E-Mail This Article to a Friend Coming home Accused murderer Shawn Drumgold was sentenced to life without parole in 1989. Last month, his conviction vacated, he walked free. The story of this former drug dealer offers a glimpse into the gray area between guilt and innocence. For Drumgold, it raises a single overwhelming question: What now? BY CHRIS WRIGHT

There’s an almost mythical quality to the name Humboldt Avenue.

The street itself is nothing remarkable: a stretch of residential buildings, some dilapidated, some not; a convenience store; an Edison plant and, beside that, a Jehovah’s Witness center. Just your average city street. Except it isn’t. Humboldt has a reputation. You hear the name and you think gangs. Kids in hooded sweatshirts, their pockets stuffed with bags of heroin and crack cocaine. Creeping SUVs, their tinted windows hinting at the menace within. The boom of hardcore rap. The rapid beat of gunfire followed by screams, screeching tires, sirens, sobs. And somewhere, maybe, nihilistic laughter.

Of course, there are plenty of ordinary, decent people living on Humboldt Avenue. Kids here go to school. Parents go to work. But Humboldt’s reputation is not merely the result of white suburban angst. This Roxbury street and its surrounding neighborhood was the epicenter of the drug violence that raged in Boston through the 1980s and early ’90s, and which, to a lesser extent, continues today. Two of the city’s most brutal gangs — the Humboldt Boys and the Castlegate Raiders — have long been engaged in a bloody turf battle here. And it was on Humboldt, on a balmy evening in August 1988, that one of the most notorious murders in this city’s history took place.

The victim was a 12-year-old local girl named Darlene Tiffany Moore. Moore had been perched on a mailbox, chatting with friends, when gunfire rang out. Though the shots were reportedly directed at a gang member sitting nearby, three bullets tore into the little girl — two into her back and one into her head. She died shortly afterward. Across the country, Tiffany Moore’s murder elicited outrage, fear, and a lust for revenge. Here in Boston, there was a sense of something approaching mob fury in the hunt for her killer. People wanted the perpetrator punished, and they wanted it done quickly. Ten days later, the police charged Shawn Drumgold, a 23-year-old local drug dealer, with the crime.

There was no physical evidence linking Drumgold to Tiffany’s murder, but as his trial wore on, circumstantial evidence began to build against him. Although the shooters (there were three of them) had worn masks, one witness testified that she had seen Drumgold leaving the scene of the crime shortly afterward, tucking a gun into his belt. "I seen his eyes," the woman said. "They were, like, staring." Other witnesses said they had heard Drumgold talking in advance about shooting someone. Though his alleged accomplice, Terrance Taylor, was eventually acquitted, things did not go as well for Drumgold.

On Friday the 13th of October 1989, he was convicted and sentenced to life in prison without the possibility of parole.

‘Man, he ain’t never getting out of jail’

"This is where it happened," says Drumgold, gesturing at a mailbox. "I lived over there." The house where Drumgold was staying at the time of Tiffany’s murder, directly across the street from where she was shot, is no longer there. But then, a lot has changed since he went away. At the time of Drumgold’s conviction, Ray Flynn was the mayor of Boston. The elder George Bush was about to prosecute a mini war in Panama. You could buy an LP record for $6.99 and a state-of-the-art Smith Corona typewriter for $159.99. The night Drumgold took up residence in his cell at Walpole, Meat Loaf played to a packed house at the Channel.

Things have changed for Drumgold, too. He earned a GED while in prison, took a few college courses, found Allah, and developed a taste for Hershey bars. "My mother said to me, ‘If you’re feeling down, eat chocolate,’ " he says. "So I ate chocolate, and for some reason it boosted my spirits. Three or four bars, I had a good week. I don’t know why. If my mother is telling me to do something, there must be a reason." While Drumgold was eating chocolate, however, the rest of the world moved on. His children grew up. His marriage broke down. People close to him died or just drifted away. "Separation and loss": Drumgold uses phrases like this often. "Everyone disappears." It’s a theme with him.

There is good reason for this. Over the course of 15 years, prison visiting hours can start looking pretty thin — particularly for the lifer. "I didn’t want to let no one go," Drumgold says of the family and friends who came to see him. "I was looking for commitment from people who couldn’t commit, because of their sadness. They stopped coming because they didn’t want to see me that way." He recalls a long-ago visit from his wife, Rachelle, when another inmate called out, "Why you coming to visit him? Man, he ain’t never getting out of jail."

The inmate was wrong.

Recently, in the wake of an extensive article by former Boston Globe investigative reporter Dick Lehr, Drumgold was granted an evidentiary hearing, during which a number of prosecution witnesses recanted their original testimony. Others came forward to confirm Drumgold’s alibi for the day of the murder. It emerged, for the first time, that one of the prosecution’s most damaging witnesses — "I seen his eyes" — had been suffering from brain cancer at the time of the trial, which likely impeded her ability to give reliable testimony.

