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A second act for a boy named Trinidad

Two paths diverged in his Cambridge neighborhood —the gang and the stage—and he chose both. But now he is following the footlights toward safety

CAMBRIDGE - On a Saturday night in March, in a tiny, paint-splattered storage room in Central Square, Trinidad Ramkissoon pirouettes between 12-foot-high lavender curtains and, waving a wand, pronounces himself the tooth fairy. He speaks in exaggerated tones and waves his arms with dramatic flair and not a hint of embarrassment at the decidedly nonmacho move.

The 17-year-old with the baby face and flowing, shoulder length hair, is rehearsing his role in “Money Matters,’’ a play staged at the Central Square Theater by Youth Underground, a teen theater troupe.

This is one side of Trinidad Ramkissoon.

This is the other: One hour after rehearsal concludes, after the last of the other teens has left, Ramkissoon, who has stayed behind for extra coaching, shakes off his perpetual smile, pulls the folded red handkerchief out of his right rear pocket so that it dangles like a flat, pointed tail, and walks into the night. Several blocks from the theater, three young men emerge from the shadows and greet him with complicated handshakes. They are members of the Bloods street gang - fellow members.

Trinidad Ramkissoon (with umbrella) stopped to talk with friends in his Cambridge neighborhood.JONATHAN WIGGS/GLOBE STAFF/Boston Globe

Ramkissoon, who was born and raised in Cambridge, has been a Blood for nine years. For as many as seven years he was “active,’’ engaging in activity that, he says, was criminal or toed the line. But a little more than four years ago, the gang’s grip on Ramkissoon’s life began to loosen; he had been introduced to theater and found that he loved it.


As a result, though Ramkissoon still considers himself to be a member of his “second family,’’ he has spent the past couple of years distancing himself from the world gangs represent.

“I’m doing good things now, because I want to,’’ he said. “But I also have connections to my old life, because I have to. But in the end, this theater thing? This is my life. I love this like my mother. And this is where I’m taking my life. I’m good at this. I can be great.’’


On his own

Ramkissoon, the youngest of seven siblings, grew up in a crowded household, and from an early age often felt he had to fend for himself. When he was 8, his family’s house burned and they found themselves temporarily homeless. At about that time, too, his brother was imprisoned for stabbing a man. Meanwhile, the youngest of his five sisters stopped spending time with him because she was busy preparing for college.

His father, a hotel worker, had a grueling schedule that often kept him away for 16-hour days, six days a week. It was all his mother could do to manage a household that large.

“Trin was a lone wolf,’’ Henrietta Ramkissoon said of her youngest. “Even at that age no one could tell him what to do.’’

Left to his own devices, Ramkissoon began tagging along with a cousin visiting from New York City, where he was a Blood. The boy decided in second grade to be like his cousin.

“He filled a role that my brother and my youngest sister had not filled,’’ Ramkissoon says. “He didn’t want me to be in, but you see how I am now, stubborn? I was worse then. And I was like, ‘I’m doin’ it, and that’s that.’’’

In the summer of 2002, Ramkissoon was sworn into his Bloods chapter, comprisingdozens of young men and boys, mostly African- and Caribbean-American, preteens to mid-20s.


“I started to do work, to get in the streets right away, because I wanted to prove myself,’’ Ramkissoon says.

While he acknowledges “doing things some people might consider crime’’ he is willing to talk only about two incidents for which he was arrested. Ironically, neither had anything to do with his gang relationships.

Ramkissoon’s juvenile criminal record is sealed, so there is no way to verify the trouble he’s seen or done. But he says that when he was 12 he was arrested and escorted by police from Fletcher-Maynard Academy in Cambridge for possession of drug paraphernalia and a knife. A plea agreement in that case landed Ramkissoon on probation, and he was suspended from school for 60 days, he says.

While on suspension, Ramkissoon reconnected with Terry Walker, a Roxbury activist, mentor, and talent agent who had introduced Ramkissoon to modeling and musical talent shows when the boy was in third grade. Aside from Ramkissoon’s confidence, Walker says he has a uniquely exotic look that is perfect for modeling.

Indeed, some of Ramkissoon’s “civilian’’ buddies jokingly call him “pretty,’’ a reference to that hair.

Ramkissoon takes the ribbing in stride, “blaming’’ his looks on his family’s Caribbean roots - his parents are natives of Trinidad.

