Featured Alumnus: James W. Jennings ’99 | Avon Old Farms News | About Us | Avon Old Farms

As is the case with every featured alumnus, the following article will give Avonians and their networks a brief synopsis of the subject’s time as a student and what they’ve been up to since graduating. A short collection of paragraphs could never encapsulate all that has occurred across multiple decades of someone’s life, but instead gives readers a small insight into who their friend or brother has become. Luckily, in the case of this month’s featured alumnus, James W. Jennings ’99 has written a much more detailed and complete composite of his life thus far, and anyone interested can read the full story in his book — in his own words.

That book, entitled Wings of Red, was published in 2023 by Penguin Random House, and is a semi-autobiographical tale of James’s life. The story follows a homeless substitute teacher in New York City who dreams of becoming a writer. He endures hardships and overcomes conflicts to ultimately realize that mentoring and teaching could be a path forward for him. It has received positive reviews from notable sources including the New York Times Book Review who felt the protagonist of the book “navigates his circumstances and city life with grit and grace.”

The story in Wings of Red is one that James felt he had to tell. This was something he says he realized during his time at Avon Old Farms. James grew up in the north end of Hartford and was at risk of going down a bad path. He was being bred for gangs and frequently skipped school. Despite all of this, he was still doing his best in a bad situation. His grandmothers instilled in him the value of education, so when he had the chance to apply for admission to Avon Old Farms, he jumped at the opportunity. James puts it very bluntly, “Avon saved my life.” Unfortunately, this couldn’t be the case for some of his friends.

It was the death of his childhood friend Timothy — a role model for James who originally introduced him to the arts — that made James realize he had a story he needed to tell. “It was my sophomore year, and I got a call from my grandma telling me that Timothy had been shot to death in New Haven. I remember the monitor in my dorm, a guy named Steve, answered the call. That was part of the monitors’ job back then. I could just see his face, the way he was reacting, I realized that this wasn’t a normal situation. I realized the impact this story could have. That’s the role of the writer in society. If it’s a powerful story, someone has to tell it.”

Dealing with the loss of a close friend wasn’t the only struggle James had to overcome in his first few months at Avon. He says the grades didn’t come easy at first, but after working at it, he was named to the Honor Roll his sophomore year, Dean’s List his junior year, and Headmaster’s List as a senior.

“It’s tough because Avon is pretty competitive, but I knew I had it in me. I take pride in working hard and figuring things out.”

In fact, James excelled in all areas at Avon, not just academics. He played a sport every season but was a crucial member of the varsity basketball team. He wrote for the Avon Record and Hippocrene, as well as served on the yearbook staff. He also was the leader of the social activities club, organizing dances and other events for his classmates. He even received the Order of Old Farms at his graduation. However, what he is likely most remembered for is his impressive work in the art studio. “I was always a creative. Once I started taking AP art classes, I just lived in the art studio.”

Additionally, the Avon Old Farms campus is where James wrote his first book. His senior year he committed to writing 2000 words a day. He went to the computer lab every day to complete this self-appointed task. He says that story has since been sitting in a shoe box until he wants to revisit it, but it gave him the important first experience of writing a full body of work. He enjoyed it as well, and began working on other writing projects including a self-published book titled United Strays of America.

After graduating from Avon, James went on to attend Emory University where he played basketball and studied English literature. He attended Brooklyn College for his master’s. James would then spend the next several years on a “fantastic voyage of really high highs to bone and soul-crushing rock bottom.” He taught, tutored, or coached in several different schools throughout New England and New York City. While his role as a coach and mentor for children remained a constant, his living situation was often in flux. It was during this time he wrote Wings of Red.

“I was literally writing it as I was living it,” he says.

Although the book was completed around 2010, it wasn’t published until recently because James wanted to make sure he got the most out of his contract. James explains; “With regards to publishing Wings, it was a matter of equity and ownership. I knew I couldn’t allow my life’s work to be owned by someone else. It wouldn’t sit right with my ancestors or the people looking up to me. Not when I had the opportunity to speak my truth and stand up for what’s right, regardless of how it’s been. So, I took the risk and asked for what I deserved. I also assumed costs as well so I had full skin in the game in our equity partnership.” In the end, with assistance from Soft Skull Press, James got the deal he was after, and is now in the works of publishing a second book.

Outside of writing, James continues to be a mentor for thousands of kids. Known primarily to many as “Coach,” James says he dedicates his writing to his mentees and fellow educators. He continues to coach and teach while working hard promoting his published work. He says he enjoys the marketing side of things as well. “I get invited to talk to book clubs, youth groups, etc. to talk about my book. I love talking about literature. If I can pair that with some self-promotion, it’s perfect,” James says. In 2016, he founded 49th Hour Workshop, a non-profit arthouse space that assists aspiring creatives with publishing, consulting, workshops, projects, artist residencies, and non-profit partnerships.

He remains involved at Avon as well. James co-founded and maintains a scholarship at Avon, and has often contributed time and effort to the Avon African American Alumni Association (A5). James was back on campus this past fall for his 25-year class reunion. “It was amazing being back. Avon itself — the natural area — you feel very lucky to be there. Then you add the school’s history into the mix, it’s incredible.

To learn more about James’s writing and non-writing endeavors, you can visit 49thhour.com.

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