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Street Smart
As Boston became overwhelmed by gangs, probation officer Bill Stewart '73 decided the killing had to stop
by C.W. Wolff
Photography by Perry Smith


"JUST SO YOU KNOW—I PUT PEOPLE IN JAIL FOR A LIVING," William Stewart III '73 used to tell the captains of opposing ice hockey teams before the first buzzer. "So a 10-minute misconduct or throwing you out of the game is not a big problem for me."

It's an up-front style Stewart no longer needs for refereeing Division I college and high school hockey; he hung up the whistle in 2004. But it's a style that still serves him well as a Boston probation officer whose approach to youth violence has become a national model.

When Stewart started work as a Dorchester District Court youth probation officer on his 27th birthday in 1977, he wore a three-piece Brooks Brother suit and a striped tie. In those days, the crime of choice among young Bostonians was nonviolent car theft. His work hours were 8:30 to 4:30, and his clients were cooperative and eager to meet the terms of their probation. "Everything with them was always 'fine,'" he recalls. Stewart transferred to working with adults for several years, and when he returned to the youth division in 1988, he knew everything definitely was not "fine."

"Crack cocaine had hit the streets, and I saw a look on the faces of the kids that frightened me. I was talking to the side of their heads," he says. Many of his clients bore the scars of gunshot or knife wounds. "With the drug dealing came the cash and with the cash came the guns to protect profit and turf. With the turf came the gangs and with the gangs came the violence."

The bloodshed escalated. In five years—from 1990 to 1994—there were 540 homicides in Boston. Of the victims, 260 were under age 24, and 66 were under age 17. Stewart knew 68 personally. "I can still remember all their names," he says.

"There's something abhorrently wrong about a kid lying in the street with a blanket over him and his life flowing into the gutter. It just doesn't happen in Wellesley. It doesn't happen in Durham. And it doesn't have to happen here," Stewart says with quiet intensity, recalling the day in 1990 when he first saw one of his clients dead on the street. Freddy B., whose street name was P-nut, had been shot at 3 in the afternoon just three blocks from the courthouse after spray-painting his name on another Dorchester gang's turf.

Even when Stewart was growing up in Dorchester, the streets were rough. At age 12, he stood his ground when an older kid tried to take away his new hockey stick. He was stabbed in the stomach and nearly died. But that kind of violence was not common, and Stewart recalls a sense of community, with kids laughing on playgrounds and adults watching out for their neighbors.

By the 1990s, however, the sidewalks and playgrounds belonged to gangs, and parents were putting their children to bed in the bathtub to avoid stray bullets. Probation officers stayed in the fortress of the court building, insisting clients come to them instead of visiting them in their homes. The only time they spent on the streets was the walk from the parking lot to work and back.

RIDING THE BLUE LIGHTS

Stewart knew things had to change. When P-nut's mother accused him at the funeral of letting her son be killed, Stewart denied it, saying he warned him to leave his gang. But privately he took the litmus test his father always recommended: "Am I doing the best I can do?" He suspected he was not. So he and another probation officer, Richard Skinner, hit the streets.

For starters, Stewart began wearing jeans and putting his baseball cap on backwards. He learned some of the popular, hip-hop style hand motions, as well as street talk: "Bustin' fresh" or "stylin'" for looking well dressed and well groomed; "blue lights" for police car, although more recently "5-O;" "Das Coolio" for that's cool; "tag," meaning to spray paint one's street name; "S'up?" for what's up.

He and Skinner memorized kids' street names and gang affiliations. They tried to become a presence on the street—sometimes pulling up to a group of young men to ask for directions to the state prison, or spray painting Xs over the tag names of gang members who had been killed or incarcerated. "Do you want to be next?" Stewart would challenge any youth who might be watching.


"I wanted them to think I was a little crazy," says Stewart. Just being a white guy out on the streets of Dorchester in those days was one indication of crazy. Being a wisecracker probation officer just added to the mystique. Once, while in Kansas on a speaking trip, Stewart detoured to visit Leavenworth Penitentiary just to say "Good morning" to an inmate he had helped put there. News of his visit was on Dorchester streets by the next morning.

But to really be effective—to get kids to open up to him and trust him—Stewart needed to do more than make himself a legend on the street. "We have to see what that kid sees when he opens his eyes in the morning and what he sees at night," he explains. "We have to get into his world." That was part of Stewart's motivation for requesting that he and his partner, Skinner, be allowed to ride with police at night to check on their clients on the street and in their homes.

Initially, Stewart's idea was not an easy sell to police officers, who viewed probation officers more as caseworkers than as law enforcers. "Whenever you have a non-police person riding around in the car with you, you're apprehensive," says Robert Fretalia, the first police officer to agree to take Stewart along. It helped that Stewart had refereed Fretalia's high school football games. ("He needed glasses, but he was fair," says Fretalia.) Another factor was Stewart's discovery, during a summer vacation spent reading law books, that in some circumstances probation officers have greater enforcement powers than police officers. Without a warrant they can search people on probation, their homes or their cars, and can arrest them—all on reasonable suspicion.

