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

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.


  • 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