Caldwell Huckabay seemed to have it all – a thriving practice at a prestigious law firm, distinguished clients and colleagues with whom he enjoyed working.
Except he didn’t have it all. But the day would come when he would.
As far back as Huckabay could remember, he’d wanted to be a lawyer. A great uncle he’d never known had been an attorney and judge in Baton Rouge, and the stories his family told about the man took root in his mind and steered him toward the law.
Every step forward in life took Huckabay closer to that point. As an undergraduate at “Tiger Tech” (Louisiana State University), Huckabay majored in history – partly out of a love for the subject but also because he says he believed it would dovetail nicely into law school.
A Louisiana native, Huckabay stayed at LSU for law school. During breaks in classes, he clerked in Chattanooga so he could see his parents. The time he spent in the city took root in his heart and steered him toward a new home.
So far, so good. But Huckabay took a wrong turn out after graduating from law school in 1989 when he took a construction litigation job at Chambliss Bahner. There were no problems with the firm, his practice or his colleagues, he says. But there was a disconnect within him. Throughout law school, Huckabay had aimed to become a trial attorney. Still inspired by the stories about his great uncle, he saw himself advocating for things greater than himself.
Huckabay’s father, an Episcopal priest, had also had a profound impact on him growing up. Huckabay didn’t want to just practice law; he wanted to help the community in which he was living.
“I took the job at Chambliss for the wrong reasons,” he acknowledges, alluding to the financial security that comes with a successful practice at a well-known firm. “And it wasn’t a good fit for me. I’m not much of a business person and I’m not interested in becoming one.
“Also, I didn’t feel like I was making a difference in the community; I felt like I was just makin’ a livin’.”
Huckabay gave construction litigation the college try for seven years before rebooting his career by becoming a prosecutor for the district attorney’s office in Hamilton County. For the first time since becoming a lawyer, Huckabay felt like he and his job were a good match.
“My dad used to say you need to enjoy what you’re doing for a living because that’s what you’re going to spend most of your time doing,” he points out.
When Huckabay’s boss, then District Attorney General Bill Cox, ran for re-election, Huckabay supported his trial partner, Lee Davis, instead. When Davis lost, Cox let Huckabay go.
“Bill’s a good dude,” Huckabay says. “I would have fired me, too.”
Huckabay’s professional crisis was compounded by a personal one: he and his wife had separated. So, at 35 years old, and with a career, a wife and three kids hanging in the balance, Huckabay asked himself the question most people tackle at a younger age:
What do I want to be? He then spent a year trying to answer that question.
“I believe if we’re open to our calling, it will reveal itself,” he adds. “So, I kept trying to be open but nothing was coming to me.”
Huckabay had been tossing around the idea of teaching but getting his foot in a door – any door – wasn’t easy. Finally, Red Bank Elementary School hired him to teach a self-contained fourth-grade class.
Since Huckabay didn’t have a certificate to teach, he taught on a permit, which he was able to renew only twice. Returning to college to earn the remaining 54 credits he needed to become certified wasn’t an option, so he started looking at schools that didn’t require a certificate. “I interviewed at all the private schools,” he recalls, “and then I started hounding them.”
Huckabay was driving home from his grandmother’s funeral 16 years ago when O.J. Morgan, now head of The Bright School, called and offered him a job at Baylor School, a private, coeducational prep school on the outskirts of Chattanooga. Huckabay was thrilled.
From there, his story takes a permanent upturn. Huckabay taught sixth grade humanities for six years and then moved to the upper school to teach world history and an introduction to law class. In addition to covering subjects that are close to his heart, he’s developed his own course: an elective for seniors on ancient Rome.
“Teaching seniors is a blast. I like their maturity level and sense of humor,” Huckabay says.
Huckabay is now a veteran teacher who’s just one year shy of his 20th anniversary in the profession. In addition to doubling the amount of time he practiced law, Huckabay is celebrating new anniversaries with his wife, with whom he reconciled, way back when.
Although Huckabay is “makin’ a livin’” as a teacher, he’s also making a difference in his community.
“The ability to spend time with high school students, who are at an impressionable age, and guide them in a positive direction is hard to beat and a lot of fun. I get more than a paycheck from this job. Just to be a part of these kids’ lives is special,” he says.
Although Huckabay’s days as an attorney are long behind him, some of the skills he learned during that phase of his life are still with him and serving him well.
“Teaching is like dealing with a jury,” he adds. “You have to read your class and find ways to persuade them to pay attention or stay engaged.”
Huckabay doesn’t regret his days in the legal profession. He even says he’d consider returning to it someday for the right job. “I’m going to teach as long as I enjoy it, and when that changes, I’m going to do something else,” he says. “If I did go back to the law, it would be along the lines of the DA position.”
For now, though, Huckabay is more than content with where he is and what he’s doing. He also relishes the time he has to enjoy life in the city he grew to love during a summer clerkship many years ago. With his three kids grown, he’s returned to gardening, and he and his wife take frequent rides on the River Walk on their recently purchased couples bike.
Still, there’s a part of him that remembers the stories about his great uncle and dreaming of advocating for something greater than himself.
“I miss prosecuting. It’s hard on you. You see people at their worst. But it was satisfying to be part of the mechanism that was keeping our community safe,” he says. “I’d love to go back and try a murder.”