Four murders, an executed key witness, a fugitive ex-Olympic snowboarder accused of ruling a $1-billion cocaine empire — and one of his alleged deputies keeps looking back at his wife to smile.

Gurpreet Singh, 30, was in a downtown Toronto prisoner’s box seeking bail Tuesday as he fights extradition to the United States on charges he helped arrange the transport of huge shipments of cocaine into Canada on behalf of Ryan Wedding, aka El Jefe, a former snowboarder at the 2002 Olympic Games in Salt Lake City, Utah, who U.S. authorities claim is the head of a drug empire.

Their investigation, dubbed “Operation Giant Slalom,” alleges Wedding, his lieutenant and fellow Canadian Andrew “the Dictator” Clark, and others conspired to ship hundreds of kilograms of cocaine from Southern California to Canada through a Canada-based drug transportation network run by Hardeep Ratte, 45, of Brampton and his nephew, Singh.

And this cocaine enterprise didn’t play around — American authorities allege Clark and Wedding ordered four hits on their enemies in Canada — including the murders of Jagtar Sidhu, 57 and Harbhajan Sidhu, 55, who were visiting their daughter in Caledon and were mistaken for a courier who had made off with one of their drug hauls.

In new details revealed in court, Crown attorney Melissa Insanic said the U.S. record of the case estimates the street value of the two drug shipments that Singh allegedly agreed to move for Wedding into Canada was about (US)$9 million and the going rate of payment for Singh and Ratte was between (CDN) $175,000 and $225,000 for each haul. He likely faces a term of 20 to 25 years in prison, if convicted.

Ratte has already had his bail hearing and is awaiting judgment.

The Department of Justice and other U.S. law enforcement officials are seeking former Olympic Canadian snowboarder Ryan James Wedding for drug trafficking and murder.Photo by Handout /FBI

The Crown, who opposes Singh’s bail, alleges he has “connections to enforcers or hitmen,” is involved in a scheme to ship high-end cars through Montreal to Dubai and has connections to organized crime in Dubai, including the violent Kinahan gang and routinely travels there.

Also, encrypted communications show Singh travelled to Mexico in July 2024 to meet with a cartel leader to settle a drug debt, the prosecutor said, and was kidnapped and held until Wedding allegedly negotiated his release.

“The allegations are that Mr. Singh participated in arranging for the cross-border import-export of large quantities of cocaine in association with a criminal organization,” Insanic said. The indictment zeroes in on February to April 2024 when the feds had someone on the inside.

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Insanic told Superior Court Justice Michael Dineen that a cooperating witness (CW) who trafficked drugs with Wedding agreed to assist American law enforcement in 2023. At their direction, the informant met with Clark and Wedding in Mexico City in January 2024 where Clark told him he shipped between 2,000 to 3,000 kilos a month from their stash houses in L.A. to Canada.

“Clark directed the CW to contact Singh to arrange for the transport of cocaine into Canada and told the CW to offer to pay Ratte and Singh a rate of between $175,000 and $225,000 Canadian per shipment.”

On Feb. 22, 2024, the Crown said Singh picked up the CW from the Toronto airport in a black Cadillac Escalade and took him to meet his uncle at an auto collision centre to discuss the arrangement — a meeting that was being covertly recorded by the RCMP.

On March 1, Insanic said, Wedding messaged the CW that he had a load of cocaine ready for transport in L.A. and over a group chat, he passed on the information to Singh and Ratte that 293 kilos packaged in 20 boxes were ready to move.

Ratte messaged back that his courier would arrive in L.A. on March 3 and that evening, Singh sent the CW the courier’s phone number and a serial number on a dollar bill to use to verify the courier’s identity, the U.S. record alleges. The CW passed on the info to Wedding but substituted a phone number that would be monitored by the American authorities.

U.S. law enforcement observed the meeting between the couriers in San Bernardino where the boxes of cocaine were transferred between vehicles and sent on their way to Canada, Insanic said.

A second shipment was similarly arranged with Singh in April 2024, she said — only this time the rendezvous with Singh’s alleged courier, Rakhim Ibragimov, ended with his arrest and police seizure of 375 kilos of cocaine in Riverside, Calif.

Last week, one of Singh’s lawyers said the key prosecution witness in the case would no longer be able to testify; the Toronto Star has reported the CW was recently murdered in Colombia.

The bail hearing continues.

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