Flying lessons: Debbie Jacob’s Wishing for Wings

When writer and teacher Debbie Jacob volunteered to teach English classes at Trinidad and Tobago’s juvenile detention facility, she had no idea how hard the challenge would turn out to be — or how rewarding. Now she hopes her book about the experience will inspire others to reconsider the fate of young offenders. Erline Andrews finds out more

Debbie Jacob. Photograph by Kim Johnson

Jahmai Donaldson was a troubled teenager so enamoured of rap stars that he had his teeth replaced with false ones made of gold and diamonds, similar to the popular American hip-hop artist Lil Wayne.

“Following the wrong crowd” eventually landed Donaldson in Trinidad and Tobago’s Youth Training Centre — juvenile prison — where he continued his trouble-making ways, getting into fights and regularly being put into “lockdown” or solitary confinement. He recalls being taunted by guards who told him that when he left prison he “would amount to nothing.” For a time, he believed them.

Today, Donaldson, now twenty-two, is a very different young man. He may have the gold teeth for the rest of his life, but his attitude and goals have changed entirely. I couldn’t pin him down one recent Saturday morning, because he was on his way to a class at the University of the West Indies — one of five courses he’s taking to earn a certificate that is his first step towards a degree in either psychology or social work.

“I want to help people,” he says of his degree choice. “Plus, the human mind is very interesting.” Donaldson credits the change in his life to someone whose background is very different from his own.

Debbie Jacob grew up on a remote farm in rural Ohio. She moved to Trinidad three decades ago, after falling in love with the country and the Trinidadian who would become her husband. She’s the head librarian at a private school for expats and well-off locals; for a time she taught English there as well. She’s also a columnist for the Trinidad and Tobago Guardian, known mainly for her thoughts on local culture and education. She’s written a children’s book, a collection of short stories, and a handful of study guides for Caribbean literature.

When she volunteered in 2010 to teach O-level English language to a small group of young inmates at YTC, Jacob wasn’t sure what she was getting into. At first, it seemed her worst expectations would be realised. Her students were moody, prone to anger and fighting. Some dropped out of the class. Some — like Jahmai Donaldson — missed many classes from being in lockdown.

Jacob had to bridge distrust, insecurity, and other emotional barriers before she could even begin to prepare them for the exam. And she had only eight months to cover a syllabus that normally required two years.

Today, Jacob is more confident about her ability to reach challenging students, and more committed than ever to teaching young men like Donaldson. She’s also speaking out on an issue she hadn’t thought about prior to teaching at YTC: the plight of young men — some of them innocent — seeing their youth drain away as their cases drag on in an inefficient court system.

She credits the change to her first students at YTC, with whom she formed a bond that continues. “I learned so much more from them than they ever learned from me,” she says. “I taught them some academic things, and they forced me to face a lot of issues in my life that I had never faced, like how not to just become depressed or give up when things get hard.”

Jacob chonicled the extraordinary story of her relationship with her students in a series of newspaper columns, starting in 2011. She subsequently adapted the articles into a book, Wishing for Wings, which has received praise from readers and reviewers since it was published in October 2013. And the story is now in the early stages of being made into a documentary. Trinidadian writer and filmmaker Kim Johnson is producing it, and has brought on board award-winning Spanish director Miquel Galofré, whose 2013 film Songs of Redemption, set in Jamaica, also dealt with life behind bars. “Instantly upon reading it,” says Johnson of Wishing for Wings, “I saw its potential. I thought, ‘This will make a good film.’”

One of the remarkable things about Jacob’s story — and the reason she overcame obstacles and got good final results — was her willingness to do whatever it took to get her students to succeed. She wrote them letters of encouragement, and got teachers from her school and her daughter Ijanaya to do the same. She requested and collected book donations for them. She even essentially ignored the recommended texts for the exam syllabus, encouraging the students to read and analyse by using song lyrics and books that reflected their interests and culture. The class would often watch and discuss movies. She took them to an opera, a Christmas concert by a celebrated local choir, and an adaptation of the musical West Side Story.

Jacob’s commitment hasn’t flagged, even after the stabbing of her twenty-three-year-old son last year by a group of young men. He almost died, she says. Instead he suffered such severe wounds to his arm and face that he had to receive plastic surgery. Some of Jacob’s charges in YTC would have delivered similar agony — and worse — to other people’s lives. But the attack didn’t lessen Jacob’s will to teach these troubled youths. It strengthened it.

“My reaction was, these are the boys I have to target now,” she says. “These are the boys I have to understand better. I have to find some solution, academically, for that rage.” So Jacob has offered to teach additional classes — including A-level classes at YTC and an O-level English language class at the adult prison nearby — so that she can reach young men eighteen and older.

Action, she believes, eases uncertainty and fear. “When you can give like I gave, and teach and see results, you feel like you have control over something in society that seems uncontrollable,” she says. “You’re always feeling better if you’re doing something, rather than being a passive observer.”

Jamai Donaldson, who had attended a “prestige school” and already had two O-level passes before he fell into trouble, earned a grade one pass (the highest) through Jacob’s English language class at YTC. He also sat the human and social biology exam behind bars, earning another grade one, and the maths exam, earning a grade three. The last was remarkable, because the prison was not able to find him a maths teacher, so he had to cover the syllabus himself.

The majority of inmates at YTC require and receive primary-level education. Recruiting and keeping teachers for classes at the higher academic levels is a challenge. Many times a course will start and end after a semester, says Donaldson.“That’s why I kind of fell in love with Ms Jacob. She was consistent,” he explains. Jacob’s “straight talk” and advice, he adds, led him to do the three O-level subjects he needed to go on to the next level of education.

“I didn’t have the vision of how to pick back up the pieces of my life,” he says. “She helped give me the vision. Also, she was right there going through the process with me.”

But perhaps the most important thing Jacob did for her students was whet their appetite for reading. It provided wisdom and a diversion from situations that would have led to confrontation.

“It made me able to deal with them people inside there. It takes your mind away,” says Marc Friday, twenty-three, another of Jacob’s former students who’s out of prison and wants to be a writer, a skill he discovered he had in Jacob’s class.

“You can read and leave the place,” he says, “leave Earth if you want to.”