A man who was shot in the head outside a bar on Winnipeg's Corydon Avenue last spring had been hanging out with the alleged shooter an hour before his death, court documents reveal.

The documents also show in the weeks following Noel Talingdan's killing, Winnipeg police went to great lengths to identify two suspects — including putting a tracking device on a vehicle, using cell site simulators and analyzing "distinctive" elements of footwear worn by the shooter seen in a surveillance video.

Talingdan, 37, and a 28-year-old woman were shot outside Bar Italia around 12:40 a.m. on May 28, 2018.

Talingdan was rushed to hospital in critical condition but died two days later.

A woman he had been talking to was shot in the leg. She was treated and released.

Police have since charged Eric John Boyle, 31, and Joshua Lucien Peter Turner, 25, with first-degree murder and attempted murder.

Noel Talingdan, 37, died after being shot outside Bar Italia in May 2018. (no2ramirez/Instagram)

In a sworn affidavit to the courts for authorization to track Boyle's phone, officers said that the night of the shooting, Talingdan got into an argument with people known to him.

Police say both the shooter and the victim were suspected drug traffickers.

When the investigation began, detectives didn't know who was responsible for the shooting or if either of the victims had been targeted.

Court documents obtained by CBC News show police relied heavily on footage captured by security cameras at Bar Italia and on eyewitness statements to help piece together the events leading up to the shooting.

Security video showed from the time Talingdan arrived at Bar Italia — around 10:45 p.m. on May 28 — he socialized with a number of people he knew, including Boyle, the court documents show.

In court documents, Winnipeg police say Eric Boyle was seen talking to Talingdan the night of the shooting, and that the two even played a game of pool. (Winnipeg police affidavit)

Talingdan and Boyle not only talked at the bar, but also played a game of pool together.

A friend of Talingdan's later told police Boyle was being aggressive during the game and kept saying to Talingdan "we're brothers," according to the documents, although no context was offered for that statement.

Talingdan targeted: court documents

After playing pool, Boyle met up with another man for about 15 minutes inside the men's washroom, the documents show. The two left the bar and met with a third man on the sidewalk outside.

That was around 11:48 p.m., and police said cameras caught the three men walking toward McMillan Avenue, a block over from Bar Italia, according to the court documents.

Police said just after midnight, a woman who came to the bar with Boyle earlier in the night got a text message, walked to her vehicle and left.

"Based on Boyle's behaviour, and that of the unknown female that arrived with him, I suspect that Boyle messaged her and told her to leave" before Talingdan was shot, police said in the court documents.

Around 12:30 a.m., Talingdan and a woman walked toward a park across from the bar to do a drug deal, the documents allege. The woman had been asked by someone she was with if she knew where to get cocaine, she later told police.

"She saw Talingdan nearby and knew that he often has stuff on him. She was given $60 to go buy drugs and approached Talingdan," the court documents said.

Security cameras captured two men on the boulevard outside Bar Italia around 12:30 a.m. on May 28. One of the men pulled out a gun and fired a number of shots. (Winnipeg police affidavit)

Police said a black SUV — which they believe the suspects were using — was parked on McMillan just past Cockburn Street.

Around 12:35 a.m., witnesses said two men — one wearing a white sweater and one wearing dark clothing — were seen standing in front of the SUV. They walked toward Bar Italia and were seen standing on the boulevard north of the bar talking to one another. One of the men appeared to be texting on his phone, the documents say.

At the same time, Talingdan and the woman at the park had finished the drug deal and were walking back toward Bar Italia, where the two men were waiting, the documents say.

Police said one of the men pulled out a gun and fired four to five shots toward the patio, striking both Talingdan and the woman. The suspects ran to McMillan and got into a waiting black SUV.

Police said in the court documents that security cameras captured a black SUV circling Bar Italia about 30 minutes before the shooting. They also said the two men charged in the Talingdan's death got into a waiting black SUV after the shooting. (Winnipeg police affidavit)

Staff at Health Sciences Centre found seven to eight small baggies of what they believed was meth in Talingdan's pocket.

Court documents said he had been arrested in April 2018 for possessing cocaine for the purpose of trafficking. The charge was still before the courts when he died.

Witness believed man 'called in a hit'

A witness told police that prior to the shooting, she and two friends left the patio to grab cigarettes from her car, which was parked on McMillan.

As they cut through a nearby park, she noticed an intoxicated man talking on his cellphone. He appeared to be very angry, she told police. She told them she heard the man say "he's going to get it" or "he's going to get hit," according to the court documents.

The woman also told police about a dark-coloured SUV parked and running on McMillan. She said she saw "two sketchy-looking guys" get out of the vehicle and walk toward Bar Italia, the court documents said.

She heard three gunshots and saw the same two people who got out of the SUV running back to the vehicle, she told police.

"She believed the guy in the park called in a hit," the court documents said.

Shoes had 'distinctive tongues'

Police viewed surveillance video, and compared the footwear of the shooter in the video to Boyle's shoes.

"They are both wearing very similar white shoes, with distinctive tongues. I believe that these are the same shoes and that Boyle is the shooter," the court documents said.

In court documents, Winnipeg police say they watched security video and compared the footwear of the shooter to Eric Boyle's. Police said both were wearing very similar white shoes, with distinctive tongues. (Winnipeg police affidavit)

The investigation was dubbed Project Cherokee, named after the dark SUV — a black Jeep Cherokee — parked on McMillan.

Days after the shooting, police got a warrant to enter an autobody shop and covertly examined the Cherokee. They later returned to put a tracking device on it.

In court documents, police said they got a search warrant for Talingdan's two phones but were unable to unlock them.

They also applied for, and were granted, a number of other warrants in the investigation — including permission to deploy a cell site simulator to locate Boyle's cellphones.

Cell site simulators — also known as StingRays or IMSI catchers — are devices used by law enforcement that simulate a cellphone tower to intercept metadata, or cellphone communications.

The metadata intercepted can be used by police to identify and locate a specific phone.

Driver paid to take suspect to Corydon

In late June, police arrested a woman who the court documents say was driving the Jeep Cherokee the night of the shooting. She told officers she got a Facebook message from a man she knows as "Tin Tin" (later identified by police as Joshua Turner, one of the two men accused, according to the documents).

The woman told police he asked her for a ride and offered her $100. She took her husband's Jeep and drove him and another man, known to her as "Patches," to the Corydon area to meet their friend at Bar Italia.

When they got close, a man she didn't know approached the vehicle and began talking to Tin Tin, saying "nobody disrespects me like that," according to the court documents.

A dark truck pulled up behind them and a woman got out and started talking to the man — who by that point was sitting in the Jeep. Police said the woman handed him something wrapped in a glove.

According to the affidavit, Patches said "I'm not going to do this. I just had a baby."

The man asked Patches for his hoodie and put it on. He and Tin Tin got out of the Jeep and walked toward Bar Italia. The driver said she heard shots fired and the two men came running back to the vehicle, yelling at her to drive.

Police said the woman later identified the man in a photo gallery as Boyle.

In late June, police tracked Boyle's phone to a home on Winnipeg's Alexander Avenue. He was arrested and charged with first-degree murder and attempted murder.

Turner was located and arrested in mid August. He's also been charged with first-degree murder and attempted murder.

Both will be tried together in January 2020. Their trial is scheduled to last three weeks.