Up-and-coming rapper Pressa is on the verge of escaping the poverty and violence of his Driftwood neighbourhood, but his past hangs over him

UPDATE: Quinton Gardner no longer faces any charges with respect to the kidnapping allegations. All charges against him were dismissed at a preliminary inquiry in Dec. 2017.

The rapper Pressa paces across a grand stage. It is the first time he has opened for Drake. It is also his first-ever public performance.

UPDATE: Quinton Gardner no longer faces any charges with respect to the kidnapping allegations. All charges against him were dismissed at a preliminary inquiry in Dec. 2017.

The rapper Pressa paces across a grand stage. It is the first time he has opened for Drake. It is also his first-ever public performance. He is 20 years old, perhaps 130 pounds – gold chains included – and works the crowd like a old pro, rattling off rhymes firmly grounded in the Toronto neighbourhood where he was born and raised. “Sleeping in my North Face, we come from north Jane,” he raps.

Spectators turn away, talk amongst themselves. Quinton Armani Gardner is a long way from home. This is the sold-out Barclaycard Arena in Birmingham, England (capacity: 16,000). The Brits came for that other Torontonian.

Mr. Gardner soldiers on, serene. He can revel in the mere act of being here – here on this overseas stage, here rather than jail with his father and brother, here rather than riddled with bullets like his friend and collaborator Robin Banks, who narrowly survived a nightclub shooting this month.

His unlikely ascent through the ranks of the city's underground rap scene began last year with Deadmihana, a track about smoking a dead man's marijuana, released under his stage name, Pressa. The video has since topped 1.6 million YouTube views. More tracks and more acclaim followed. But just as his career appeared destined for stardom, Toronto police named him as one of the leaders of the Young Buck Killers, a gang allegedly involved in a terrifying downtown shootout that spiralled into a case of kidnapping and sexual torture, part of it broadcast over social media. The allegation has not been tested in court and Mr. Gardner's lawyer maintains his client's innocence.

Pressa now stands at a make-or-break moment. He just finished opening for Drake's European swing. Next up is a warm-up spot with Giggs, a chart-topping British rapper. He has charisma and a head for business.

"Pressa is on everybody's radar," said Eb Reinbergs, entertainment lawyer and founder of the Canadian Urban Music Conference. "He's one of the top two or three hottest rappers in city."

And yet, by next year he could just as easily be sitting in a jail cell as in a VIP room.

It's possible he's earned both.

'He will never be a kid again'

On June 15, 1996, Mark Anthony Gardner shot a man through the heart.

Back then Mr. Gardner was known simply as "Prestige." His lengthy record of convictions for drugs and violence earned him a measure of respect in the north Toronto neighbourhood where he lived. On that June night, he went to a community dance, where he encountered a long delay in entering the hall. He vented his anger at a 26-year-old volunteer security guard named David Williams, who spent his days working for the city as a youth worker. Mr. Gardner told the security guard he was going to kill him, calmly retrieved a handgun from his car, returned to the dance and fired a single shot.

"I said I'd shoot you," he reportedly told the dying man, before fleeing the scene.

A judge called it a "deliberate execution" and sentenced Mr. Gardner to at least 15 years in prison for second-degree murder.

Quinton Armani Gardner was 36 days old when his father pulled that trigger. The murder sentence created a financial crunch in the Gardner household. During a court hearing, Quinton's mother submitted a letter saying that money was tight. She was faced with a dilemma: On one hand, she needed to leave the house to earn money. On the other, she needed to stay home to keep her sons – Quinton and his three-year-older brother Chermar – away from the criminal influences that pervaded their Driftwood neighbourhood, situated just north of the Jane/Finch intersection.

The boys would have to learn to navigate a world where good deeds aren't always rewarded.

One school teacher, Devon Jones, could see that the Gardners were in a vulnerable position. In more than two decades teaching in the Driftwood area, Mr. Jones has witnessed countless young men turn to crime as a solution to their marginal circumstances. He likens the neighbourhood to a prison where young people become habituated to poverty and violence.

City of Toronto figures show that the Driftwood area is the least livable community in the city, based on an aggregation of scores for education, employment, mortality and other criteria. Unemployment is roughly twice the national average. One-third of residents collect social assistance. On one track, Pressa says he comes from a "crazy block" where you need to be prepared to "die for your necklace."

