It started with a plane touching down on Canadian soil—another family of refugees escaping war, seeking a fresh start. But within a generation, the Alkhalil name would be whispered in fear across Canada’s criminal underworld.
The five brothers—Nabil, Mahmoud, Hisham, Mahmoud and Rabih—didn’t just dip into crime; they built an empire of drug smuggling, gangland executions, and high-stakes betrayals, stretching from Vancouver’s back alleys to Mexico’s cartel strongholds.
All five brothers were born in Saudi Arabia to Palestinian refugee parents before immigrating to Canada in 1990 as refugees.
The five brothers included:
Nabil Alkhalil (1976–2018)
Khalil Alkhalil (1981–2001)
Hisham "Terry" Alkhalil (born 1982)
Mahmoud Alkhalil (1984–2003)
Rabih "Robby" Alkhalil (born 8 May 1987)
The craziest part of their tale? Rabih Alkhalil, wasn’t just Canada’s most wanted fugitive—he had pulled off a Hollywood-style prison escape, walking out of a maximum-security facility dressed as a construction worker, vanishing without a trace.
This is the real story behind the Alkhalil crime family.
The Murder of Khalil Alkhalil: The First Shot
A Violent Reputation at 19
By the time 19-year-old Khalil Alkhalil was found dead on January 18, 2001, his body riddled with six bullets, his name was already well known to law enforcement.
Despite his young age, Khalil had built a reputation for violence and intimidation, accumulating convictions for assault, weapons possession, uttering death threats, and obstruction of police.
His killer, 20-year-old Martin Naud, was an automobile mechanic's apprentice and a low-level drug dealer. According to Naud, Khalil had attempted to rob him at gunpoint, demanding $200 worth of drugs.
In the struggle, Naud wrestled the gun away from Khalil and fired six shots at close range, hitting him multiple times in the chest and abdomen.
Khalil collapsed in the entranceway of a Surrey apartment complex, bleeding out before paramedics arrived. The execution-style nature of the killing immediately raised suspicions, leading to Naud’s arrest and charge for second-degree murder.
A Courtroom Showdown
The violence didn’t end with Khalil’s murder. Just over two weeks later, on February 3, 2001, when Naud was granted bail, the Alkhalil family descended upon the courtroom in New Westminster, ready to send a message.
Around 30 of them, including Khalil’s brothers Mahmoud and Nabil, filled the room, glowering at Naud’s family and legal team.
When Naud’s female friend walked by, one of the Alkhalil women snapped, “You scared, bitch? You better be!” The tension escalated when Naud’s release was confirmed—the Alkhalil family erupted in rage, cursing at the judge and Crown Attorney.
But their final display was the most chilling. As Naud left the courtroom, the Alkhalils began to chant in Arabic:
“Khalil’s not dead!”
“One Alkhalil is gone, but there are still hundreds of us! You will have to face us all!”
The courthouse, which had seen its share of gang-related cases, had never witnessed such an open display of hostility and vengeance.
Things turned physical when Naud’s lawyer, Philip Rankin, tried to leave the courtroom.
Mahmoud Alkhalil suddenly lunged at him, punching him in the face so hard that one of Rankin’s teeth broke on impact. The attack wasn’t just about anger—it was a deliberate message that anyone standing with Naud was an enemy.
Terrorizing the Naud Family
What followed was months of relentless intimidation. The Naud family home was targeted at least three times—gunshots were fired into their house, shattering windows and embedding bullets in the walls. One night, a machete was left embedded in their front lawn, a silent but unmistakable death threat.
Anonymous leaflets began circulating in their neighborhood, branding Naud a murderer and encouraging vigilante justice. The harassment became unbearable, forcing Naud’s mother to flee BC. She left behind everything, terrified that staying would mean a death sentence for her or her son.
Naud’s lawyer, Philip Rankin, wasn’t spared either. Over the following months, Mahmoud Alkhalil tracked him down and assaulted him on multiple occasions—punching him in the stomach in one instance, and ambushing him outside his office in another.
Rankin, a seasoned lawyer, had dealt with criminals before, but never had he been physically attacked by the family of an accused person.
