The assassination of Nicolo "Nick" Rizzuto, 86, inside his Montreal mansion is thought to be the coup de grâce against the once-mighty crime family that, for 30 years, dominated Montreal's underworld. Rizzuto was executed at sundown, Nov. 10, 2010 in front of his wife and daughter by a sniper bullet shot from outside the home.

"With the death of its historical patriarch, the clan from Sicily has suffered a blow that could prove fatal," Italy's Ansa agency reported.

Timeline for the Rizzuto clan

1924: Nicolo "Nick" Rizzuto is born on Feb. 18 in Catolica Eraclea, in southern Sicily. He marries into the Italian mob by wedding Libertina Manno, daughter of a Mafia boss in the region. Their first son Vito is born Feb. 21, 1946.

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Nicolo Rizzuto, seen leaving prison in 2008, was assassinated in his kitchen Nov. 10, 2010. ((Canadian Press))

1954: The Rizzutos sail to Canada and settle in Montreal.

  • The senior Rizzuto becomes an associate of the Calabrian Cotroni crime family, which had strong links with New York's Bonnano family and controlled the majority of Montreal's drug trade mid-century. Nicolo Rizzuto flees to Venezuela in 1974, where he reportedly builds alliances with the Cuntrera-Caruana Sicilian Mafia clan, and with a Colombian cartel.
  • A turf war between rival Calabrese and Sicilian factions in Montreal comes to a drawn-out climax in the late 1970s when Paoli Violi, head of the city's Calabrian clan is murdered in 1978, along with his three brothers, all linked to the Cotroni and Bonnano families. Their power in Montreal is supplanted by the Rizzuto clan.

1980: Nicolo Rizzuto returns to Canada and hands over the family business to his son Vito. Known as the "Teflon Don," Vito establishes his power while avoiding most criminal charges, except for a two-year sentence he served in 1972 for conspiring to commit arson. He is charged and acquitted in two drug investigations in the 1980s.

1981: Police believe Vito Rizzuto is formally inducted into the powerful New York Bonanno family organization after allegedly helping to murder three of the family's captains who were suspected of plotting a takeover. Authorities start referring to the younger Rizzuto as "Godfather" of the Montreal Mafia, and he becomes Canada's most influential member of the Bonnano clan.

2001: Montreal police say they had have foiled a plot to kill Vito Rizzuto and charge three people.

Jan. 20, 2004: Vito Rizzuto is the only Canadian arrested among 28 members of the Bonanno/Massino family in a massive police crackdown on the Mafia; the others were arrested in New York. They are accused of murdering three of the family's top members in 1981. Rizzuto is charged with conspiracy to commit murder. U.S. prosecutors say the arrests mean virtually every leader in the Bonanno family has either been convicted or is under indictment.

  • U.S. officials immediately ask for Rizzuto's extradition to the U.S., where a conviction could send him to prison for 27 years. Rizzuto's five lawyers said U.S. prosecutors waited too long to charge Rizzuto, claiming the statute of limitations for the alleged crimes had expired. They ask for Rizzuto to be released from jail and financially compensated. Their fight against the extradition order lasts almost three years, and ends in Supreme Court.
  • Vito Rizzuto's arrest marks a major loss for the family's business, experts say. A skilled mediator, Rizzuto was recognized for birthing a strategic alliance between the Mafia and other criminal organizations, including the Hells Angels, Rock Machine and street gangs. Mafia watchers suggest Nick Rizzuto was forced to resume a more active role in the family business in his son's absence.

Aug. 17, 2006: Canada's Supreme Court refuses to hear Rizzuto's appeal of extradition order, clearing the way for him to stand trial in the U.S.

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Vito Rizzuto, the "Teflon Don", is finishing a 10-year prison sentence in the U.S. ((Canadian Press))

Nov. 3, 2006: Bettina and Leonardo Rizzuto launch a $950,000 defamation lawsuit against journalists Lee Lamothe and Adrian Humphreys, authors of a book about their father Vito Rizzuto. The adult children – both practising lawyers –  claim their reputations were compromised by the book's allegations about their family's criminal dealings. 

Nov. 22, 2006: Canadian police round up nearly 100 suspected mobsters in the greater Montreal region, after an exhaustive four-year investigation called "Operation Colisée." Armed with more than a million hours of taped conversations from wiretaps, video surveillance and hidden microphones, authorities arrest high-ranking members members of the Rizzuto clan, including Nick Rizzuto, Paolo Renda, Rocco Sollecito, Lorenzo Giordino and Francesco Arcadi, along with several Trudeau airport employees.

  • The RCMP declares it has penetrated the very heart of the clan. Authorities seize more than $3 million and lay 1,300 charges, including attempted murder, importing cocaine and drug dealing, gangsterism, extortion, bookmaking and possession of restricted weapons.
  • Police say the suspects were running a multi-million dollar online sports betting racket and cocaine trafficking ring.

