2017 when Ibrahim was nabbed in Dubai along with Sydney drug lord Mostafa Dib, who were among more than 20 Australians charged. The arrests triggered more than 500 police officers raiding 30 homes across Sydney, including Ibrahim's businessman brother John's eastern suburbs mansion.
John has not been charged and there is no suggestion he committed any crime.
More than $5.4 million was seized and six Dutch nationals were also arrested, while the massive haul of drugs bound for Australia was intercepted by authorities in the Netherlands.
After being extradited to Sydney, Michael Ibrahim stared down the barrel of the mugshot camera at Surry Hills police station in September 2017.
His drug empire was in tatters and he was facing life behind bars but, living up to his cheeky nature, Ibrahim cracked a toothy grin.
The following year Ibrahim, whose birth name is Moustafa and nicknames are Mick, Mario and ''Errand Boy'', pleaded guilty to a string of commercial drug importation and money-laundering charges.
Judge Yehia said Ibrahim's ''letter of apology'' to the court "does not contain an apology or any expression of remorse''.
Instead, he grumbles about being held in segregation inside multiple NSW prisons, saying it affected his mental health.
"I was locked into my cell for about 23 hours a day," Ibrahim wrote.
"I was always stressed, worried, upset and depressed. I was losing my mind in segregation and I complained over and over again."
Ibrahim goes on to claim he was bashed by cops in the United Arab Emirates.
"I was beaten, tasered and forced to sign a document in Arabic," he wrote.
Dib was also tortured by Dubai police, for which he got some time knocked off his maximum 18-year sentence earlier this month.
The brother of murdered crime kingpin Wally Ahmad, Ahmad "Rock" Ahmad, and bikie boss Hassan Fakhreddine also await sentencing for their roles in the smuggling plot.
Last year Watsford was handed at least four years' imprisonment after pleading guilty to attempted commercial drug importation and dealing in proceeds of crime.
The ex-Cranbrook student's lawyers said he was under the control of Ibrahim during the planning phase for the imports, when the undercover cop first said: "If you want results, you take risks."
Judge Yehia said Ibrahim was happy sneaking nearly 1.4 million packets of untaxed cigarettes into the country using the operative's connections from 2016, but soon became conflicted about "an ever-increasing quantity of drugs''.
"I don't want nothing to do with the drugs… this is all a favour to you, to get you going," Ibrahim told the officer.
At one point Ibrahim backed out of the operation altogether and arranged for Watsford to take his commission, the court heard.
However that change of heart did not last long, and Ibrahim soon apologised to the undercover cop, saying he "just freaked out for a moment''.
Ibrahim received a 25 per cent sentence discount for his early guilty plea but Judge Yehia said "he is not entitled to the leniency that would be afforded to a first-time offender''.
IN HIS BLOOD
Ibrahim's long criminal history includes the manslaughter of Robin Nassour, the brother of Fat Pizza TV comedian George Nassour, who he stabbed with his cousins Mouhamed and Sleiman Tajjour in 2006.
At his 2008 sentencing, the court heard Ibrahim had a close bond with his mum, and he's been exceptionally protective of her since his father left home for Lebanon to take a second wife. Wahiba came to Australia in 1972 as a refugee, and her gambling-addicted husband was often absent, leaving her to raise six children alone, the court heard.
In 2008 Ibrahim said he wanted to rehabilitate and get a job to take care of his mum, while the court heard "his incarceration has served as a source of immense distress for each of them''.
Judge Yehia said Ibrahim struggled at school where he was bullied and also suffered "beatings from his older brothers''.
But she stressed Ibrahim's low intelligence didn't excuse his crimes.
The court also heard Ibrahim's wife has remained by his side, but that he started abusing MDMA and cannabis after she had a miscarriage.
Caitlan Hall wrote to the court about her "anguish" after her husband was shot during an attack outside his Sydney city home in 2015, which worsened his increasing paranoia.
The former nightclub doorman was returning to his multimillion-dollar rental apartment on Macquarie Street at night when two men wearing balaclavas jumped out of a white Audi and opened fire.
Despite being hit in the shoulder Ibrahim took a taxi to hospital for surgery, becoming just the latest member of his family to be targeted.
John was knifed in 1986 after breaking up a Kings Cross fight, former Nomads bikie boss Sam was hit in a 2011 drive-by shooting and even Wahiba's house was sprayed with bullets while she was recovering from breast cancer surgery.
The 72-year-old mum's heartache isn't over, with Sam facing deportation to Lebanon once her son's minimum six-year jail term expires for his role in a gun racket with former rock'n'roll drummer Paul DeMarco.
Wahiba is now too sick to visit Michael in prison, which Judge Yehia said "will weigh heavily on the offender during his time in custody''.
"There is a real chance that his mother will never see her son as a free man," she said. Michael Ibrahim will be eligible for parole in 2035.
Originally published as The fall of Michael Ibrahim: What brought him unstuck