Today, Mr. Jones avoids speaking directly about the Gardner's circumstances, but talks openly about one of their close friends, Kwasi (Wassi) Skene-Peters. Mr. Jones recalls one Saturday in 2005, when gunfire erupted in Driftwood leaving a young man dead on a footbridge. He watched Wassi, then a preteen, stumble across the bullet-riddled body. "I thought to myself, 'He will never be a kid again,'" Mr. Jones said. "There's no way you can see something this grotesque as a child and go on to become a normal functioning human being."

Mr. Jones encouraged Chermar and Wassi to join the Youth Association for Academics, Athletic and Character Education (YAACE), a group he co-founded after the footbridge incident to steer at-risk kids off the streets and into school. On at least one occasion, he took Chermar and Wassi to a camp outside the city to remove them, for a time, from the life that was beginning to envelop them.

But while Mr. Jones's tireless efforts put hundreds of children on a path to post-secondary education, he could not save Wassi and Chermar, who skipped school to work part-time before entering the drug trade full-time.

By the age of 18, Chermar was manufacturing and distributing crack cocaine. By the fall of 2011, Toronto Police considered Chermar the leader of a violent gang called the Young Buck Killers, which ran drugs and guns throughout the Greater Toronto Area. The gang was subsequently linked to more than 60 arrests in an organized crime raid dubbed Project Marvel.

In court, evidence linked handguns found in the Gardner home to four separate shootings. Confidential informants told police that Chermar led the Young Buck Killers while Quinton was "second in charge" and "next in line," according to a judge's written decision.

In 2014, Chermar was convicted on 14 gun, drug and gang charges. At a hearing to determine his sentence – a hearing Mr. Jones attended, as he has done so many times for the young men he cares for like a parent – he took full responsibility for his crimes and pleaded for lenience.

"I was deceived by the generations that preceded me with the cars, the clothes, the women and the fancy jewellery that this type of lifestyle was a life to live, and it was also the shortcut around the hard work and toil," he said, before expressing hope that Quinton would avoid his example.

"I feel like I failed my little brother … And if I don't change my life that kid is never going to change his life, and I have to change for him." He was handed a 10-year sentence.

Stories of the streets

Pressa's friend Wassi, the man who was the boy who witnessed the shooting on a footbridge, suffered a worse fate. In 2015, he died, shot in a firefight with police outside a nightclub in the downtown core.

The Special Investigations Unit, the oversight body that probes all deaths involving police in Ontario, determined that Wassi had fired the first shot and that officers had acted in self defence.

For Mr. Jones, the death was a particularly sad addition to a body count he cites often: 151 homicides of school-aged children (21 and under) in Toronto since 2007.

"It hurt," Mr. Jones said. "It really hurt. That's your kid. It's your kid, man."

Shortly after the death, a music video appeared on YouTube entitled Wass Gang – a tribute to Wassi. Shot cheaply among the Driftwood social housing units, it featured Robin Banks, an emerging Toronto rapper from the Driftwood area and Pressa in his first big role. He wore a Canada Goose coat, rode a motorcycle and rapped in a high, reedy voice. They rhymed of "pulling triggers" if disrespected and "kidnapping drug dealers."

Since Wass Gang hit YouTube in 2015, Pressa has uploaded an album's worth of material. Compared to the vulnerable strain of rap Drake has introduced to the genre, Pressa is a throwback. His rhymes revolve around guns, drugs, cars, women and his incarcerated family members. He has been compared both physically and artistically to Eazy-E, the diminutive godfather of gangsta rap.

"'Cause I'm realer than death, there ain't no realer than me," he says on Orange Jumpsuit. The lyrics suggest a deep immersion in a violent criminal lifestyle. They seem to glorify gangsterism. But they can also be interpreted as a first move towards escaping that life through music. On Twitter, he refers to his new career as "a way out."

"They both tell stories of the streets where they come from," said Mr. Reinbergs, the entertainment lawyer, whom Mr. Gardner has sought out for career guidance.

"Sound-wise, the attraction is how real they both are. They tell no lies. Hip-hop doesn't allow for that. Artists trying to reflect something they are not are torn down. Just look at Vanilla Ice."

