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A reward poster for the arrest of Ryan James Wedding at a Justice Department news conference announcing his indictment. He was charged with murder and money laundering in connection to a drug trafficking organization.Andrew Harnik/Getty Images

The moment Ryan Wedding’s life pivoted from one kind of white powder to another can be traced to the chilly slopes of Salt Lake City, on Feb. 14, 2002. The 20-year-old Canadian snowboarder was already being discussed as a superstar in the making, and was now preparing for his first Olympic qualifying run in the parallel giant slalom.

He had been groomed from a young age for this chance, after growing up near Thunder Bay in a family that ran the Mount Baldy ski club, with multiple competitive skiers in its ranks. Mr. Wedding had joined Team Canada at the age of 15 and raced around the world, from the Andes to the Alps.

But under the bright Olympic lights, the young man faltered; he finished about a second off the pace for the final round that day, washing up in 24th place. It was for all intents and purposes the end of his snowboarding career and the beginning of another, much darker path.

Before long, Mr. Wedding would allegedly begin his second career as an international drug kingpin, one that would ultimately see him placed on the FBI’s Ten Most Wanted List, with a US$15-million reward attached to his name; compared with Pablo Escobar and El Chapo Guzman by top U.S. law enforcement officials; and allegedly responsible for a cocaine-trafficking network bringing in US$1-billion a year in revenue.

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Mr. Wedding competes in the qualifying round of the men’s parallel giant slalom snowboarding event during the Salt Lake City Winter Olympic Games.Adam Pretty/Getty Images

He would be accused of ordering the killing of numerous rivals and associates, including a key government witness in the case against him. In the criminal underworld, he would be known variously as El Jefe (The Boss) and El Toro (The Bull).

On Wednesday, the U.S. Justice Department announced the arrest and planned extradition of seven people across Canada linked to the killing of that government informant in January, the latest roundup of Mr. Wedding’s alleged subordinates in what the FBI has fittingly called Operation Giant Slalom.

Still, Mr. Wedding himself remains at large, suspected of living under the protection of the Sinaloa cartel somewhere in Mexico. What follows is a timeline of the former Olympian’s alleged transformation into one of the world’s most notorious cocaine traffickers.

Sept. 22, 2006: The RCMP raided a five-acre property in Maple Ridge, B.C., known as Eighteen Carrot Farms, after a tip that it housed a marijuana grow-op. Behind a thick wall of trees and an imposing gate, Mounties discovered a vast operation even by the standards of cannabis country: 6,800 pot plants and almost 40 kilos of dried weed, with an estimated street value of $10-million, according to local media reports.

A search warrant application tied the property to Ryan James Wedding.

The RCMP did not feel that they had enough evidence to lay charges after the Maple Ridge raid.

By 2006, Mr. Wedding had dropped out of Simon Fraser University, worked as a bouncer at nightclubs in Vancouver, and had some minor success in real estate investment with the help of a loan from his father, according to profiles in Rolling Stone and Toronto Life magazines.

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Mr. Wedding in an undated FBI handout photo. He was arrested in June, 2008, along with a Canadian associate for attempting to buy 24 kilos of cocaine from a police informant in San Diego.Supplied/The Canadian Press

The snowboarder seems to have been lured into the world of drug trafficking by his brushes with high-rolling gangsters at the clubs where he worked, and the aura of easy money floating around the B.C. bud craze that was then seeing the province’s prized cannabis crop sell for astronomical prices in the U.S. market.

June 13, 2008: FBI agents from the San Diego Field Division arrested Mr. Wedding and a Canadian associate for attempting to buy 24 kilos of cocaine from a police informant. The sting had been set up to target the Vancouver-based Akhundov drug-trafficking organization, for which Mr. Wedding allegedly worked. He had flown to southern California with the intention of smuggling the cocaine into Canada but didn’t make it out of the Hampton Inn parking lot, where he was arrested, according to a sworn statement of fact from the FBI agent presented in court.

Mr. Wedding spent nearly two years in a San Diego jail awaiting trial, which his family attended, and was ultimately convicted of conspiracy to distribute cocaine. He claimed to be remorseful during his sentencing hearing, telling the judge, “As an athlete, I was always taught that there is no second chances, and, well, I’m here asking for exactly that.”

April 21, 2015: Again, Mr. Wedding found himself caught in a wide-ranging police sting, this time back in Canada. While living in Montreal after being released from prison and deported in 2011, he came to the attention of the RCMP’s Operation Harrington investigation. He was alleged to have worked with the notorious Sinaloa cartel to import some $750-million worth of cocaine from Colombia and Mexico into Canada, including at least one plot involving shipping the drug from the Caribbean to Atlantic Canada before transporting it by truck to Montreal.

Court documents filed in Ontario and Quebec describe Mr. Wedding as the “man in charge” of the scheme, which was ultimately foiled by an undercover police officer known as Joe, posing as a broker who provided shipping services to drug runners.

Explainer: Who is Ryan Wedding, the former Canadian Olympic snowboarder on the FBI’s Most Wanted list?

By the time Mounties descended on Mr. Wedding’s network, in April, 2015, they were able to seize 212 kilograms of cocaine and arrest nine people. But “the man in charge” was gone, having likely fled the country with the help of the Sinaloa cartel. The RCMP has considered him a “fugitive from justice” ever since.

2015-2024: For almost a decade, Mr. Wedding virtually disappeared from the public record. Authorities believe he was mostly living in Mexico, building a vast drug-trafficking empire shipping US$1-billion worth of narcotics across international borders every year.

U.S. indictments from 2024 and 2025 detail how the gang allegedly used depots in southern California and Ontario-based long-haul trucking companies to move cocaine from Mexico into Canada, some times hundreds of kilograms at a time, before employing the Hells Angels and others to distribute drugs on the ground. (The allegations in the recent U.S. indictments have not been tested in court.)

