The young men who call themselves Gangster Disciples skirted by an empty lot. They marched past a “Stop the Violence” mural painted on a corner store, coming to a halt when they saw members of a rival gang, the Black Disciples.

It was late September on a busy South Side intersection, and now tensions were escalating, gang members who were there recalled.

There were glares, they said. Then words.

“You’re a rat,” a Black Disciple said to one of the Gangster Disciples who he believed had given the police information about him.

Things were about to blow.

It had been exactly 90 days since some of these same men had sat across from one another in an airy church hall to broker peace and confront a hard truth: The gang war they had inherited and were viciously continuing was helping to unravel parts of this city, where the levels of violence were reaching horrific new heights.

With 768 murders as of Tuesday, according to the Chicago Tribune, 2016 has been Chicago’s deadliest year since 1997. Toronto, which has a comparable population, has seen fewer than a tenth as many homicides this year, at 67.

Six people died over the Memorial Day long weekend, three days that saw 49 shootings involving 64 victims. One of the shooting survivors from that weekend was a Gangster Disciple known as Mexico, shot in his right leg on May 29 when tensions flared between the same factions that were about to square off in front of the store, New Food Inc.

An overwhelming majority of the 4,324 shooting victims this year were shot in gang-related crimes, the police say. What that means has become increasingly fuzzy, as the large, well-organized operations built around drug dealing have splintered, and are now little more than cliques or sets.

The New York Times spent several weeks this fall with gang members to get a better understanding of what it means to be in a gang. They were often days of boredom, punctuated by bursts of drama and bravado. Gang life means animated debates over whether the guys on the next block meant to insult you or not. It means worrying over how to make enough for your next meal or your next high. And it means mourning the loss of loved ones, retaliating in their honour, yet wanting the cycle to stop.

Ron, a 23-year-old Black Disciple who uses the nickname Kaos, and for safety reasons asked that his last name not be used, explained the relentless cycle of violence: I’ve already lost friends. If we are making money, I can ignore the urge to retaliate. “But if we’re sitting here bored, getting high and we got guns around, it ain’t nothing else to do,” he added.

Still, these are young men who defy easy caricature. They are the sales associates who help you find shoes at a sportswear store or factory workers next to you on the assembly line. They kiss their young children on the lips and cry when someone close to them dies.

And, yes, they do use and sell drugs, and sometimes lash out in inexplicable bursts of violence over disputes like a battle for a girl’s attention, or disrespectful words uttered on a rap video posted to YouTube.

Or, as was the case in front of the corner store in late September, over an insult hurled on a busy intersection.

There was supposed to be a mechanism to stop this from escalating. During the peace talks at Pastor Corey Brooks’ New Beginnings Church in June, the rival factions had brokered a truce. They had agreed to run their disputes up the ladder to gang elders, who would work to quash them.

But now things moved fast, said the two gang members who were there. After the insult, the Gangster Disciples left the block, but then returned, and the verbal jabbing continued. Then, the Gangster Disciples claim, the Black Disciple who had called one of them a rat reached into his pocket and pulled out his cellphone, pretending it was a gun. The Black Disciples denied that.

Whatever the truth, a Gangster Disciple whipped out a pistol and opened fire, witnesses said. The busy block scattered. And the Black Disciple with the phone was shot in his foot. The truce established in the church hall had been broken.

Kings of corners and blocks

After the shooting, dozens of Black Disciples gathered at their home base: the Parkway Garden Homes, a complex of brick midrise buildings stretching three blocks along South Martin Luther King Jr. Drive, built in the 1950s to house black middle-class families. Michelle Obama lived there as a toddler.

But over time, the middle-class families left, and mostly low-income families moved in. More than half the population lives in poverty in Parkway and the surrounding neighbourhood, which is 95 per cent black. An abandoned pharmacy sits on King Drive, along with cellphone stores and fast food shops that moved in when many businesses picked up and left.

Parkway earned a reputation as one of Chicago’s most violent areas. It was, however, considered a safe zone for the Black Disciples who controlled the complex — a faction known as O’Block, named after a fallen ally, Odee Perry.

Now they were debating how to respond to the shooting at New Food.

Some people wanted to respect the truce, in large part because it allowed them to make money by selling drugs in peace. That was why many had advocated for it in the first place.

Others, however, turned to the man who had been shot, Kaos recalled.

“We’re with whatever you’re with — however you feel about it because you got shot,” he recalled some people saying. “If you want to push, we’re going to push.”

Black gangs began sprouting in Chicago in earnest in the 1950s during a second wave of northward migration of black Southerners. The migrants came looking for opportunity, but were crammed into overcrowded, segregated pockets on the city’s South and West sides where industry and jobs were dwindling.

Conditions were ripe for what followed: Boys, with little supervision, money or education, formed cliques. They hung out socially, and got into fights and other petty trouble.