A Trial That Ended in Acquittal
When Naud’s murder trial began in 2002, it became clear how deep the feud between the Alkhalil family and their enemies had already become. At trial, Naud testified that Khalil had tried to rob him and that he only shot in self-defense.
The evidence supported his claim—Naud himself had been shot in the hand during the struggle, and forensic experts determined that Khalil had gunpowder residue on his fingers, proving he had fired first.
On November 7, 2002, the jury ruled in Naud’s favor—acquitting him of all charges on the grounds of self-defense. For Naud, however, this was not the end.
The Execution of Martin Naud
On April 11, 2003, less than five months after the trial, Naud’s father, Raymond Naud, was shot and wounded inside his own house. Though he survived, it was clear the attacks on the Naud family had not stopped.
Then, on July 5, 2004, Martin Naud himself was executed in Kelowna. As he was getting out of his car, an unknown gunman approached and fired multiple shots. Naud was hit in the chest and head, killing him instantly.
Police strongly suspected that the Alkhalil family had ordered the hit, but no one was ever arrested for the killing.
The murder of Khalil Alkhalil in 2001 had set off a chain reaction of bloodshed that continued for decades, fueling a long-standing gang war between the Alkhalils and the Dhak-Duhre group.
The Dhak-Duhre Gang
Naud was working as a low-level drug dealer with ties to the Dhak-Duhre group, a criminal organization that was deeply entrenched in British Columbia's drug trade.
The Dhak-Duhre group, led by the Dhak brothers (Sukhvir and Gurmit Dhak) and the Duhre brothers (Balraj, Sandip, and Paul Duhre), was known for its violent turf wars with rival gangs, including the Hells Angels and Red Scorpions.
They were a dominant force in Metro Vancouver's underworld, controlling significant portions of the drug trafficking and enforcement operations in the region.
Despite Naud’s relatively minor role in the organization, the Alkhalil family believed that the Duhres were responsible for Khalil's death, or at the very least, had helped Naud.
This perception fueled a long-standing feud between the Alkhalils and the Dhak-Duhre group. Over the next 20+ years, the conflict intensified with multiple high-profile murders, shaping the landscape of organized crime in BC.
Murder of Mahmoud Alkhalil: A Nightclub Shootout with the Hells Angels
On August 16, 2003, Mahmoud Alkhalil, a 19-year-old member of the Independent Soldiers street gang, was shot and killed in a violent shootout inside Loft Six, a well-known nightclub in Gastown, Vancouver.
On the night of August 16, 2003, Loft Six was packed with clubgoers—including Sandip “Dip” Duhre, a known figure in the Dhak-Duhre gang, who was also present at the club.
According to witnesses, gunfire suddenly erupted on the dance floor. The Hells Angels had entered Loft Six and a confrontation escalated into a shootout. Mahmoud, who was armed, reportedly fired back at his attackers as bullets tore through the packed venue, sending panicked patrons diving for cover.
Despite his efforts to fight back, Mahmoud was struck multiple times. Severely wounded but still conscious, he managed to escape the nightclub, staggering to his car parked a few blocks away.
He attempted to drive himself to safety but succumbed to massive blood loss, his car coming to a stop just a short distance from the club.
Paramedics arrived shortly after, but he was pronounced dead at the scene.
Blame, Retaliation & Alkhalil-Duhre Feud
Though it was the Hells Angels who had been directly involved in Mahmoud’s death, the Alkhalil family placed the blame on Sandip “Dip” Duhre.
Whether or not Duhre had a role in instigating the violence remains unclear, but the perception among the Alkhalils was that he had either set Mahmoud up or played some role in provoking the attack.
This belief intensified the already volatile feud between the Alkhalils and the Dhak-Duhre group, fueling years of retaliatory violence. While Mahmoud's murder may have been an unintended consequence of a dispute involving multiple factions, it further cemented the Alkhalil family's determination for revenge.
To this day, no arrests have been made in connection with Mahmoud’s murder, and his killing remains an unsolved chapter.
The Rise and Fall of Nabil Alkhalil: High-Speed Chases, Drug Trafficking, and a Fatal Money Dispute
Following the violent deaths of his younger brothers Khalil and Mahmoud, Nabil Alkhalil moved to Ottawa, where he remained deeply entrenched in organized crime.
