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.

By Paul Kix | Boston Magazine |

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.

There was gang activity before the 1980s, but gangs in Boston didn’t really organize themselves until crack hit the streets. Then it was hell with the lid off. Turf wars, drug-fueled shootings—by 1990, the murder rate had hit an all-time high in Boston, 152 homicides. Paul Evans, who would later become the city’s police commissioner during the Miracle, wondered aloud, in his John Lindsay moment, if the city would remain livable.

Vito Gray knew those years well. He grew up in Mission Hill in the late 1970s and early 1980s, where his father dealt drugs for a living. His older brother and sister stayed away from the game, but Vito didn’t. He was in and out of the state’s Department of Youth Services from age 13 on for dealing. At first it was weed; by the end of the 1980s, as he became a man, it was heroin, crack, whatever the marketplace wanted. Only by then he wasn’t dealing much himself. He was “one of the bosses,” he says. He oversaw supply. He gauged demand. He collected the money. He says he didn’t order hits, but Robert Lewis Jr., who knew Vito then, says he was feared on the streets. “He was an asshole,” Lewis says. For the attempted murder of Victor Woods, Vito served six years in prison, beginning in 1991.

Lewis created a street-worker program while working in the mayor’s office a year earlier, in response to the record-high murder rate. Forty mostly minority men and women tried to reach gang members wherever they might be and convince them to stop, or at least offer them reasons to. The program wasn’t as focused—in recruitment, training, or execution—as today’s effort. But it was a step up from the existing neighborhood watch groups, and can be considered among the first initiatives of the Boston Miracle.

It is, alas, tough to track the chronology of that thing. So many people and ideas came together during the Miracle, melding into a unified front of We’re Not Going to Take This Anymore, that it’s hard to say this program led to that reduction in crime. But it’s worth recalling a few key moments.

In May 1992, Mattapan’s Morning Star Baptist Church held a funeral service for Robert Odom, who had been killed by members of a neighboring gang. Hooded affiliates from another gang, the Vamp Hill Kings, burst through the doors mid-service and opened fire on the mourners, stabbing one teen nine times. Out of that horrific day came the famed Ten Point Coalition, a grassroots effort led by prominent black clergymen to, among other things, convince gang members to find legitimate work.

At the same time, Boston law enforcement was collaborating. First with Operation Night Light, in which parole officers visited parolees at night, in their homes, to ensure no court-imposed curfew was broken. And next with Operation Ceasefire, in which cops, clergy, lawyers, and academics devised a plan that threatened gang leaders from targeted areas—the 1990s’ one-percenters—with long federal sentences for any mishap. Freddie Cardoza became the unfortunate poster child of Operation Ceasefire. A nasty gang leader, he was arrested in 1995 for possessing a single bullet, which he flipped in the air to taunt some nearby cops. Many prior federal convictions allowed the U.S. Attorney’s Office to prosecute with impunity. Cardoza got 19 years in a Kansas federal prison essentially for flipping that bullet, a message not lost on other gang heads.

This concerted effort by Boston’s civic leaders to oust its criminal leaders had a profound effect on the city. By 1999, the murder rate hit a historic low: 31 homicides. Nationally, the 1990s saw a dip in crime, but Boston’s decrease was six times the national average. During an 18-month stretch between 1996 and 1998, no child under 18 was killed in Boston. That’s still seen by law enforcement officials as miraculous.


So what happened? September 11, for one. National funding for domestic crime prevention was transferred to the war on terror. More than that, though, violent crime in Boston began to edge up—from 40 homicides in 2000 to 75 five years later—because of “egos,” says Chris Byner, a longtime community worker for the city now overseeing the day-to-day operations of the street-worker program. “Egos got in the way. People started to think they were bigger than the group.” Eugene Rivers split from the other ministers and formed the National Ten Point Coalition. Police Commissioner Evans took a prestigious law enforcement job in England. Moreover, gang unit cops got promoted. Government attorneys received better pay and more-complex cases. Byner himself went from a street worker to the program’s supervisor. There’s little shame in this—commendations follow exemplary achievement, after all—but the Miracle workers’ promotions, Byner says, created a vacuum of knowledge similar to that which gang members faced after Operation Ceasefire. “The people who invested in this, they’re gone,” he says.

Lastly, and most important, those same leaders of the 1990s failed to heed the demographics. A report during the halcyon Miracle days, from Northeastern criminologist James Alan Fox, noted a coming population boom of minority teenagers. When Operation Ceasefire ended in 2000, and with it, in hindsight, the Miracle, those kids were the new foot soldiers of their street gangs. Only now, they didn’t have elders to tell them the streets’ code of ethics; those guys were often locked up. Within this vacuum the kids made their own rules and fired their petty jealousies at each other, increasingly in broad daylight, and around people of legitimate means.

