The StreetSafe Question

What's the best way to turn around a young street thug? According to a revolutionary social program being revived in Boston's roughest neighborhoods, the answer just might be: with a reformed one.


Photographs by Christopher Churchill

Vito Gray talks about the day he almost killed a man in a voice not much above a whisper. He’s usually more authoritative than this: From the Timberland boots he favors to his black, shaved head and broad, imposing physique, Vito announces his presence—or rather, his presence announces him—with every languid step he takes. This proclamation extends, naturally, to his voice. It’s normally deeper than most men’s, and paced by a cadence that’s never hurried, because it has never needed to be. For most of Vito’s life, people made sure to listen to what he had to say.

But now, as he sits in an idling car on a rainy Saturday afternoon, overlooking the grassy common area of the Mission Hill projects in Roxbury, and recalls the drug empire he once ran here, Vito’s voice goes soft and loses its luster, especially when he’s asked about Victor Woods. His eyes narrow at the mention. “Who told you about that?” he says, as if he’s been wounded. The Globe ran the briefest of news briefs on it in 1991. The paper said that Vito was only 21 when he stabbed Woods, then 30.

The words come painfully slow now. “Yeah,” he says. Woods was a “dealer-slash-user” but wasn’t dealing for Vito, he says. “He had actually stolen one of the stashes…he stole, so”—and here the words collapse into a nearly inaudible drone—”there’s a penalty that has to be paid for that.”

He goes on. “Because if we don’t straighten it out, then, you know, then once he go around telling people he done took the dope, look at what they can do.” By which he means, Look at what can be done to Vito’s Mission Hill projects. “So we let it be known that we not going to tolerate that. Not stealing from us no way.” (Woods couldn’t be reached for comment. A Boston Police Department spokeswoman says that Woods’s name is unfamiliar to cops who tracked the drug scene in the early ’90s. But, she stresses, that doesn’t mean Woods was unfamiliar with the drug game itself.)

Vito isn’t angry recalling any of this. His tone never rises and his eyes look only to the soggy common area beyond the driver’s-side window. He feels terrible about it all. Not just terrible for Victor Woods, who lived. Or for himself, who did 10 years in state prison. He feels bad for the Mission Hill projects. What happens here now, among the latest generation—Vito Gray, 39, helped cause that. “Them seeing me get money. Them seeing me doing things,” Vito says. “They like the lifestyle.”

Atonement takes many forms, though. For Vito it came from the church, but also from a statistic buried in a 2008 report from Harvard’s Kennedy School of Government. The report said that as much as 60 percent of today’s crime in Boston is caused by one percent of the population. This revelation spurred the traditionally circumspect Boston Foundation to find a way to reach these one-percenters, many of whom are between the ages of 16 and 24. The result: a weeks-old outreach program of (legitimate) job training and (quite real) cautionary tales, staffed by men who know the streets because they are often of them. This is how Vito Gray became a Boston Foundation “street worker,” a member of the most revolutionary social-welfare outfit in the country.

The program is revolutionary not just for the means by which it attempts to succeed, but also for acknowledging the unintended consequences of the city’s prior success. The Boston Miracle of the 1990s did many things: organized the clergy, cops, and social services as never before; convicted gang leaders and drug lords like Vito to long sentences; and gave the city’s youths an 18-month—18-month—reprieve from a single murder, for which those involved with the Miracle received national funding and international fame. But the Boston Miracle also wiped out the hierarchies within the city’s street gangs. The kids who were left had no one to teach them the streets’ code of ethics: namely, when to shoot, and whom. More than a decade later, violence is once again on the rise, but the shootings and murders this time are often—if the word can be used in such a context—senseless, over personal beefs and misconstrued slights, not turf battles or mishandled drug deals, as was the case in Vito’s day. (“If it wasn’t about dollars, it didn’t make no sense,” he is fond of saying.) Street workers like Vito—men patrolling the streets they once ran—are providing a structure, a hierarchy of sorts, for today’s kids. It’s just that, this time, Vito and guys like him are teaching the kids while helping the other side of the law.


He looks good, in his faintly pinstriped suit and purple and pink tie, the stripes accentuating his squat, square build, as if he were a boxer turned promoter. This is graduation day for Robert Lewis Jr.’s first class of street workers—officially the “StreetSafe Boston street workers”—and Lewis is a few minutes late to leave his office at the Boston Foundation, on Arlington Street. He steps into his Acura with Kate Guedj, the foundation’s VP for philanthropic and donor services, and says he’ll take some shortcuts through the South End.

On a one-way avenue behind the drab Villa Victoria housing project, Lewis stops the car short. He pulls over to the left-side curb, hard against a chainlink fence and a playground of little more than concrete and loitering Hispanic teens. “Those are some of the Villa Boys,” Lewis says. There are three of them, all oversize white T-shirts, baggy jeans, and suspicious stares. One is wearing a red bandana. Lewis points. “See the one in the red? He’s probably 5-5, 5-6, 130 pounds?” Lewis says, getting agitated. “But he’s the shooter! He’ll blow your head off. I mean he’ll literally blow your head off!” He gazes for a moment more.

Photograph by Christopher Churchill

The point, Lewis says, pulling the car away and now a bit more controlled, is to disregard the notion of the hit man as menacing brute. “That’s Hollywood stuff,” he says. In the real world, in particular in Boston, it doesn’t take physical strength to carry a gun. Sometimes it doesn’t require proof that you’re 18.

