Nick Chan once controlled one of the most violent criminal organizations in Calgary — the FOB gang.

He was in charge of a large drug network, operated a bawdy house and would pay his gang members to maim and kill rivals, according to court documents obtained by CBC News.

New details are emerging about just how far the leader of the notorious group — which initially stood for "Fresh Off the Boat" when formed in the late 1990s — went to protect himself against police and rival gangs.

The documents suggest Chan's paranoia helped keep him safe from the gang's fierce rivals, the FK — a splinter group that formed because of personal rifts between members of the FOB before the turn of the millennium.

But Chan's eventual downfall came because of the police co-operation of his gang brothers and former wife. Chan is currently in custody and facing several charges, including first-degree murder.

Most other top-ranking founding members of the FOB have either been killed, are in custody or have made plea deals.

Police intercepted phone calls, used surveillance and turned gang members for years to try and bring down Chan and other high-ranking gang members.

"I think that what happens is that members of criminal organizations take extraordinary measures to avoid detection and to avoid being caught," said Insp. Cliff O'Brien, head of the Calgary Police Service's major crimes unit.

"What that means is our investigators have to take extraordinary measures to overcome that."

The court documents were produced by police during their investigation. They include police findings, interviews and expert opinion from the investigations of six slayings in Calgary.

None of the allegations have been proven in court.

The makings of gang leader

As a teenager, Chan started dealing drugs with his younger brother Tim. They would receive drugs from their "uncle" Dau Foo Minh — the leader of an older gang that went by "The Devil Boys" — and sell them on the streets of Calgary.

Chan quickly moved up the ranks, dealing drugs by the kilogram. Chan was considered the leader by the time the group was entrenched in the Calgary drug scene.

There were several other small gangs operating in the 1990s, but two Asian gangs dominated by the early 2000s — the FOB and shortly after the FK, or "FOB Killers."

The gang war between the two groups has been linked to at least 25 deaths in Calgary since 2002.

Chan would develop "flags" or divisions within the gang, each under a separate leader. Some of the divisions had 20 or 30 members. Chan would collect money from each flag, which would be used to pay lawyers, get houses to hide drugs and compensate members for attacking enemies.

All the flags would come together again under Chan by 2009. The FOB had also formed alliances with native gangs — the Red Alerts and Alberta Warriors — inside the Calgary Remand Centre and other Alberta prisons.

The puppet master

The court documents outline how Chan would orchestrate attacks against FK members.

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Hans (Jay) Eastgaard is a longtime friend of Nick Chan and an original FOB member. The former enforcer made a deal with police which will see him avoid jail time — despite his admitted role in a at least three killings — in exchange for his testimony against Nick Chan and other high-ranking FOB members. (Courtesy Calgary Police Service)

FOB enforcer Hans Eastgaard detailed in a police interview how Chan ordered the death of Kevin Anaya in August 2008. Chan planned the attack, chose the gang member to carry it out and gave him a gun.

Anaya was shot and killed while walking to a friend's house for a barbecue in Marlborough.

Eastgaard told police he was paid $10,000 by Chan and another top-ranking gang member, Dustin Darby, to shoot and kill the 21-year-old.

Chan is also said to have instructed the notorious triple slaying at the Bolsa Restaurant on Jan. 1, 2009.

Two masked men entered the restaurant and opened fire. FK member Sanjeev Mann and associate Aaron Bendle were shot several times and died. Bystander Keni Su'a was killed while fleeing the building.

Findings by police conclude each of the shooters was paid $10,000 by senior members of the FOB.

The gangster's wife

Chan married Yongyi Guan in April 2008 in China. Her first application to immigrate to Canada was rejected because Chan did not provide enough tax and employment information.

The couple appealed the decision and was successful. Guan arrived in Canada in February 2012.

The couple’s relationship eventually became abusive, according to Guan. She said there was shoving and slapping once when she brought up suspicions that he was unfaithful. Afterwards Chan bought her a plane ticket back to China and she left Canada in July 2012.

Chan had a CD marked "goofs" that had photos of his enemies on it. Guan saw the photos had "about 10 or more pictures and that some were white and some were Asian."

Guan would tell police that Chan was involved in a variety of businesses, including being a part-owner of a Chinatown club and renting out an apartment building.

She would later tell police that Chan and a female associate operated a bawdy house around 2009 to 2010. According to the documents, Chan told her that he was running five or six prostitutes.  

She says Chan was careful to the point of being paranoid.

He kept multiple pay-as-you-go phones and would always delete text messages and his call history. He carried a personal phone, jail phone, texting phone and lawyer phone.

In one phone call intercepted by police, Chan told an associate why he was taking so many steps to cover his trail.

"Everybody's trying to plant moles, like cops are trying to plant moles," he said.

Guan said she did not know about Chan's position in the gang but "could tell by the tone in his voice that he was not low level" when he received calls from others in jail, according to the document.

He "drove around in circles to avoid being followed" and would not discuss much on the phone, she said.

Chan also kept a place at an apartment building where he would enter and exit the elevator on different floors from where he lived. He would even stick a piece of paper in the door frame to monitor if anyone had entered his suite.

As for Chan's motivations, Guan said he wanted revenge, war and "guns and more shootings."

Guan returned to Canada in November 2012 and spoke to border agents about Chan. She told Canada Border Services Agency officers she was filing for divorce because Chan was unfaithful.

She spoke with CBSA officials again in April 2013, calling Chan "a violent individual" that is involved in the drug trade.

Near-death attack

Chan was leaving the Community Natural Food Store in Calgary's southwest on April 23 when he was attacked by two men, who stabbed him repeatedly. 

Chan was able to drive away and was found by emergency personnel in the area with seven stab wounds.

The injuries were life-threatening and required emergency surgery.

Billy Ly, who is known to have FK ties, has been charged with attempted murder in the attack, according to documents before the court.

The fall

Despite his near-death experience, Chan's reign as leader of the FOB continued.

His arrest this July was because of statements to police from his longtime friend Eastgaard.

Eastgaard provided testimony to police, which eventually led to the arrests of Chan and several other senior members of the FOB.

Chan was taken into police custody on July 18. His charges include conspiracy to commit murder, instructing a criminal organization — the first time Calgary police have ever laid the charge — and two counts of first-degree murder.

He is now awaiting trial.

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