By the mid-2000s, his activities had already placed him on law enforcement’s radar, but it was an audacious high-speed chase in 2005 that truly cemented his notoriety.
On May 1, 2005, Nabil was driving his white Cadillac Deville along a highway in eastern Ontario when he was spotted by police. Rather than pulling over, he initiated a high-speed chase, reaching speeds of more than 210 km/h over a 32-kilometer stretch of highway and backroads.
The pursuit ended outside Cornwall, where Nabil abandoned his vehicle and attempted to flee on foot. However, he was quickly captured.
Upon searching the car, police found a duffel bag containing 11 kilograms of cocaine—a massive haul that confirmed Nabil’s status as a major player in the Canadian drug trade.
At his trial, Justice Hugh McLean remarked on Nabil’s extensive criminal history, noting that he was already under a deportation order to be sent back to Saudi Arabia due to his record. Instead of immediate deportation, however, Nabil was sentenced to prison for:
✅ Possession of narcotics with intent to traffic
✅ Dangerous driving
✅ Failing to stop for police
Attempts to Evade Deportation
Despite the standing deportation order, Nabil remained in Canada following his release from prison. He made multiple visits to the Lebanese embassy in Ottawa, attempting—unsuccessfully—to obtain a Lebanese passport. These failed efforts left him stateless, as neither Canada nor Saudi Arabia was willing to claim him.
By November 2010, Nabil had vanished from Canada after receiving warnings that rival gangsters wanted him dead. His parents, Hossein Alkhalil and Soumayya Azzam, lost $170,000 in bail money, which they had posted for their son.
A Global Fugitive: Mexico, Colombia, and the Sinaloa Cartel
Nabil’s next known location was Mexico in 2013, where he entered the country using a forged Canadian passport. While in Ciudad López Mateos, he worked at a used car dealership—likely as a front for his continued criminal activities.
Intelligence reports later suggested that
Nabil served as the Alkhalil family’s liaison with the Sinaloa Cartel, facilitating drug shipments between Mexico and Canada.
His movements remained shadowy and unpredictable, and in November 2013, Nabil called his mother in Surrey, British Columbia, cryptically telling her that he was "somewhere in the Middle East." This would prove to be a diversion, as records indicate that by 2015, he had been arrested in Colombia.
Arrest in Colombia & Another Escape
Nabil’s downfall seemed imminent when airport officials in Bogotá, Colombia, discovered that he was traveling under a forged Canadian passport. He was immediately detained, but instead of facing extradition or prosecution, he was sent to Panama City—where he vanished once again.
The Money Dispute That Ended It All
On August 24, 2018, Nabil’s luck ran out. He was in Ciudad López Mateos, where he got into a heated dispute with a wealthy businessman, Javier Armando Nuñez.
The argument—reportedly over money—became increasingly hostile, with both men shouting. The confrontation ended abruptly when Nabil was shot dead with a 9mm handgun.
The State of Mexico police later arrested José Mario Venegas González, Nuñez’s bodyguard, and charged him with the murder. However, Nabil’s parents publicly disputed the case, claiming that:
🔹 Venegas was merely a fall guy
🔹 No gunpowder residue was found on Venegas’s hands
🔹 The police never inspected Nuñez for gunpowder residue
Despite these claims, the Mexican authorities closed the case, and Nabil’s death marked the third Alkhalil brother to meet a violent end.
Hisham "Terry" Alkhalil: The Ottawa Connection
Hisham "Terry" Alkhalil was one of the less publicized members of the Alkhalil family, but his role in organized crime was no less significant. Unlike his brothers, who were known for their direct involvement in violent conflicts and high-profile murders, Hisham operated behind the scenes, focusing on large-scale drug trafficking.
His base of operations was Ottawa, where he controlled lucrative cocaine distribution networks that extended across the country.
Project Anarchy and Hisham’s Arrest
On January 30, 2014, as part of Project Anarchy, a massive drug investigation, Hisham was arrested in Ottawa and charged with conspiracy to traffic cocaine.