It’s a good bit of analysis, later echoed by service workers and cops. But the real point of this trip through Villa Victoria is one Lewis doesn’t mention: Here is a man who may work for an august foundation and, yes, may very well wear nice suits, but look at how streetwise he remains, enough to know which threatening teenager on a South End playground is the troublesome one. As Guedj would later say, “Robert’s strength is his ability to live in both worlds.” He drew on that strength when conceiving the foundation’s street-worker program.

Lewis grew up in East Boston in the 1960s and 1970s. His mother had six kids by the age of 23. His father was an abusive drunk. Lewis himself found little comfort outside the home: His was the first black family to move into the Maverick Street housing projects in Eastie. Lewis knew the hatred of the busing era. One night in 1976, when he was a sophomore in high school, he watched as his friend, a white kid, approached Lewis’s home with a bottle in his hand, lit the string on the end, and threw the Molotov cocktail through the window. The Lewises’ apartment burned down.

They moved to the South End—into Villa Victoria, in fact—where Lewis vowed, “Whatever I do in my life, I’m going to do things that bring people together.” He was an exceptional football player, which got him into UMass but didn’t get him a degree. After opening the city’s first black-owned health club in 1986 in Jamaica Plain, Lewis came to the attention of Mayor Tom Menino, who recruited him to work in many social-service capacities—his real passion—from the early 1990s to 2007. These jobs required an intimacy with the streets. He learned the most by asking the least of kids, it seemed, by hanging out with them until they were comfortable enough to share their secrets.

Lewis became widely known in philanthropic circles, and was offered a job with the one of the city’s oldest philanthropies, the Boston Foundation, because, in the words of Boston Foundation president and CEO Paul Grogan, “I just wasn’t satisfied that the nerve endings of the foundation extended as far and as deep as they needed to.”

Grogan is, as Lewis would say, an interesting cat. Before Grogan took over in 2001, the Boston Foundation wrote respectable checks for respectable charities, its genteel reserve as Brahmin then as it was at its founding in 1915. Grogan changed that. He demanded the foundation play a more active role in the city. For instance, he and the foundation produced biennial reports called “Boston Indicators” that so directly challenged the city to do more that Menino worried Grogan would run for mayor. (That was never the plan.) Long before it was fashionable for liberals, the foundation argued for charter schools, on the belief that the status quo of struggling public schools would never improve fast enough for Boston’s inner-city kids. But only after Lewis came on in 2007, as vice president of programs, did Grogan and the Boston Foundation fulfill their baldest ambitions.

Lewis knew that reducing violent crime in Boston would mean more than locking up the kids that fired the guns. And when the Kennedy School of Government produced the report in the spring of 2008 saying that one percent of the public caused almost 60 percent of Boston’s crime, it confirmed the need for Lewis and Grogan to create a program that urges precisely these troubled youths to seek a less destructive path. The best way to do that, Lewis argued, was through credible messengers. Some of them would have to have rap sheets as long as the kids’ own. All of them would need to be on the streets when the kids were: after dark. This meant that the messengers had to be convincing—and savvy enough to protect themselves. After all, the kids might respect their elders’ past, but these same youths had never been restrained by any established hierarchy of the streets.

As the job qualifications mounted, it became clear that Lewis’s expertise would have to inform the hiring process. In other words, for arguably the first time in its history, the Boston Foundation would need to do more than cut a check and wish the institutions closer to the action the best of luck. To do this so-called street-worker program right, the Boston Foundation would have to insert itself into a far more public role. It would have to become less a foundation and more a very wealthy community center. It would have to put its mouth where its money had long been: on the front lines.

Grogan loved that. And more than a year later, on a sunny evening this past June, Lewis attends the graduation ceremony in a city building in the South End for the inaugural class of Boston Foundation–funded street workers, 13 in all. Despite his brief stop at the Villa Victoria housing projects, Lewis isn’t that late. The street workers—some of them ex-cons like Vito Gray; many of them having spent years as community activists; a couple joking how suave Lewis’s suit looks—have just completed 50 hours of social-service training, and they celebrate by forming a circle and describing what this work means to them. When it is Lewis’s turn to speak, he says, “I’m going to be honest. We’re better than an all-star team here.”

Lewis would know. Twenty years earlier he created a cruder street-worker program that was an integral part of the Boston Miracle.


To understand the miracle, you must first understand why the city needed one. And to understand that, you need to know a bit more about Boston’s gang culture.

We’ve never had well-organized gangs, at least not on the level of the Bloods, Crips, and Latin Kings—national syndicates with a clear structure of power. Those gangs have tried to recruit here, but they’ve had only limited success. Boston remains a provincial town. It’s so provincial, in fact, that gangs here are organized not by city, or region, or even by neighborhood, but by street: Intervale in Roxbury; Corbet in Dorchester. At their most inclusive, gangs align themselves around the projects in which their members grew up: Mission Hill in Roxbury; Academy on the border of J.P. and Roxbury. Theories abound for this tribalism, but the best explanation may be that Boston is a compact city—48 square miles—with most of the violent crime occurring in a roughly 1½-mile radius that stretches from parts of the South End to parts of Mattapan and has as its main thoroughfare Blue Hill Avenue. In short, there’s not much ground for anyone to claim, so you claim what you can, even if it’s only the street you live on.