Street Smart
As Boston became overwhelmed by gangs, probation officer Bill Stewart '73 decided the killing had to stop

Bill Stewart

"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.

TOUR OF DUTY: Bill Stewart '73, above right, rides with Sgt. Mike Kearn.

"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.


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.

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