The rabble-rousing evolved into extortion of local businesses, much as it did with the existing white ethnic gangs and local mobsters. Then came the heroin and crack epidemics that turned gangs into lucrative drug-trafficking organizations that fought over territory. For a while, though, the gangs in Woodlawn also helped keep calm and avoid riots after the assassination of the Rev. Martin Luther King Jr. and helped with a federally funded job training program in the area.

But those highly organized operations have fizzled over the last 25 years as prosecutors swept up gang leaders, and the city demolished public housing projects, dispersing gang members primarily to minority neighbourhoods on the West and South Sides.

Now they were everywhere and nowhere — gangsters by name, but kings only of corners and blocks.

And instead of turf and money, they fought over personal slights.

Kaos was coy about how O’Block responded to the shots fired by the Jaro City member at New Food. Violence did, however, continue that week.

Two days after the New Food shooting, two Gangster Disciples were shot at night in a drive-by about a block from the store, but people on both sides said that particular shooting was unrelated to the feud.

A day later, the two sides clashed again near New Food, firing shots at each other. The mother of a Black Disciple was caught in the crossfire, shot in her left foot.

By late that afternoon, Sept. 22, alarm bells were going off at New Beginnings Church. Brooks huddled with some of the gang elders. The truce seemed to be falling apart.

Lavondale Glass, 43, a former Gangster Disciple who was helping to broker peace, saw the young men falling into the dangerous logic of revenge.

“This is what I don’t understand with the younger generation,” Glass, who goes by the name Big Dale, told Kaos one day. “How could you honour the dead and not the living?” Those who were killed are dead, he said. “Ain’t no bringing them back.”

Big Dale had lost his own father, Leon Holton, in 1996 — assassinated in a Gangster Disciple power struggle as federal agents were moving hard against many of the gang’s top lieutenants. His son, who is part of the Jaro City faction, was shot in the hand a few days before the truce was brokered.

But there often comes a time when the gang members lucky to make it past their 30s face the damage they have done and want to fix it. Big Dale had reached that point.

Brooks and the elders decided that Big Dale would gather the Gangster Disciples to discuss what was going on, while the Black Disciple old heads would do the same with their side. They would then hold a joint session to determine how to get the peace back on track.

But after the Black Disciples spent about an hour shouting at one another in a parking lot behind the church, the elders realized they first needed to resolve an internal rift. It appeared that some in the O’Block clique were jealous because, while they were broke, their allies from the 63rd Street faction seemed to be making money selling drugs, said a former Black Disciple who described the issue only on the condition of anonymity.

The attitude of some of the young men on O’Block was that if they couldn’t make money, then “can’t nobody get nothing,” the former Black Disciple said. “When they get bored, they do stupid stuff.”

Gangster life: boring, terrifying

Boredom is, indeed, a big part of gang life.

But boredom mixed with desperation can turn menacing.

And that was where several of Kaos’ gang allies found themselves on a chilly night in late October as they slipped on clear Guy Fawkes masks and set upon a man they saw walking by himself along King Drive. They were broke, and this is what they were going to do about it.

When Kaos was growing up, gang life seemed like anything but a thrifty, desperate existence. Living with his mother in the Robert Taylor Homes, a sprawling and notorious housing project just south of downtown, he saw the closets stuffed with plastic Aldi bags of cash, stashed by Gangster Disciples, he said.

He moved away when the projects were demolished, and stayed with his grandmother in Black Disciples territory. By his early teens, he was found to have an impulsive behaviour disorder, he said. He became deeply immersed in the Black Disciples after a friend was killed by a rival of the gang.

At around 13, he said, he faced his first serious charges: attempted murder, which landed him in juvenile jail. He was charged with three gun felonies as an adult, but earned a GED in prison, he said.

He spent two semesters in cooking school but dropped out in part because it was in rival gang territory and was dangerous, he said.

He has managed to make enough money selling drugs to pose as something of a high roller. Tall with blond dreadlocks often hidden beneath a safari hat, Kaos wears Balmain jeans that cost hundreds of dollars, a Versace belt and a glittering wristwatch.

But on this October day, his flashy trappings were mostly for show because he had gone several months without selling drugs, he said. Good product was hard to come by.

He hung out in an apartment he shared with a girlfriend, and some friends stopped by. They all lamented the same problem: They had no money.

For some, there was admittedly a lack of motivation to job-hunt. For others, criminal records got in the way. Kaos said he had been turned away by Wal-Mart, Walgreens, Footlocker and others. One in four adults in this neighbourhood has not graduated from high school, and the unemployment rate is 33 per cent, 2 ½ times the citywide rate.

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Even when Kaos landed a job, there were complications getting there. Riding public transportation can make gang members easy targets for rivals.