And it got worse. During the hearing, Superior Court judge Barbara J. Rouse heard evidence pointing to what Lehr describes as "strong indications of police and prosecutorial wrongdoing": a police report regarding a viable suspect filed 13 months after the fact; spurious characterizations of Drumgold as a gang member; interviews conducted under dubious circumstances; perks given to key witnesses; threats leveled against others. Finally, Suffolk County prosecutor David Meier filed papers stating that Drumgold’s conviction was open to question. For its part, the office of Suffolk County district attorney Daniel Conley issued a 30-page report that concluded with the line: "[T]he testimony and exhibits introduced at the motion hearing in 2003 lead to one inescapable conclusion: that justice may not have been done."

To some extent, the key word in Conley’s report was "may." While Judge Rouse did vacate Drumgold’s conviction, the DA’s office refused to exonerate him. So Drumgold, who would like to work as a counselor for high-school kids, is now subject to the CORI (Criminal Offender Record Information) law, which means he’ll have difficulty securing any position working with children. Conley, while announcing that he would not retry Drumgold for Tiffany Moore’s murder, also flatly refused to issue an apology for the 15 years Drumgold spent behind bars. "What I owed Shawn Drumgold," Conley said in a press conference, "he got." In any event, on November 6, Drumgold walked out of prison a free man. "It’s wonderful," he says of his newfound liberty. "I can smile now."

But Drumgold knows, too, that things aren’t necessarily going to be easy. "I’ve had to ask myself," he says, "what am I going to do now? What kind of job am I going to get? Where do I want to live, and do I have the means to live there? What about a driver’s license? Health care? Dental care? I have to run around looking for a job, and this is a time when jobs are scarce. I don’t want to be a burden to my family." As Drumgold says this, he picks through a piece of chicken he’s ordered at a fast-food restaurant. He hasn’t had much of an appetite lately. "I’m looking at a lot of new stuff," he says, pushing the chicken aside. "I don’t even know how to travel from one place to another."

The sandwich incident

The first time I meet Shawn Drumgold, to have lunch with him and his mother, Juanda, he is 45 minutes late. He arrives at the Harriet Tubman Center — the South End social-services center where Juanda volunteers — looking a little flustered. He’s traveled here from Porter Square, he explains, and got lost riding the T. A few minutes later, as we discuss where to eat lunch, Drumgold pulls his mother aside. "I’m broke," he tells her. "I’ve got 13 bucks in my pocket." He is also unable to find his wallet. We decide on a sandwich shop on Mass Ave. As we stand in line, I ask Drumgold how old he is. Without missing a beat, his mother turns around and answers the question for him: "He’s 23" — the age her son was when he went to prison, 15 years ago.

Upon his arrest in 1988, Drumgold’s picture was printed in newspapers across the country. Back then, gang members were the nation’s terrorists, a looming menace that threatened our way of life, and — in Boston, anyway — Drumgold’s face became as familiar as Mohamed Atta’s is now. The figure we saw in the papers said violence. It said social dissolution. It said you are not safe. Drumgold’s was a face to be reviled and dreaded: the face of evil. At least, this was the tone of the media at the time. The day after his arrest, the Boston Herald ran a grainy mug shot of Drumgold under the banner headline: ‘TIFFANY KILLER’ JAILED. Even today, you look at that picture and think, Ugh.

In person, Drumgold cuts a remarkably different figure. He’s not what you’d call a towering man — five-foot-six — and, at about 180 pounds, he’s not what you’d call skinny, either. But he has a friendly, handsome face that seems caught between amusement and melancholy. His narrow, tilted eyes are thick-lashed, his nose and cheeks a little fleshy. His clothes — plaid shirt, padded jacket, blue jeans, black sneakers — are all brand-new, like a baby’s. Even his freshly shaven head and little mustache cannot detract from the overall impression that Shawn Drumgold is, well, almost cuddly.

Drumgold’s manner is equally at odds with the gang-banging, Tiffany-murdering persona laid on him all these years. Though his voice bears the languorous lilt of the street or the prison yard, he is soft-spoken, thoughtful, unflaggingly polite, and emotionally astute. At one point he gives me a half smile and says, "I’m wondering what’s going through your mind." I tell him I have a date that night, I’m thinking of that. "Listen to her," he advises. "Don’t ask too many questions, but listen." Over the course of three days, not once do I hear Drumgold use profanity. At times, this onetime drug dealer seems almost timid.

As we order our sandwiches, Drumgold has a misunderstanding with the woman behind the counter. "What do you want on it?" she asks. "Coffee," he replies. The woman, who clearly is not having a good day, rolls her eyes. "What. Do. You. Want. On. Your. Sandwich?" Shawn winces a little and says, "Mayonnaise?" To some extent, this passive response can be chalked up to the 15 years Drumgold spent in prison. There, you get used to people making decisions for you — you’re like a child in a way. The grumpy sandwich woman is, in this situation, in a position of authority, and when you’re behind bars you soon learn that it doesn’t pay to quibble with authority figures. And yet there seems to be something more fundamental going on here.