Stewart and Skinner rode with Fretalia and his partner for the first time in November 1992. Within 15 minutes they were called to a shooting. The victim, who died, was one of Skinner's clients. In the crowd at the crime scene, Stewart recognized more than 30 kids in violation of their probation curfew. The kids in turn were shocked to see a probation officer after dark. But they talked to him, providing information that led to the arrest of the murderer.

The police dubbed the program Operation Nite Lite, and it became a key element to the Boston Strategy for Preventing Youth Violence. The guidelines for night visits to clients' homes were simple: The police were there as escorts for the probation officers, and everyone would be polite. But Stewart believes in being polite and honest. "I remember going to a house in 1994 and the mother said, 'I don't like white people coming to my house,'" Stewart recalls. "I told her I understood, but there were two reasons I was there. One was her son was on probation; if he weren't, I wouldn't have been there. The second reason was that I knew my son was safe and I wanted hers to be safe too."

"I told her, 'I'd prefer to see him at home with you than in jail. But I'd rather see him in jail than dead. When he went out, did he say, 'Good night, mom, I love you'? Well, tomorrow morning when he's in my office at 9 a.m. that's the first thing I'm going to work on. I'm going to make sure he says good night to his mom. OK? Have a nice night.'"

Stewart often goes into the bedroom of a curfew-violating client, makes his bed and leaves a lifesaver mint on the pillow with a note saying to come see him in the morning. He frequently rummages through the client's drawers or looks under the bed. Once, using as reasonable suspicion a display of gang colors on the wall, he searched a client's bedroom and found $5,000 in cash, 250 rocks of crack and an AK-47 assault rifle. The young man got seven to nine years.

But he's just as likely to chat with a client's grandmother or teach a teenage father how to burp his baby. And he doesn't believe his job ends when a kid is no longer on probation. One teen had gone through five probation officers by the time Stewart met him. With Stewart's encouragement he graduated from high school. He wanted to join the Army but was rejected because of his juvenile offenses. Stewart intervened. "Last I heard from him," Stewart says, "he sent me a picture of himself on duty in Germany."

A SILVER BULLET

While the police quickly became fans of Nite Lite, it was not widely accepted by other probation officers. Some accused Stewart of hounding his clients as well as risking his life. "We'll come to your funeral," they'd tell Stewart, who has been chased by a pit bull and threatened by a knife-wielding man who insisted Jehovah wanted him to kill a white man. He frequently wears a bulletproof vest for the night rides.

In 1997, however, President Clinton and Attorney General Janet Reno visited Boston and praised the program. In addition, Nite Lite received awards and extensive media coverage, including a 2000 cover story in Newsweek called "16 Silver Bullets: Smart Ideas to Fix the World." The program was also featured in The New York Times and on ABC Nightly News and PBS.

Nite Lite was institutionalized in 1998 and written into the contracts of all Massachusetts probation officers, who are now expected to spend 20 percent of their time in the community with police officers during nontraditional hours, before 8:30 a.m. or after 4:30 p.m.

Besides Nite Lite, Stewart became increasingly involved in other efforts to stymie youth violence. In April 1996, for instance, after two gang-related homicides, he suggested a forum to try to stop the expected spiral of retaliatory shootings. Working together, probation and police officers brought into one room all the members of both gangs and told them, according to Stewart, "Cut the violence. We're tired of the violence. Put your guns down. If not, three things are going to happen: You will be trailed, you will be nailed and you will be jailed."

Stewart helped carry out that threat. "We had undercover drug buys, strict enforcement of terms of probation, enforcement of jaywalking laws, enforcement of the 'breathing-without-a-brain' law, whatever we needed. I told them, 'I'm going to go into your bedroom and I'm going to flip your mattress and the sheets better be clean. I'm going to check your fingers, I'm going to urine-test you." Within six weeks, 23 gang members were arrested. The idea, Stewart says, was to "disrupt the criminal structure of the gang to lessen community fear and improve life in the targeted area." And, he says, it worked.

FUN WITH FELONS

Stewart takes MASH's Hawkeye as his role model and says that humor has saved his mental health. He calls it "fun with felons." He will say to a kid in a holding cell, "Don't go away—I'll be right back." Once, while he was watching a street where crack was being dealt, he saw a blond teenager driving a beat-up BMW slowly down the block. "I ran the plate and found out the kid was from the Cape," he says. "So I phoned and said, 'Mrs. so-and-so? This is the Lyon Street Crime Watch in Dorchester and I'm calling just to let you know your BMW with a blond male was on Lyon Street today, apparently for a drug transaction. We have enough problems up here with the kids who live here—we don't need anyone from Falmouth!'"