The police seized a staggering 54 pounds of cocaine, with a street value of approximately $12 million. In addition, authorities confiscated his lavish $1.1 million home on Rossland Avenue, labeling it as proceeds of crime.
Hisham had also been the owner of the Abu Abed Café, a business suspected to be a money laundering front. On January 14, 2016, Ottawa police seized the café, citing its deep connections to criminal activities.
The café had long been under scrutiny, with law enforcement suspecting it was being used for meetings between members of Ottawa’s criminal underworld.
Police Concern Over Violence in Ottawa
Authorities believed that Hisham's connections to international drug suppliers and his family’s long-standing gang feuds could lead to retaliatory violence in the city.
Mike Laviolette of the Ottawa police, who played a key role in Project Anarchy, stated:
"They were very active, not just on a local and national level, but an international level as well, which demonstrated their ability to just be as mobile as they wanted to be... It was the propensity for violence — the potential for them being violent, or people who wanted them dead being violent, in our city. We disrupted them enough that we were able to prevent any type of large-scale violence within our city."
The Charges Are Dropped
Despite the overwhelming evidence against Hisham, his case never went to trial. In 2018, a judge ruled that the Crown had taken too long to bring the case forward, and the charges were stayed, allowing Hisham to walk free.
This decision frustrated law enforcement, as the police had invested years in investigating the Alkhalil family's criminal operations, only for one of their key members to evade justice due to legal technicalities.
Hisham’s current whereabouts and criminal involvement remain unknown, but his ability to avoid conviction highlights the complexity of dismantling the Alkhalil family's operations, which stretched beyond borders and involved some of the most dangerous criminal organizations in North America.
Rabih Alkhalil: The Mastermind of the Wolfpack Alliance
Establishing Power in Montreal
Rabih "Robby" Alkhalil relocated to Montreal, where he built a high-profile criminal empire. Alkhalil was a key leader of the Wolfpack Alliance, an inter-gang coalition that included members from:
Hells Angels (Amero’s faction)
Independent Soldiers
Red Scorpions
West End Gang (led by Shane Maloney)
He lived in a luxury penthouse condo at 555 René Lévesque Boulevard West, boasting a panoramic view of the St. Lawrence River.
Montreal is a critical hub for organized crime, serving as Canada’s main gateway for drug smuggling due to its major port access, highway connections to the U.S., and proximity to New York City—North America’s wealthiest drug market.
Since the days of Prohibition, Montreal had been a key smuggling route to the U.S., and Alkhalil saw it as the perfect base for expansion.
He partnered with Hells Angels kingpin Larry Amero, and together, they used it as a stepping stone to infiltrate New York’s cocaine trade.
The Wolfpack Alliance & the Sinaloa Cartel Connection
The Wolfpack operated as a distribution arm for Mexico’s Sinaloa Cartel, led by Joaquín "El Chapo" Guzmán. Hundreds of kilograms of cocaine flowed monthly from Mexico to Canada under their control, often hidden inside secret compartments in transport trucks.
To manage his expanding operations, Alkhalil relied heavily on encrypted communication, using the Pretty Good Privacy (PGP) system to coordinate drug shipments and contract killings.
He even owned a high-end fashion boutique in Old Montreal, a front business for laundering drug profits. His penthouse doubled as a criminal headquarters, where he hosted meetings with cartel representatives and elite gangsters.
The Murder of Sandip "Dip" Duhre (2012)
On January 17, 2012, Sandip "Dip" Duhre, co-leader of the Dhak-Duhre Group, was executed inside Vancouver’s Sheraton Wall Centre.
Hitman Dean Michael Wiwchar, a known enforcer for the Wolfpack, was charged with carrying out the assassination on behalf of Rabih "Robby" Alkhalil.
Security footage showed a masked gunman calmly walking into the hotel’s lobby before firing multiple shots at Duhre at point-blank range.
The brutal execution was widely seen as retaliation for the murder of Jonathan Bacon (a Wolfpack ally) in 2011.
This escalated the gang war between the Wolfpack Alliance and the Dhak-Duhre Group, triggering a series of retaliatory murders across Canada.