Authorities believe Mr. Wedding carefully laundered his enormous profits using methods old (an ancient South Asian cash transfer system known as hawala) and new (hundreds of millions of Canadian dollars funnelled through a variety of cryptocurrency wallets).

He paid associates in drugs and expensive watches, and stored cash in a huge fleet of luxury motorcycles and cars around the world through a broker known as “The Italian,” according to an arrest warrant filed in Quebec Superior Court this week.

The same warrant claims that Mr. Wedding dated a woman in Mexico City for about a month in 2022, and more recently offered to pay for her breast implants if she would lure a suspected informant to the site of his planned assassination. (She declined.) Another woman in his orbit was said in the warrant to have been responsible for providing Mr. Wedding and his associates with prostitutes.

Above all, Mr. Wedding’s world was extremely violent. He allegedly cultivated a group of hitmen and sent them to track and kill people around the world. At least one of the organization’s assassins was allegedly flown to Mexico for weapons training before allegedly shooting a man dead in his driveway near Niagara Falls. The gang is linked to at least a half dozen murders and is likely to have committed more, according to U.S. indictments and arrest warrants.

Victims were not limited to rivals in the drug trade. An alleged fellow trafficker in Miami told U.S. prosecutors that Mr. Wedding threatened to kill his mother if he did not pay for five kilograms of cocaine. In 2023, two members of the Sidhu family in Caledon, Ont., were shot dead allegedly by a member of the Wedding organization in an apparent case of mistaken identity.

Spring 2024: Investigators had a breakthrough when a Montreal-born Colombian-Canadian trafficker and member of the Wedding gang named Jonathan Acebedo-Garcia agreed to become a government informant, the arrest warrants allege. Operation Giant Slalom had begun. With the help of “Jon,” U.S. and Canadian police conducted a series of raids on L.A. safe houses and the Brampton trucking company that Mr. Wedding had allegedly been using to bring cocaine into Canada. They arrested Hardeep Ratte and Gurpreet Singh, the trucking magnates, and seized US$30-million of drugs – just scratching the surface.

Who are the Canadians facing charges connected to Ryan Wedding?

Oct. 17, 2024: The U.S. Justice Department drops a bombshell: a superseding indictment charging 16 defendants linked to the Wedding organization, alleging that the gang committed at least four murders in pursuit of their ambitious drug-smuggling operation. American authorities announced that they had, notably, arrested Mr. Wedding’s alleged second-in-command, Andrew Clark, a 34-year-old former elevator mechanic from Toronto now nicknamed The Dictator by his fellow narcos, who had been nabbed by the Mexican navy in a Guadalajara restaurant earlier that month. (Mr. Clark is currently awaiting trial in California, where he is charged with drug trafficking, murder and conspiracy to commit murder.)

Fall 2024: After the indictment and police roundups, Mr. Wedding allegedly went on the hunt for a “rat” in his midst. It did not take long to find his man, according to the Quebec arrest warrants. A Montreal hitman, Atna Onha, texted Mr. Acebedo-Garcia and asked point blank if he was the informant. “Jon” confirmed that he was. Deepak Paradkar of Mississauga, Ont. – allegedly a Wedding organization lawyer whose social-media handle was once “cocaine_lawyer” – “advised” Mr. Wedding that if the informant was killed, it would make the case against his organization fall apart, according to the U.S. Department of Justice.

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Mr. Wedding is seen top left, with 15 other defendants who were charged in a 16-count superseding indictment for allegedly running and participating in a transnational drug trafficking operation that routinely shipped hundreds of kilograms of cocaine, from Colombia, through Mexico and Southern California, to Canada and other locations in the United States.Damian Dovarganes/The Associated Press

The alleged kingpin decided he would spend up to US$5-million to carry out the hit, and Mr. Onha began tracking down Mr. Acebedo-Garcia’s girlfriend in Colombia, according to the arrest warrant. Another gang member allegedly paid a now-defunct website called the Dirty News $10,000 to post photos of their target, along with the caption, “This guy single handedly ratted out one of the strongest underworld networks that this world has seen. Good chance he’ll never be found again.”

Jan. 31, 2025: A man holding a silenced handgun walked up behind Mr. Acebedo-Garcia while he was eating lunch at a restaurant in Medellín, Colombia and allegedly shot him in the head five times, before fleeing on a motorcycle. As described in the arrest warrant, the lead witness in the trial of Mr. Clark was now dead. The hit squad was paid US$500,000 for the job, according to arrest warrants; Mr. Ohna of Montreal received $150,000 and 30 kilos of cocaine, worth well more than a million dollars.

March 6, 2025: Allegedly murdering a state witness had the expected effect: the heat on the Wedding organization increased exponentially. The U.S. government increased the reward for information leading to Mr. Wedding’s arrest to a staggering US$10-million from US$50,000. The FBI placed him on their Ten Most Wanted list. “There is nowhere safe for Wedding to hide,” said Los Angeles deputy police chief Alan Hamilton.

Nov. 19, 2025: The RCMP swept up Mr. Onha, the alleged Montreal hitman, and Mr. Paradkar, the Toronto-area “cocaine lawyer,” among others. U.S. Attorney-General Pam Bondi and FBI Director Kash Patel gave a lengthy press conference flanked by more than a half-dozen leading Canadian and American law enforcement authorities, calling Mr. Wedding and his crew “monsters,” and vowing to bring them to justice.

Still, they acknowledged that the man his associates call El Jefe remains at large, probably in Mexico protected by the Sinaloa cartel. One ominous sign for Mr. Wedding has emerged in court documents related to the arrests: the U.S. government has flipped another member of the Wedding organization, and have met several times with their new informant.