Dripping in jewellery and a silk Versace shirt was Mafia figure Pasquale Barbaro, seated at a table inside Rockpool Bar and Grill with his girlfriend.

At a nearby table was a group of mates from the city's south-west, some of whom still bared the tattoos symbolising their allegiance to the Brothers for Life gang.

Barbaro had long-running tensions with some members of the now-defunct street gang. That animosity stemmed from a fight with Mohammed Hamzy, the now jailed leader of the Brothers for Life Bankstown chapter.

Hamzy – known as "Little crazy" or "LC" – and Barbaro had a punch-up in jail in 2012 but it was LC that apparently came out victorious.

Sources say this didn't stop Barbaro mouthing off about Hamzy when he was later released.

When Hamzy got wind of this, Barbaro was forced to pay the Brothers for Life figure $300,000 to smooth things over. It was a practice Barbaro – who had a reputation for using his illicitly-earned cash to settle conflicts – was used to.

However, when Hamzy's older brother Khaled walked into Rockpool on Hunter Street that Saturday night in July, the animosity was still there.

An eyewitness  says a heated exchange took place after Khaled confronted Barbaro, a loyal Rockpool customer, in the upmarket dining room, and the confrontation threatened to turn physical.

It is an example of the many conflicts Barbaro found himself in, in varying underworld circles, before his execution this week.

"There are many people that would have wanted to knock him for what Pasquale did to them," one source says.

Barbaro has been painted as a man with countless enemies who was happy to mouth off about his associates but shied away from conflict.

"He always had bodyguards because if there was dramas he would never sort it out himself," one insider says. "He was a weakling."

But three weeks ago everyone, including his bodyguard, appeared to desert Barbaro.

On Monday night, as he left the Earlwood home of construction industry figure George Alex, at least one gunman with two accomplices jumped out of an Audi four-wheel-drive and opened fire. Witnesses heard seven shots before finding the tattooed, heavyset father-of-two dead on the footpath.

Barbaro was the eighth underworld figure executed in Sydney in the last 18 months.

Family ties

In some ways Barbaro never had a chance. Decent male role models in his family have been in short supply.

Father Guiseppe "Joe" had already served two stints behind bars for drug offences and was on the run trying to avoid a third stint when Barbaro's half-sister baby Montana was kidnapped in Melbourne 2004.

Pasquale Barbaro's father Joe Barbaro. Photo: Paul Harris

All hell broke loose in Joe's private life when it emerged he had eight children with three women.

The existence of his other family in Melbourne was news to his fiancee Tanya Flynn, a Canberra dancer, who had two children with Joe. Waving her unworn wedding dress before the cameras, Flynn announced the wedding was off.

But Montana's mother, Anita Ciancio, 20 years his junior, was not concerned by her partner's secret life later saying of Joe: "Just because he is older and uglier than me does not mean he is not worth my love."

Not long after the kidnapping Joe was extradited to NSW. In 2002 he organised for his son, Barbaro, to supply him with 1000 methylamphetamine tablets.

Both father and son were jailed over this. Joe later appealed, unsuccessfully, claiming that the sentencing judge had given insufficient weight to the effect of the kidnapping.

That same year, 2006, also saw Joe's brother "Fat" Frank jailed for four years over his own ecstasy bust.

Barbaro was only 25 when he and his father were jailed but he already had an extensive rap sheet, including a stint in jail in the ACT over the armed robbery of the Helenic Club during which a security guard was bashed with a steel pipe.

Once out of jail for the drug offences committed with his father, Barbaro was back in the family business – drug manufacturing.

Pasquale Barbaro was shot dead in Earlwood on Monday. Photo: Instagram

This time, in July 2012, Barbaro and his younger brother Rossario were arrested and charged with manufacturing two kilograms of the drug ice.

While on bail Rossario was arrested in Queensland in 2014 over 36 kilograms of ice that police allegedly found in his car. His attempt to get bail last year failed after the police raised his "appalling criminal history", which included 30 convictions.