Plotting the Sicilian Sidewalk Café Execution (2012)
In spring 2012, Rabih Alkhalil was involved in a multi-million-dollar cocaine deal with fellow Wolfpack members:
Nick Nero (Ontario-based trafficker)
Martino "Lil Guy" Caputo
Johnny Raposo (Toronto drug dealer)
The 200-kilogram shipment was supposed to be split evenly, but Alkhalil, Nero, and Caputo decided to kill Raposo to take his share.
On May 21, 2012, Alkhalil texted hitman Wiwchar, ordering him to assassinate Raposo for $100,000.
On June 18, 2012, as Raposo sat on the patio of Toronto’s Sicilian Sidewalk Café, watching a Euro Cup match, Wiwchar approached disguised as a construction worker, wearing a dust mask and blonde wig.
Without hesitation, he shot Raposo in the back of the head multiple times before escaping.
Four days later, Wiwchar was arrested in Toronto. When told he was being charged with first-degree murder, he mockingly asked the arresting officer, "Which one?"
The Fall of the Wolfpack
On August 8, 2012, Montreal police raided Rabih Alkhalil’s luxury condo with arrest warrants for both Alkhalil and Amero—but both had already fled.
In November 2012, Alkhalil was charged in absentia with drug trafficking as part of Project Loquace, a major Quebec anti-drug operation.
By February 23, 2013, authorities finally caught up to him. He was arrested in Greece, living under a forged French passport while posing as a haute couture designer.
Convictions for Drug Trafficking and Murder
Trial for Johnny Raposo’s Murder (2017)
In April 2017, Alkhalil stood trial in Toronto for the first-degree murder of Johnny Raposo. The Crown’s case relied on 41,420 encrypted messages exchanged between Alkhalil, Nero, Caputo, and Wiwchar over three months.
Alkhalil pleaded not guilty but refused to testify, likely to avoid difficult cross-examination about his texts.
On May 11, 2017, he was convicted of first-degree murder, along with Nero, Caputo, and Wiwchar.
Montreal Drug Trafficking Charges (2020)
On August 21, 2020, after a separate trial, he was convicted of conspiracy to traffic cocaine and sentenced to eight years in prison.
Vancouver Trial for Duhre and Dhak Murders (2021-2022)
In 2021, Alkhalil and Amero were put on trial for the murders of Sandip Duhre and Sukh Dhak. The Crown alleged that Alkhalil and Amero had ordered the hits to wipe out the Dhak-Duhre Group.
But before the trial concluded, Alkhalil pulled off one of the most shocking prison escapes in Canadian history.
The Daring 2022 Prison Escape
On July 21, 2022, Alkhalil escaped from North Fraser Pretrial Centre, a maximum-security facility.
How It Happened:
Two men disguised as construction workers arrived with a plasma torch.
They cut through the jail’s perimeter fence.
Alkhalil, dressed in a construction vest, walked out undetected.
They fled in a white van, which was later found abandoned.
By the time authorities realized what had happened, he had vanished.
On August 12, 2022, he was charged with:
Forcible prison break
Escaping lawful custody
The Aftermath: Canada’s Most Wanted Fugitive
On 29 August 2022, Larry Amero was convicted of two counts of conspiracy to commit murder in connection with the slayings of Sandip Duhre and Suhhveer Dhak.
And Alkhalil was also convicted in absentia of first-degree murder for the killing of Duhre and conspiracy to commit murder regarding Dhak's death. Following his escape, on 18 October 2022, the RCMP officially named him Canada’s most wanted fugitive, placing a $250,000 bounty on his capture.
Former Solicitor General Kash Heed criticized the investigation, calling it "one of the most embarrassing failures in Canadian law enforcement history."
Many believe he fled to:
The Middle East (Lebanon or UAE)
Mexico or South America
Europe
Final Thoughts: The Alkhalil Family
As of today, Alkhalil remains at large, and his whereabouts are unknown. No confirmed sightings have been reported. Speculation swirls that Alkhalil may have used cartel connections to disappear into the Middle East, South America, or Europe.
But the real question remains: Has his escape fractured the Wolfpack’s power structure, or is he still pulling the strings from the shadows?
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