Q: What’s the Best Way to Turn Around a Young Street Thug? A: Maybe with a Former Street Thug.

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.

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.


  • Alice H.

    At 93, I don’t feel equipped to do something more specific than applaud the street workers and Boston Foundation. And I applaud every young person who responds to an opportunity to hold down a job, which won’t pay what dealing in drugs does.
    Now to make a contribution to Boston Foundation.

  • Alice H

    see above