He enjoys shifting roles—attending a celebrity wine-and-cheese book signing one night and cruising the streets of Dorchester in a police car the next. He's worked as a bouncer in a Boston night club and also spent five summers as an assistant to the golf professional at the Hyannisport Club. "I can say 'terrific' without moving my mouth," he claims.

More recently, he has been hobnobbing in Beverley Hills, talking about his idea for a TV series that he summarizes as, "Kids are dying. Probation officer goes out on the streets. Kids aren't dying." Stewart, a dedicated movie fan, shared his idea with Howard Baldwin, former owner of the Hartford Whalers and the Pittsburg Penguins ice hockey teams and now a movie producer. Baldwin offered him a contract and is shopping for a network.

BRUSH YOUR TEETH

On a warm night in October, Stewart rides in the back of an unmarked car with three Mattapan officers. Two of them are wearing shorts. The bulging bulletproof vests under their T-shirts somehow make their bare knees look especially vulnerable. All of them watch the street but keep an ear tuned to the Red Sox game on the radio.

A laptop propped between the car's front seats gives them access to a database, letting them quickly run license plates and check the criminal status of anyone they might encounter.

It's after 9 p.m. and Stewart has been at work since 8 a.m. He is currently assigned to domestic violence, but since Nite Lite is now part of every probation officer's job, he helps out from time to time and tonight he has the names and addresses of three youths on probation he plans to visit.

Before going to the clients' apartments, they cruise the neighborhood, observing who is hanging on what corners, and looking for a fellow named Smoke. The young officer behind the wheel must have learned to drive in Boston. He turns corners from the wrong lanes, never stops at stop signs, makes U-turns wherever he wants and backs up fast. They glide to the curb next to Smoke and two other men.

"Hey, s'up?" calls Stewart.

"Nothin'. S'up you?" Smoke answers, rolling back on his heels and smiling. One of his friends takes a couple of steps backward and watches. He's not smiling. The third man continues walking, but is brought back to the little gathering by one of the officers.

Stewart tells Smoke he really should brush his teeth, which is his way of saying he can smell beer on his breath. Smoke gives up his brown paper bag and the open quart of Heineken it holds. He also gives up a small quantity of marijuana that Stewart later throws out the window of the police car. Everything is cordial and routine, although everyone knows there could have been a bust. "Now Smoke owes us," says Stewart when they're back in the car.

No one is home at the curfew check: a dark triple-decker flat. At the next stop, a woman who answers the door downstairs says the family they are looking for has moved, and, no, she doesn't know where they went.

At the third apartment, a shirtless man comes to the door. He's wearing a belt with a three-inch, rhinestone-dollar-sign belt buckle. The belt has no relation to the jeans that ride low on the man's hips. Stewart asks him how it's goin,' checks his fingers for marijuana stains and bids him a good night.

The police bring Stewart back to his own car, and he heads off to one of his favorite restaurants, where he talks on the street corner for 20 minutes with the restaurant owner and a couple of other friends before eating dinner. He leaves the restaurant at 11 p.m. He'll be back at work at 8 the next morning.



KEEPING KIDS ALIVE AND NEIGHBORHOODS SAFE

One of the main reasons for the success of the "Boston Strategy," a collection of programs designed to reduce youth violence created in the 1990s, is that it built collaboration among probation officers, police, judges, street workers and religious leaders. Eventually, teachers, business leaders, academics and politicians also were engaged in the strategy. At its core was a goal to reestablish safe neighborhoods, rather than focus on offenders.

The strategy's success can be documented by a sharp and steady decline in Boston homicides—from 152 in 1990, including 16 under age 17, to 98 in 1995, with nine victims under age 17, and no youth deaths among the 43 homicides in 1997. There's been an increase in homicide rates in Boston in the last few years—61 in 2004, including seven under the age of 17, and 75 in 2005, including nine who were 17 or younger.

Stewart attributes the rise in street homicides among youth in the past couple of years to several factors: increased availability of guns; the coming of age of children with problems connected to their parents' crack use; the lack of fathers in many homes; the return to the streets of prison-smart men Stewart helped to send to jail; and a change in Washington, D.C. The year "2000 was a benchmark," he says. "The Democrats left office, the Republicans came in and federal programs started to slide, then the kids, entitlement programs, started to slide and so did the communities. It's a cyclical thing, in my opinion."

But he believes the Boston Strategy, especially Nite Light, has worked and can continue to work. He cites complaints filed concerning people on probation—12,000 in 1990 down to 9,000 in 2000.

A number of cities are using the strategy as a model. Stewart alone has talked about the strategy with more than 60 groups around the nation. Posted from the ceiling to the floor on one wall in his small office in the Dorchester District Court building are postcards from every place he has spoken. "I like to think there is at least one kid still alive in each of those cities because of Nite Lite," he says.

For a description of the Boston strategy, see http://ojjdp.ncjrs.org/pubs/gun_violence/profile02.html.

C.W. Wolff is a freelance writer and editor who lives in Kittery, Maine.

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