Trinidad’s mother, Henrietta Ramkissoon, says her son was always a ‘‘lone wolf.’’JONATHAN WIGGS/GLOBE STAFF

“We did catalog stuff, local modeling shows,’’ Ramkissoon says of his work with Walker. “I would [also] rap wherever I could get a crowd - on the street corner, wherever. So Terry started getting me shows. But I had to be kind of closed about it at first.’’


Closed, because he feared how other Bloods would react. Ramkissoon says he had many a bruise and black eye to show for defending his modeling, which some of his gang peers saw as an unmanly distraction.

In spite of the internal conflicts, the only other serious trouble Ramkissoon says he has been in occurred last year, when he claims he inadvertently struck a police officer who had responded to a call to his parents’ home to break up a heated argument between one of his sisters and the boyfriend of another.

Ramkissoon again entered into a plea agreement, this time on one count of battery on a police officer, he says. In exchange for the plea, his felony charge was reduced to a misdemeanor and he was given probation, which is set to end in July.

As for his other activities, “it’s probably not smart for me to go into detail on things I never got in trouble for,’’ Ramkissoon says, reiterating his earlier disclaimer that “some people I’m associated with might have done stuff considered criminal. Drug dealing? It happens, but no loyalty could force me to do that. Fights, beat downs? They happen.’’

Ramkissoon insists he’s not being vague to be cute. Getting too specific about Bloods activities, he says, could put his life in jeopardy.

A new direction

In the summer of 2008, just months before Ramkissoon started his freshman year at Cambridge Rindge & Latin School, he found himself dissatisfied with his modeling and musical performances and began nursing another dream.


A teacher of his, and friends, had told him about Youth Underground, which was launched in 2006 under the auspices of the Underground Railway Theater company. And a chance meeting with Dr. Elaine Koury, a veteran actor and director of visual and performing arts at Rindge & Latin, had deepened his interest in theater.

“I remember the first time I saw Trinidad,’’ said Koury, a popular educator with a reputation for not taking guff from kids. “He and some other young men were standing in the hallway outside my office talking, and they were loud. And they should have been somewhere, not loitering. So I confronted them.’’

Ramkissoon is bashful when asked to recount this moment. He made the mistake, he says, of mouthing off to Koury and refusing to give her his name.

“I found out who he was, and our assistant principal brought Trinidad to my classroom,’’ she says. “And he was quite contrite and apologetic. I let him know that I would not accept disrespect, because I had not disrespected him. And that’s where our relationship started. He wasn’t used to being put in check.’’

After getting to know Ramkissoon, Koury says she observed that “he commanded a following; he was like the pied piper. He had a flair for the dramatic. And he wasn’t shy or self-conscious.’’

Eventually Koury cast Ramkissoon as a lead in “Hi Gear,’’ a play she had written; the plot coincidentally involved a young gang leader trying to find his way out of that life.

“He was a natural, brilliant,’’ she says of his performance.

Before “Hi Gear,’’ though, Ramkissoon applied to Youth Underground, where he met Vincent Ernest Siders, the other adult he says has changed his life for the better. Siders, also big on Boston’s theater scene, is Youth Underground’s lead teaching artist.

In his first audition for the group, Ramkissoon recalls Siders getting in his face and telling him he would never be a good actor if he couldn’t let down his guard and loosen his emotions. To do that, Siders said, he would need to let down his guard, to let his secretive self “die.’’

Iris Smith-d’Agincourt and Trinidad Ramkissoon in rehearsal for the Youth Underground production of ‘‘Money Matters.’’KAYANA SZYMCZAK FOR THE BOSTON GLOBE

“It sort of freaked me out at first, ’cause the life I was living? I didn’t even want to think about dying, not even on stage,’’ Ramkissoon said. “But it opened something up in me. And even more it connected me with Vincent, who took on a father role with me and started saying what I needed to hear - even when the words have been tough and I haven’t liked what he was saying.’’

Siders agrees that Ramkissoon’s first audition was necessarily intense.

“Trinidad is a complicated kid,’’ Siders said. “He has been in the streets for years. And even back then he was craving a creative outlet.’’

The pair’s relationship grew, with Siders serving the role of strict mentor and Ramkissoon increasingly staying late after Youth Underground rehearsals, begging Siders for more instruction.

Siders, who introduced Ramkissoon to some of his own mentors and peers in Boston’s theater community, says he quickly figured out that Ramkissoon was staying late for that extra coaching and working part-time jobs, in part to avoid being tempted or required to “ride’’ with his gang.

He has helped Ramkissoon land other auditions, including for the play “Into the Woods,’’ which kicked off a short run April 27 at Hibernian Hall in Roxbury, and “The Last Shot,’’ a feature film shot in Boston last year, in which Ramkissoon has a brief role as - what else? - a teenager.