The game changed. Now you only had to demand respect, instead of demanding fat profits and then respect. That’s a key distinction.

Because what’s happening today is tough to police. Yes, the murders are down from the pre-Miracle days—63 last year, according to police department figures, a murder rate two and a half times lower than that of Baltimore, whose population roughly mirrors Boston’s. But the brazenness and seeming randomness of many of today’s shootings are in some ways scarier than in the 1980s. Soheil Turner, for instance, a 15-year-old from Orchard Park in Roxbury who was gunned down at 7:20 a.m. on May 7 while waiting for the bus to school—his alleged killer reportedly didn’t like guys from Orchard Park and so didn’t think much of taking Turner’s life. He went to school that day.

“The rules are different,” says Boston Police Superintendent Paul Joyce, who worked in the 1990s in the department’s gang unit. “You can have two gang members from rival gangs, they’re not fighting over the gang issues. They’re fighting over personal issues. These personal issues can be so broadly defined…that it is very hard to police.” This decade has been marked, then, by an almost granular approach to investigations: looking at the individuals’ past within these gangs, and who their friends and enemies were, and what their mood might have been at the time of the shooting. That’s no easy feat, and though Joyce insists the department receives good intelligence, only 44 percent of homicides were solved last year, according to the FBI. This doesn’t bode well for Commissioner Ed Davis, who two years ago strengthened the homicide unit in response to similarly low clearance rates.


If anything, the Boston Foundation’s street workers will look to reclaim the glory of the 1990s. It’s not as if the street-worker program dropped off entirely, either: Both the city and the Boston Ten Point Coalition employ their own street workers, who work the day shift and go where the trouble is. The Boston Foundation takes the night shift—from 4 to midnight—and assigns its workers to patrol only five mini neighborhoods in the South End, Dorchester, Roxbury, and Mattapan. This specialization will build trust between workers and young thugs. Information will flow. The irony is what the street workers will do with that.

Nothing, really. Cops like Joyce signed off on the street-worker program not least because Commissioner Davis is a big proponent of community policing. But the street workers won’t be sharing any information with the cops; Lewis and Byner and the street workers themselves are firm on this point. To do otherwise would break the trust they have with the kids.

So the cops will instead regularly stop by the street workers’ meetings, and debrief them on all criminal activity in their neighborhoods. The street workers, in turn, according to one who didn’t want to be named lest he jeopardize his standing in the neighborhood, will offer the cops vague information when they hear something, and ask that a patrol car be on a certain block at a certain hour. The workers can then go back to the kids and tell them that the cops have heard about their plans, and advise them to call it off for the night.
With the street workers serving as the leaders the gangs once had, “everybody wins,” this street worker says.

This program is structured on competing groups’ trusting each other. Trust is all anyone has here. The kids must trust the street workers will keep their secrets; the street workers must trust themselves—especially the ex-cons among them—that they can walk their old turf without enjoying its trappings; the cops must trust the street workers for the same reason, as must Robert Lewis Jr., that the street workers he’s vouching for don’t betray him; the Boston Foundation must trust Lewis, as he leads it into uncharted territory; the city of Boston, especially the mayor’s office, must trust the foundation when it says it’s out to better Boston, and not score political points, a long-held suspicion among Menino’s ranks.

It could go on, too. Lewis says there’s talk of presenting President Obama with a plan to launch similar programs in 12 cities if ours works well first.

And to think that the whole thing rests on the shoulders of men like Vito Gray.


It’s a clear Friday evening in June, about the only rainless night the month will offer. But it is not a quiet one, at least not in Kevin Ryner’s Ford Explorer, heading to the night’s first patrol stop for the Morton Street street workers, the Perkins Community Center in Dorchester. “Swag Up,” a song featuring Jamie Foxx and Rick Ross, blares from the CD player: Ain’t no way, no how, you got more swagger than me. Ryner is sitting way back in his seat, shades on, windows down, head bopping with the beat, all of Blue Hill Avenue taking notice. He’s downright scary-looking. Broad frame. Big, bushy beard. Red Sox cap pulled low, the bill as straight as the day he bought it. If he were to take his aviator glasses off, you would see that his eyes are crossed.

And yet he emerged from Dorchester clean, received a degree in sociology, and for the past 10 years has done youth work in the Grove Hall area of the neighborhood, teaching the kids he works with how to play chess, plant a garden, drop a beat in the studio he owns with his brother. He’s been married for 16 years and counts his son staying out of the penal system and getting into college as his greatest achievement.