December 2006: Former Federal justice minister Irwin Cotler orders Vito Rizzuto extradited to the U.S.

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Nick Rizzuto Jr., shown here in a 2007 file photo, was murdered in late 2009. ((Benoit Pelosse/Le Journal de Montreal/Canadian Press))

May 2007: Vito Rizzuto pleads guilty to racketeering charges in connection to the 1981 Brooklyn murders of three renegade captains of the Bonnano family (Dominick "Big Trin" Trinchera, Philip "Philly Lucky" Giaccone and Alphonse "Sonny Red" Indelicato).  

  • Rizzuto receives a reduced 10-year sentence and a $250,000 US fine after admitting in court that he was armed at the murder scene. He is incarcerated in a Colorado prison, eligible for release in 2012.

October 2007: European authorities arrest 17 people in connection to an alleged international Mafia ring believed to be trafficking drugs and laundering money.

  • Italian authorities issue international arrest warrants for Nick and Vito Rizzuto, alleging the son and father managed the operations from their respective prisons. Warrants are also issued for Paolo Renda and Rocco Sollecito. Police seize assets and cash worth about $212 million U.S.
  • "To really impact an organized crime family, you have to get at their money," said organized crime author James Dubro.

January 2008: Authorities lay 100 new charges, mostly possession of proceeds of a crime, against several people arrested during Operation Colisée, including Nick Rizzuto.

September 2008:  In a plea bargain with the Crown, Nick Rizzuto pleads guilty to two gangsterism charges — possession of proceeds of a crime and possession of the proceeds of crime for the benefit of, the direction of, or in association with a criminal organization. Paolo Renda, Vito Rizzuto's brother-in-law, pleads guilty to the same charges.

  • Francesco Arcadi pleads guilty to conspiracy, which includes an admission he plotted to oversee drug smuggling and trafficking, bookmaking and illegal gambling. Rocco Sollecito, Lorenzo Giordano plead guilty to several charges from conspiracy to drug trafficking and extortion. They face sentences ranging from six to 15 years.

October 2008: Nick Rizzuto receives a suspended sentence and three years' probation for his guilty plea to gangsterism charges. He is freed from prison.

  • The Crown admits police did not do enough to follow the money trail during their investigation, and despite all the wiretap evidence they can't link the elderly patriarch to most of the charges.

August 2009: Frederico Del Peschio, an associate of the Rizzuto clan and owner of Montreal restaurant La Cantina, is murdered behind his establishment.

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Paolo Renda is married to Vito Rizzuto's sister Maria. He was abducted in May 2010. ((CBC))

December 2009: Vito Rizzuto's son Nick Jr. is gunned down in broad daylight on a residential street in Montreal's Notre-Dame-de-Grace neighbourhood. Mafia experts say the brazen murder of a low-profile member of the powerful family marks an unprecedented challenge to the clan, and retaliation should be expected.

Feb. 11, 2010: Nick Rizzuto enters a guilty plea to tax-evasion charges. The charges stem from a Canada Revenue Agency investigation for the tax years 1994 and 1995. Rizzuto is accused of failing to declare the interest earned on more than $5 million deposited in three Swiss bank accounts. The Court orders Rizzuto to pay $628,000 in back taxes, a $209,000 fine and administrative penalties.

May 2010: Paolo Renda, Vito Rizzuto's brother-in-law and presumed right-hand man, is abducted from his car on a Montreal street, several months after his release from prison on charges related to Operation Colisee. Renda is believed to have handled finances for the Rizzutos. He is also uncle and godfather to Nick Rizzuto Jr.

July 2010: Reputed mob boss Agostino Cuntrera, a high-ranking Rizzuto associate, is slain in front of his wholesale food business in Montreal's St-Leonard borough, along with his bodyguard Liborio Sciascia. Montreal police say the double killing is linked to a turf war between two rival families.

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The casket of Nicolo Rizzuto is carried out of Notre-Dame-de-la-Défense. ((CBC))

Nov. 10, 2010:   Nicolo Rizzuto, 86, is assassinated at supper time in his northwest Montreal home in front of his wife and daughter. A sniper shoots the crime boss through a double-pane window, killing him with a single round.

Nov. 15, 2010: Hundreds attend the funeral of Niccolo Rizzuto in Montreal, including a crowd of curious onlookers. Police seize an unusual shoebox-sized package containing a note in front of the Notre-Dame-de-la-Defense Church where the funeral was held. Police say the note's contents will remain confidential during the course of their investigation.

Jan. 6, 2011: A funeral home owned by the Rizzuto family, Loreto Funeral Complex, is firebombed in the east end of Montreal. The funeral home hosted several family-related visitations, including that of Niccolo Rizzuto. There were no injuries and police questioned three men.

With files from Radio-Canada, Jonathan Hembry