Pasquale's grandfather, also called Pasquale Barbaro, was involved in the drug world. He was murdered in Brisbane in 1990, having survived a previous attempt on his life. His brothers Antonio and Francesco (also known as "Little Trees") were senior mafia figures based in Griffith and were named in the Woodward Royal Commission into Drug Trafficking.

Franceso's son, also called Pasquale, is currently in jail over the world's largest ecstasy bust.

A complex web

At the time he was shot dead at Earlwood, Barbaro was on $350,000 bail for the 2012 drugs charges and was due to face trial early next year.

The execution-style hit transpired the night before a Sydney court was played phone intercepts of him speaking to his close friend, Brothers For Life gang leader Farhad Qaumi.

Despite being a member of the same street gang, Qaumi – known as "the Afghan" – had also been in a long-running, deadly feud with the Hamzy family Barbaro had brawled with at Rockpool.

The phone intercepts of Barbaro were played as part of the evidence against Qaumi, who is on trial for allegedly arranging the murder of standover man Joe Antoun at Strathfield in 2013.

In what demonstrates the complex and delicate nature of Sydney's underworld, Antoun was business partners and a close associate of Alex – the man Barbaro had been visiting when he was gunned down.

George Alex.  

Barbaro also claimed that he twice attempted to kill Antoun over an outstanding drug debt but had aborted the hit on both occasions because the standover man's wife and had answered the door. At the time Antoun was shot dead, Barbaro was pursuing him over an alleged $750,000 debt owed to Griffith wine merchants.

In this complex web of Sydney's underworld, Barbaro  found himself squarely in the middle.

"He had the name, the Barbaro name, and people wanted to do business with him because of that," one insider says. "But he was cocky and he'd screw people over. No one could trust him."

He had Mafia ties, he was close with Afghan gangsters like Qaumi, he was known to be hanging around with senior Hells Angels bikies and partied with Kings Cross identities including Michael Ibrahim.

Others described him as a bully and a thug. "He's got 100 people that want to knock him," another well-known crime figure says.

It was widely rumoured that Barbaro was a "snitch" or a law enforcement informant, although it was a claim he denied.

He had survived at least two previous shootings.

The first was on New Year's Day 2014 when three gunman opened fire on a luxury Oscar II yacht that Barbaro was on, partying with other gangsters including Qaumi and Kings Cross identity Adam Freeman, son of bookie and organised crime figure George Freeman.

Qaumi was struck in the shoulder in what police believe was an attack aimed at killing him. Barbaro was unhurt.

Then in November 2015, Barbaro survived an attempt on his life at Leichhardt, in Sydney's inner-west. He was shot at several times but miraculously escaped injury.

That shooting, almost a year to the day before he was killed, was believed to have been carried out by another underworld figure, Hamad Assaad.

Hamad Assaad was shot dead on October 25. Photo: Instagram

Assaad and Barbaro were close associates of Dallas Fitzgerald, the national sergeant-at-arms of the Hells Angels and son of one of the club's most senior figures, Felix Lyle. Assaad was shot dead in front of a 12-year-old relative as he left his Georges Hall home on October 25.

The 29-year-old was a prime suspect in the shooting of Walid "Wally" Ahmad in April, a brazen murder at Bankstown shopping centre that Assaad, who was known by the street name "H", had been bragging about.

The deaths of Barbaro, Assaad, Ahmad and five other fatal underworld shootings in the last 18 months has prompted police on Thursday to establish a specialist strike force, Osprey, to look for links between them and to stop any further bloodshed.

It is a similar tactic used by Victorian Police at the height of the Melbourne gangland killings that involved that city's biggest underworld figures and was immortalised in the television series Underbelly.

Melbourne's gangland war stretched 12 years and ended with 36 bodies. NSW Police will be hoping the tally remains at eight.