But the alternatives are tough, too: Kaos had recently gotten a job with a company baking pastries for international flights, but he quit after three days because he wouldn’t be paid until after his second week, he said, and he didn’t have gas money to get to work. And in a neighbourhood where people haggle over dollar bills, he did not have anyone to borrow money from.

As darkness fell, Kaos said he peeked out of the window and saw about 10 gang allies slipping on the Guy Fawkes masks.

A few minutes later, one knocked on his door, Kaos said. He and some of the younger gang members had tried to rob a man, he told Kaos. But the man pulled a pistol, shot one of them in the leg and ran off.

An ambulance carted away the wounded man. His friends lingered in the courtyard, laughing about the fiasco.

Inside, Kaos shook his head.

“I don’t know what they were thinking,” he said, injecting a curse word.

He later lamented, “It only takes one to push a crowd.”

Now there were fresh worries: The man they tried to rob could belong to a gang, meaning they may have incited a battle with an unknown clique, Kaos said. And if that guy wanted to retaliate, he had the element of surprise on his side because no one got a good look at his face.

Red hoodie on enemy turf

Retaliation is a universal worry of gang members. So it was in the rival Jaro City, which had been in a state of alert since the New Food shooting weeks earlier.

The clique worried that the war was about to flare again, said Antwine White, 24, a Gangster Disciple who is called Weedy. “You just get prepared for the worst,” he said. “They can walk over here. We can think it’s cool. They shoot.”

That defines day-to-day gang life in Chicago. The young men bound around with their chests out, but their heads are on constant swivels, eyeing everything around them.

It’s why the gang members here engage in their own sort of profiling: People with dreadlocks and hoodies, especially those they have never seen before, draw more scrutiny.

And so, weeks after the convenience store shooting, when peace seemed to have been restored, a passionate discussion about politics and revolution between Weedy and his gang allies broke up at the sight of an unfamiliar face: a man in a red hoodie.

“Steady walking back and forth on the corner, right here in front of Rothschild,” a fellow Gangster Disciple said, referring to a liquor store about 100 metres from where they were standing.

A couple of the Gangster Disciples hustled over to check him out. But Weedy hung back.

Here he was, caught in a middle ground of ambivalence. Am I in the gang or out? How can I leave when most of my friends are still in it? Or when I still need to rely on it to make a few dollars?

Weedy grew up on the block. His father was a prominent Gangster Disciple. His father’s friends would get a kick out of it whenever they reached for Weedy’s hand and he would mimic the gang handshake.

He relished the attention. But as he got older, he yearned for a deeper relationship with his father. There was no fatherly slap on the back or shoes promised to him for making the honour roll. His father, who Weedy said had a drinking problem, would arrange to pick him up from his mother’s house, but he would sit there until 2 a.m., waiting.

“Once I got immune to him lying, it was a wrap,” Weedy said. “My trust, that bond with him wasn’t there no more.”

So when he got into fights at school, when he needed information or wanted help solving problems, Weedy did not call his father. He turned to his friends on the block.

The streets became even more appealing after a popular Gangster Disciple, Jarvis Smith, 22, was killed 11 years ago, drawing everyone in the neighbourhood closer.

Weedy started selling drugs and gambling. He wasn’t a gunman himself, he said, but he would put up money to buy guns.

All seemed well until June 2, 2014, when he was headed to his job at a sportswear store downtown.

Weedy would take the elevated train, but the closest stop was near rival turf, so he used one farther away in the other direction. As he walked toward the stop, he felt a shock pulse through his body. He fell.

On the ground, he said, he looked over his shoulder and saw a man firing a gun about 20 metres away. Weedy had been shot twice before, but those were relatively minor injuries. This was serious.

“I thought he was going to run up, stand over me,” Weedy said. “I thought it was over.”

His son was then only about six months old and it pained him, he said, to think the boy would grow up without a father. But the shooter never rushed up for the kill.

After that, Weedy started thinking differently, he said. He resolved to reconcile with his father. He would recommit to leading his son in a better direction. And he told his friends not to seek revenge.

“I’m covered in the blood of Jesus,” he told them.

But leaving gang life is not simple. For one, just because you say you’re out of the gang doesn’t mean your rivals see it that way.

On that afternoon, while his friends marched over to see if the man in the red hoodie was a threat, Weedy hung back. His allies would learn that the young man was, indeed, a rival’s relative. But he was not doing anything threatening, so they let it go.

Weedy leaned on a black iron gate, looking on from afar.

“Even if it was an opp, he can go to the store,” Weedy said, using the slang term for a rival. “We go to their store. What’s the problem? You got to play fair.”

He has not fully extricated himself from gang life, and may never do so. But here he was, no stranger himself to gunplay, questioning not just the scene playing out before him, but his own life.

It was a delicate dance, Weedy said. Approach an opp aggressively and he might shoot you. Or you’re the one with the gun. “He talk crazy, you shoot him,” he said.

“You go to jail, you get killed. It’s either/or. For what?”