Riding shotgun is Greg Simpson, another street worker, also with aviator shades on, also shaking his head to the beat. Simpson played pro basketball in Italy, moved back to Boston in the 1980s and started doing crack. He lost his money in a year and a half. He took to robbing Christy’s convenience stores to support his habit. The press called him the Christy’s Bandit. He guesses he probably robbed 40 or 50 of them. It was easy. Just show the gun in the belt when the cashier was cashing out. The gun, though, was never loaded. Simpson couldn’t stand the thought of actually killing someone. Probably put him in more danger than the stupid cashier. Yet he persisted: He once robbed the same Christy’s four times in one day. By the last time, the cashier started handing over the money when Simpson walked in the door. Crack will make you do the craziest things. He did 10 years for his habit. Today he’s an assistant basketball coach at Madison Park High, where he once starred.

Vito Gray sits in the back seat, his flat-billed Red Sox cap worn slightly askew, no shades on, looking straight ahead. After he got out of prison in 1997 he was angry—angry that the courts had deprived him of his earning potential. He went right back to dealing, right back to running Mission Hill. Three years later he got a four-year bid for dealing crack. This stint changed him. He came out in 2004, at age 34; he’d been dealing for 20 years and had nothing to show for it, few worldly possessions but remembered plenty of the aging corpses he’d known as users all those years. He sought out Pastor William Dickerson II of Greater Love Tabernacle in Dorchester. Dickerson’s church was once in Roxbury, back when Vito was the Vito of old. Dickerson would bump into him, tell him he’d like to talk to him. Vito said little beyond hi and bye. Now Vito came to him and said he didn’t know if Dickerson would accept him for all that he’d done. Victor Woods had been a member of Dickerson’s church.
But Dickerson welcomed Vito. “A dirtbag like me,” Vito says. Never had he known such forgiveness, such love.

He has not forgotten it. Before they departed this afternoon, Vito led his fellow street workers in prayer. That sullen look of his, here in the car, is actually exhaustion: Vito goes every day to Dickerson’s 6 a.m. service after leaving his street-worker shift at midnight. Tonight, during his dinner break, he’ll go to Bible study at the church.

But first Ryner stops in front of the Perkins Community Center on Talbot Avenue. Vito gets out and heads inside. In the hallway is a long plastic table and three chairs. In a few minutes, a 25-year-old named Jarvaiid Jackson walks over. He’s biked here and his hands and chest are damp with sweat. “Are you Vito?” he says.

Jackson is wiry, wide-eyed, dark-skinned, dreadlocked. He’s meeting Vito because he has a drug case and possible jail time waiting for him unless he can show his parole officer gainful employment. Vito heard about Jackson from an employee at the Mildred Avenue Community Center in Mattapan earlier this week. He agreed to meet Jackson here.

This is Vito’s first breakthrough with a possible one-percenter, and his excitement is palpable. “I’m just like you; the only thing is that I’m older,” Vito says, elbows on the table, leaning forward. “I was once 25, too. Heavy industry selling drugs, you know?” He’s talking fast, far faster than he ever does. “Right now my main objective is just trying to, you know, stop young men like yourself from going down that road.” He asks Jackson questions but doesn’t give him a chance to respond. He’s already on to his next point. “I’ve got to make sure that, you know, you fit the criteria, meaning that you have job-training skills. You know what I’m saying? Because that’s important. Don’t just say you want a job when you don’t have no job-training skills. What can you do? Because when you go on an interview, that’s what they going to ask you. Like what was your past job? What can you do? What can you offer us? So, you know, you need to answer these questions in a proper way….”

Jackson is ultimately able to squeeze in that he’s worked in the health field helping kids with multiple sclerosis but was laid off after his arrest. He’s done hustling, he says. He wants real work again. Now Vito switches roles on him. Goes hard. Tells Jackson that, according to his record, he dealt when he had legitimate work. “You had a job and you still hustled,” Vito says. “So what make me think that you get a job now you not going to still hustle?

“Game recognizes game,” Vito says. “So let’s just be mindful of that. Because once I get you a job I expect you to keep it…fast money comes, man, but look. I’m telling you that I did almost 12 years in prison—selling drugs and almost killing someone—and I’m telling you that hustling and working…it don’t mix.”

Jackson seems in awe of this kind of honesty. He slowly offers his own. “I’m still mad at myself,” he says. About his case. His missed opportunities. Everything.
Vito knows he has him now. He is a born leader, after all, and Jarvaiid Jackson is just the latest young man that he might mentor. The only thing that’s changed is Vito’s curriculum.

Jackson has a court hearing Monday for his drug case. Vito says he’ll accompany him, argue on Jackson’s behalf.

“Just give me a call Sunday night,” Vito says, “and we’ll meet up Monday morning.”

Jackson says he’d like that.

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