Two of their sons died in gangland shootouts, two others face drug trafficking or murder charges in mob-related cases, and a fifth is on the run abroad. Now, their parents are learning another hard lesson in breeding a self-made crime group — they’ve lost the $170,000 they posted to have their eldest son released from jail.

Hossein Al Khalil and Soumayya Azzam were fighting in court to salvage bond money paid to have Nabil Alkhalil released.

Their bond was lost when he fled Canada on a bogus passport soon after his release.

The judge’s ruling against them — with Nabil still a fugitive — is but one entry in an unrelenting stream of bad news involving their sons.

“These two parents of five sons came to Canada, presumably to make a better life for themselves. Now, having buried two kids before they reached the age of 20, they have two more facing the possibility of a long time in prison,” said Sgt. Lindsey Houghton of B.C.’s Combined Forces Special Enforcement Unit. “The actions of these boys have destroyed that family.”

The family arrived in Canada from Saudi Arabia as refugees in 1990, although their roots are believed to be in Iran, and settled in Surrey.

After two sons were killed in gangland violence, they moved to Ottawa, then Montreal.

“They took all of their organized crime and gang connections with them,” said Houghton.

The couple’s second son had been the first to die.

In 2001, Khalil Alkhalil, 19, was shot dead in Surrey in a gunfight over a drug debt. His killer claimed self-defence and was freed. The shooter’s lawyer was beaten up in court by angry supporters of Alkhalil, and the shooter himself was later gunned down in Kelowna in a case that remains unsolved.

The fourth son, Mahmoud Alkhalil, was one of three people killed in a notorious gunfight in 2003 between gang rivals in Vancouver’s Loft Six nightclub. He made it out of the building, but was found bleeding and unconscious after crashing his car 20 blocks away. When he succumbed to his injuries at age 19, he already had a lengthy criminal record.

The youngest son, Rabih “Robby” Alkhalil, was only two when he came to Canada.

In February, Rabih was extradited to Canada after his arrest in Greece; Crown attorneys in three provinces are now lining up to see who gets first crack at prosecuting him.

In Vancouver, he is charged with first-degree murder in the 2012 hit on gangster Sandip “Dip” Duhre in the Sheraton Wall Centre. In Toronto, he is charged with first-degree murder in the 2012 shooting of Johnnie Raposo on the patio of the Sicilian Sidewalk Cafe in Little Italy. In Montreal and in Niagara Falls, Ont., he faces cocaine smuggling charges with a member of the Hells Angels.

The couple’s third son, Hisham “Terry” Alkhalil, was arrested last year in Ottawa in what officers called “a pre-emptive strike” to avert a gang war. Police seized 24.5 kilograms of cocaine with an estimated street value of $12.5 million, four guns and an opulent $1.2 million home Hisham was about to move into.

Nabil is the eldest. Soon after his release from jail in 2005 for assault, his Cadillac was stopped for speeding on Highway 401 near Cornwall, Ont.

When Nabil, the driver, was asked to open the trunk, he drove off, leaving his brother Hisham behind as he led police on a long, high-speed chase. When he was caught, a duffel bag with 11 kilos of cocaine was found nearby.

Nabil was convicted of cocaine trafficking and ordered deported, as he had been before. But because he is considered stateless — no country will grant him travel papers as a citizen — he is considered unremovable.

He was released from immigration detention in 2010 after his parents posted $170,000 as surety.

Nabil’s wife, Louisa, told court her husband wanted to leave Canada because rival gangs were targeting him and his family.

She said Ottawa police warned him of threats against his life and he caught a private investigator watching their home. He feared rivals planned to kill him as retaliation against his brother Rabih.

He once visited the Lebanese embassy to obtain a passport but was unsuccessful, she said.

On Nov. 3, 2013, Nabil left home and called her three days later saying he was “somewhere in the Middle East,” she said. He is willing to meet Canadian officials abroad so they can confirm his departure, but no such arrangements have been made, court heard.

It was a violation of many of his strict conditions, including curfew and residences requirements. Canada Border Services Agency wrote to Nabil’s parents, saying their bond had been forfeited and demanding cheques to cover the remainder of the surety.

The parents complained to the Federal Court of Canada. Judge Richard Mosley found they were “not wholly without guilt” in Nabil’s flight because they waited three days before alerting border services.

Police who have investigated the family for years said they are a stark example of the damage and danger that can come with a life of crime.

“These three brothers, despite what tragedy their family has undergone, have evolved their criminal activities and taken them to highest levels on an international scale,” said Houghton.

“They built a family crime group empire.”

But to do so they have lost so much.

A call to the parents’ Toronto lawyer was not returned before deadline on Thursday.

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