Occasionally, Pressa drops the swagger and allows himself to dwell upon the loss of his friend Wassi and the sadness that accompanies the life he was born to:

"I miss my bro so everything I do is for him

The demons steady callin'

These demons get annoying."

Deadmihana, another YouTube hit, truly thrust Pressa to the forefront of the city's underground rap scene when it was released in January, 2016. He soon earned acknowledgment from the likes of the Weeknd, Meek Mill and the 6-God himself, Drake.

But in Toronto's underground rap scene, online views rarely translate into revenue. There is an ample fan base, but few willing concert venues and even fewer willing radio stations.

"Toronto is messed up," said Emmanuel Uzaka, who runs a podcast dedicated to the Toronto rap scene called It's Too Real. "You'll see a flyer for a concert here and there and then it always gets cancelled. There are a lot of talented people rapping in Toronto, but very few stars making a living. There is no infrastructure, no places to play."

Pressa found a way around these hurdles. From the moment a nascent fan base began forming around his unique sound, he developed a label, Blue Feathers Records, and a website to sell branded merchandise. He's cultivated a vibrant social media presence and reached out privately for business advice.

"I have found him to be a respectful young man and a very business minded young man, impressively so," Mr. Reinbergs said. "Those are two things that separate him from lot of young artists I work with. At beginning of your career, to create your own brand, that's just remarkable."

He seemed poised to vanquish his demons. And then it all fell apart.

'A lot resting on those shoulders'

At 4:44 a.m. on April 19, four young men in dark hoodies stepped out of an elevator in a downtown Toronto condo building. Police allege they were headed to a party hosted by the Young Buck Killers.

Security cameras in the elevator capture the moment they turn left down a hallway then immediately retreat in the face of gunfire. A firefight ensues.

Amazingly, no one is seriously hurt. But, according to police, the Young Buck Killers were not content to call it even.

They allegedly kidnapped two teenagers they believed were affiliated with a rival gang, the Queen's Drive Crips. The duo was beaten, coerced to play Russian roulette and forced to perform sex acts. Video clips of the brutality were broadcast by social media, community sources told The Globe. Eventually, a ransom was paid and the teens were returned to their families.

On April 24, officers in the Jane-Finch area, chased down and arrested Mr. Gardner. In a news conference, Staff Inspector Mike Earl, head of the hold-up squad, named Mr. Gardner as one of the "instigators" but not the "ringleader" of the kidnapping plot.

That characterization doesn't square with the evidence Mr. Gardner's lawyer has seen. "It is not alleged that he is an instigator," said his lawyer, Anthony Robbins, who could not share details with the case pending. "He is alleged to be a minor part in the incident. He will, hopefully, be exonerated at trial."

Pressa declined The Globe's interview requests.

While in custody at the Toronto South Detention Centre, Mr. Gardner was involved in a fight with rival gang members, the results of which are disputed.

"Now the rumors 'round the streets that I broke my two arms," he raps on Orange Jumpsuit, "when I sent him to ER."

Many further details emerged during a bail hearing, but they remain under a publication ban. There is one very telling detail on the public record, however. The justice of the peace who heard the bail arguments didn't think Mr. Gardner's actions warranted further incarceration and granted bail. And weeks later, the Crown agreed to a major bail variance that allowed Mr. Gardner to travel to Europe with Drake.

"It encourages him to work," said Mr. Robbins, his defence lawyer. "It works to everyone's benefit."

His next court date is scheduled for October with a preliminary inquiry set for December. Much hinges on the outcome. "With a criminal conviction he wouldn't be able to cross the border," Mr. Uzaka said. "He'd be stuck here with two million YouTube views and no place to go. If he can't make it, the door closes for so many people behind him. I really feel that. There's a lot resting on those shoulders. I just hope he gets what he deserves."

Several days ago, the neighbourhood demons came calling once again. Early on the morning of April 3, Robin Banks was shot outside a Woodbridge nightclub and rushed to hospital with life-threatening injuries. As Banks recovered, fans and friends looked to Pressa. His response would be telling. Would he pledge the kind of violent retribution he preached in Wass Gang, the track he'd recorded with Banks? Or would a new Pressa step forward, the one who knows his career depends on abiding the law?

“I would appreciate it if all my followers can pray for @RobinBanksTT,” he tweeted. “#stoptheviolence.”