The fact is, Drumgold is either a very good actor, or he is a very nice guy. Over the course of three days, I see dozens of instances that suggest the latter. At one point, he dashes out of a KFC to give a woman a dry-cleaning slip he thinks she left behind. When informed by a potential employer that he’s being turned down for a job he’d previously been offered, one he’d had great hopes for, he thanks the woman profusely for her time. Walking past a photo lab near his home, he exchanges a wave with the proprietor, with whom he has recently grown friendly. Standing in a lecture hall at Boston University — Dick Lehr has asked Drumgold to come in and talk to his journalism class — he shuffles his feet bashfully and seems less interested in talking about his own hardships than those of others, people who have been "forgotten, left behind."

Even before he went to prison, while he was still "running the block" on Humboldt — selling drugs — Drumgold had a reputation as an easygoing guy. During his trial, one of the prosecution witnesses described him as "friendly." "He got in with the wrong people," his mother says, "but even then he was still helpful, still polite. That’s the kid he was." Of course, this is a mother talking, an unreliable witness. Drumgold himself has three kids — an 18-year-old son, Shawn, and a 20-year-old daughter, Rashanna, in New York, and here in Boston, from his marriage with Rachelle, a sweet, bright 15-year-old daughter named Kiara. When you see how loving Drumgold is with Kiara, his mother’s claim that he is a "sweet" person seems more believable.

‘I was a well-respected man in the neighborhood, although I was a drug dealer’

Recently, as I was telling a friend of mine about Shawn Drumgold’s nicer points, she interrupted me mid sentence: "Oh, give me a break!" This is an understandable reaction. There is a temptation to harbor bitterness toward Drumgold, or at least suspicion, to say, "Even if he’s not guilty of this crime, and maybe he is, he’s guilty of something." It’s true. Drumgold didn’t get a fair trial back in 1989, but there are only a handful of people who can say with absolute certainty who shot Tiffany Moore. And Drumgold was guilty of something. He was an admitted heroin dealer who, in the three years prior to being picked up for the Moore murder, had served two separate 10-month sentences for possession with intent to distribute. In fact, at the time of his arrest for Tiffany Moore’s murder, he had just been caught in possession of 26 bags of heroin.

"Shawn was no angel," says his mother. "He was known on the street."

As Drumgold tells it, even his fabled affability is open to question. "Selling drugs is a business," he says. "And any business, you have to protect your best interests. So my best interest was making people comfortable, because coming into a drug-infested area is scary to some people. So the more comfortable you make people feel, the more protection you give them where they can come buy something and leave without being robbed or getting harassed, the more money you will make. So that’s what I used to do, give people more access so they could get what they want and get out of there. People didn’t have to feel intimidated by me."

Friendly or not, Shawn had violence in his life back then. One recent chilly morning, I accompany to him a health clinic to fill out insurance forms. He needs treatment, he says, for chronic pain caused by a bullet lodged inches from his spine. The bullet has been there since 1984, when he was shot as he approached someone who owed him money. "He thought I was going to hurt him," Drumgold says. "I ran up and he had a gun. He was going to shoot me. So we started fighting over the gun and fell down some stairs." There are days when Drumgold can barely move because of the pain his old injury causes him. Nonetheless, he counts himself lucky. "There’s a lot of ramps in my neighborhood," he says. "I could’ve been in a wheelchair."

Then there’s Drumgold’s account of his whereabouts on the day that Tiffany Moore was killed, an account which reveals that he had a violent streak of his own. "That whole day, I stayed in the house," he says. "I had a little daughter who was a few months old. So I spent the day with her, changing diapers, feeding her, spending time with my daughter, just a normal day. That night, I met some friends, and we was riding around for a little while. At the time Tiffany was murdered, we was up on Sonoma Street. I had no knowledge of the shooting until we left Sonoma Street and went to Humboldt. When we got to Humboldt, there was a little girl laying on the ground. So I asked this guy Charlie, ‘Is that my sister?’ Because prior to that shooting, a week earlier, I had shot this Jamaican dude named Eric. There were rumors running around that we was feuding. So I thought that he had shot my sister because he couldn’t get to me."

A week or so later, as Drumgold was being arraigned for the drug-possession charge, he heard someone use the word "murder" and was gripped with a creeping sense of panic. "The strangest thing," he says, "they was talking about the [Moore] murder, and I thought the kid Eric had died. That’s where my mindset was. I was like, Whoa! I didn’t actually know it was Tiffany they was charging me with until the judge allowed them to take me out for fingerprinting and photographing. That was when I found out they wanted to ask me questions about the Tiffany Moore murder. Once I realized it wasn’t Eric, I was relieved. That took pressure off me, you know, facing a murder charge. Little did I know."

Eric, he adds, "turned out to be okay."

"I’m the same character at a different time," he says. "I know right from wrong more now, my interest in hustling and stuff like that, being on the street, I know that’s counterproductive to me today, but I never changed. If you’d have known me 15 years ago and knew me now, I’m the same person." He adds that, shortly after his release from prison, a member of the Humboldt gang warned him off trying to take over his old block. The gang member did add, however, that Drumgold was welcome to come work for them if he liked. He declined the offer. "I’m strong enough not to resort back to my wicked ways," he says. "I’ve just got to be patient."