Charles Barber - Citizen Outlaw: One Mans Journey from Gangleader to Peacekeeper

William Outlaws first mug-shot, 1984.

New Haven Police Department.

W ILLIAM O UTLAW SAW, THROUGH THE FAINT GLOW OF THE STREETLIGHTS of Church Street South, a man approaching him. He would learn later that the name of this man was Sterling Williams. The man came closer to Outlaw, and Outlaw could see that this man, Sterling Williams, was stocky. To Outlaw, who was twenty at the time, the encroaching man appeared to be in his thirties.

Im here for Juneboy, Sterling Williams said. He spoke with a Jamaican accent. Juneboy, Williams middle name, was also his street name, and what everybody in New Haven called him. His full given name was William Juneboy Outlaw III.

Outlaw said nothing to the manhe just examined him furtherbut he felt for the revolver in the deep pocket of his cargo pants.

As Outlaw surveyed the interloper before him, it was one in the morning and unseasonably warm in New Haven, Indian summer. Outlaw was sitting on the hood of an abandoned car, an old Ford, holding court, as usual. He was surrounded by five young men, teenagers mainly, and all members of his gang, which was called the Jungle Boys. The young men circled around Outlaw wore Nike and Adidas sneakers, camouflage pants and green T-shirts, for green was the official color of the Jungle Boys, and the more prosperous among them wore gold chains. They stood on the edge of a run-down and densely packed housing project known as the Jungle, which Outlaw had selected three years earlier as the base of his criminal operations, the perfect place from which to deal cocaine. As Outlaw spoke, his gold-plated front teeth flashed under the streetlights. One tooth was engraved with the letter J, and the other with the letter B.

As he sat on the hood of the abandoned car, the various members of the Jungle Boys listened to him attentively. Outlaw was their indisputable leader, renowned equally for his loyalty to them and his viciousness to rivals. For most of the members of the gang, which numbered about forty, Outlaw had represented their meal ticket out of poverty, which was pervasive through large swaths of the city, especially among young black men. Virtually all of New Havens factories had long since closed, and being selected by Outlaw for the gang was for some of them like winning an unexpected lottery. There was something irrepressible about Outlaw, a quality of complete self-possession: when he talked to you, it was as if no one else in the world even existed.

As Sterling Williams stood there, and Outlaw gripped his gun wondering what he would do next, the night air was almost misty. The occasional car drove by on Church Street South and there was the faint rumble of traffic from Interstate 95, a quarter mile away.

Outlaw and the Jungle Boys had been expecting a fight all day. Outlaw had heard earlier that day that Sterling Williams or someone like him might be visitingthere had been rumors flying around the Jungle that there might be trouble coming from New York, in the form of Jamaican gangsters looking to shoot, kill, and torture, whatever was necessary, to force themselves into new territory. Within the last year, the Jamaicans had taken over most of the drug trade in Bridgeport, a city twenty miles to the west. A few months earlier, in an opening salvo in their bid to dominate New Haven, they had killed a childhood friend of Outlaws, a lone-wolf drug dealer. The Jamaicans had shot him execution-style, five bullets to the head, up at East Rock Park, at the top of a cliff that gloomily overlooks the entire city. The killing was interpreted by gangs in New Haven as largely symbolic, intended to send a message to the city that the Jamaicans were ready to take over.

Earlier that day, one of the Jungle Boys had been playing rap music, loudly, on a boom box, while proceeding down Liberty Street a few blocks from the Jungle. A young Jamaican with dreadlocks had accosted the member of the Jungle Boys and told him to turn off the music. The Jungle Boy, trained to be on the offensive, had taken a pistol out of his pocket and smacked the Jamaican with the butt of the gun, repeatedly, until he crumpled to the pavement. Blood already beginning to drip from his face, the Jamaican had uttered, Were going to fuck all of you guys up. Were going to kill Juneboy.

This encounter prompted a chain reaction of events, conducted with the high efficiency with which the Jungle Boys, now three years in operation, conducted their business. Outlaw was paged by his second in command and protg, Ricky, who helped run the gang while Outlaw was out of town. Outlaw was in Harlem that day, ostensibly on business, but also pleasure. He was procuring cocaine, the lifeblood of the Jungle Boys, kilos of it from the Albanian intermediaries with whom Outlaw had been buying for years. But hed also been partying there, on 125th Street in particular, taking advantage of the clubs, and women, and clothing boutiques that he had begun to frequent as the Jungle Boys had grown in power and resources. Ricky told Outlaw to come back to New Haven immediately. They needed his help. Driving one of the forty cars that the Jungle Boys now maintained back home, he had pulled up to the Jungle fifteen minutes before Sterling Williams appeared.

Now, Sterling Williams stepped even closer toward the group of Outlaws boys and repeated, I am looking for Juneboy.

Outlaw was on alert, but he wasnt particularly anxious. He wasnt generally an anxious person. But he gripped the handle of the gun in his pocket harder.

One of his underlings, a slim eighteen-year-old looking to work his way up in the gang, said, Im Juneboy.

Outlaw liked thatit gave him cover. Thats what he had trained his guys to do. And it allowed Outlaw to get closer to Sterling Williams without Williams being aware. Outlaw moved within five feet of Sterling Williams, so that he could see his dark face through the night shadows. Williams was wearing a baseball cap backward and had long dreadlocks.

Sterling Williams said, in a lilting Jamaican accent, and to the wrong guy, Im going to fuck you up. I am going to take over your gang. Im from New York and Im going to kill all of you, and Im going to kill Juneboy.

Outlaw was shocked at the mans sheer and utter recklessness. He could not believe his aggressiveness, nor his foolhardiness. No one ever addressed him, or a person presumed to be him, like that, ever. The Jungle Boys did the terrorizing, not the other way around. They were by far the biggest gang in New Haven, and the only one to operate in three neighborhoods. Outlaws crews were organized by shifts, job descriptions, and pay scales. Last year hed made something like a million dollars, although he wasnt really counting.

Outlaw figured that, in order to be so crazily reckless, this man Sterling Williams must have some serious backup. Outlaw didnt know much about the Jamaican gangsters coming out of New York, but he did know that they called themselves the Shower Posse, and that they were especially vicious, even by a gangs standards. They performed ritual killings, tortured people, killed your family if they couldnt get you. He knew that they were based in Bedford-Stuyvesant and he knew that two splinter groups of the Shower Posse, calling themselves the Rats and the Cats, had taken over Bridgeport. Outlaw peered through the darkness to the small apartment buildings and ramshackle ranch houses and parked cars on the other side of the street. He expected to see more guys, waiting to attack. But all was quiet. There didnt seem to be anybody else.