“He has grown so much as a performer from when he started,’’ Siders says. “He’s a real talent and in theater, a success story. Now it’s important that all of his life match that success.’’

Maintaining ‘family’ ties

Ramkissoon insists that his acting career will continue to grow. And the likes of Koury and Siders say he should have no problem.

“You can’t over-emphasize what his intensity means,’’ Koury says. “The most successful directors and actors will tell you that the best are those who are so intense that they live their roles. They believe in their roles almost religiously. That’s what Trinidad has that can’t be taught.’’

If there’s an area Ramkissoon could use improvement, his mentors say, it is taming his stubbornness.

Ramkissoon dropped out of Rindge, following his junior year, rather than accept being held back a grade.

“I admit now, I wasn’t reading well and wasn’t taking my lessons as seriously as I should have,’’ he says. “But I’m fixing it now.’’

Indeed, Koury, who says Ramkissoon is the most resilient student she’s known, has been tutoring him for months, to prepare him for his GED exam. Ramkissoon also says he’s watching his behavior and is attending probation meetings faithfully.

Asked why he still wears the gang flag, the red bandana, on occasion, Ramkissoon offers this explanation: “This was a family connection for me for a long time, and sometimes I wear it just to own that, to, like, acknowledge it.’’

So can he really ditch the Bloods, or does he even want to?

Ramkissoon says there is no yes or no answer, because his chapter isn’t likely to let him “officially’’ walk away. He says that till now he has been content with the fact that an increasing number of his gang peers have accepted his burgeoning entertainment career and no longer ask him to participate in their activities.

Chris Byner, director of external affairs for the Boston Centers for Youth and Families and former director of Boston’s Streetworker program, which helps gang members transition to real jobs, says Ramkissoon’s explanation makes sense.

“It is common for young people who choose to change their lives maintain that formal connection, even while no longer living that life. Others are more fortunate, and their sets do let them leave,’’ Byner said. “It’s a sign of the times that a young person who tells his gang peers, ‘I have a new life, a new focus, a plan to go straight and stay straight,’ is likely to garner respect from them for having a plan.’’

Struggle of good and evil

On a recent rainy Friday afternoon, Ramkissoon paces The Port, his Cambridge neighborhood, reciting lines from “Into the Woods.’’ He calls out to teens to “zip up that jacket’’ and “pull that hood up,’’ scolding them that they could catch colds. They sheepishly comply and respond as they would to a parent: “I know!’’ and “Sorry ‘bout that!’’

He treats peers like his children and elders like peers.

Vincent Ernest Siders instructed youths during a rehearsal of ‘‘Money Matters.’’ From left, Melissa Belance, 17; Juan Arevalo, 14; and Trinidad Ramkissoon.KAYANA SZYMCZAK THE BOSTON GLOBE

Jeffrey Sanders, 50, a building contractor and neighbor, says he admires Ramkissoon.

“Unlike a lot of his peers who say once in trouble always in trouble, this boy has embraced the acting thing,’’ said Sanders, who was involved in gangs as a teen. “And in the world he comes from, that’s brave. I know his good vs. evil struggle. And I think he’s handling it pretty well.’’

Danny Vazzquez, 19, recalled Ramkissoon as “a little gangster back in the day.’’

With a nervous laugh he quickly added, “The craziest thing though, is seeing how committed he is to this stuff. You can see him walking around the ’hood now reciting lines and stuff, looking at scripts. He’s serious!’’

“Sage’’ is how 21-year-old Vladimir Flores, a photographer, describes Ramkissoon.

“I still remember the first time I met him, before he moved on to his theater life,’’ Flores says. “This little dude with this long flowing hair stepped up to me on the sidewalk and looked me hard in the eye and asked, ‘You know what the number one thing is that holds people back and prevents them from succeeding?’ I shook my head, wondering who this kid was. He never blinked, then answered one word, ‘fear.’ Then he walked away.’’

Ramkissoon says now that he got that question from a poem a former teacher had taught him.

“I don’t remember which one that was,’’ says Carolann Nolan, that fourth-grade teacher. “But I do remember telling him as young as 9 years old that he would end up dead or in the streets if he didn’t change. And that’s a speech that you normally save for much older kids. He needed it then. And I’ve kept up with his developing theater career. He’s had some bumps. But it seems like he took it seriously.’’

James H. Burnett III can be reached at james.burnett@globe .com. Follow him at www.twitter .com/jamesburnett.