From the pews of Buffalo to the courtrooms of Pensacola, Aaron Watson built a life on purpose, prayer, and fierce advocacy. Now, with a thriving law firm, a growing family, and a citywide Juneteenth celebration, he’s proving what it means to bet on yourself and win.
Aaron Watson’s journey doesn’t begin in a courtroom; it begins with the early memories of church pews and snowy winters in Buffalo, New York, before his family relocated to Pensacola when he was a young boy.
"I remember the snow and the sermons," he says. "Church and snow, those are my earliest memories."
Raised by his single father, a pastor with a powerful presence, Aaron learned early what leadership, sacrifice, and love truly looked like. “He was my first superhero,” he says. “Watching him lead people and raise three kids on his own taught me that presence matters more than titles.”
In law school, Aaron struggled to find his place. “I thought I had to sound a certain way, use big words, fit a mold,” he recalls.
That changed the day he heard Willie Gary speak. Gary, an African American lawyer who owned two private jets called *The Wings of Justice*, made an unforgettable impression. “He pulled up in a Rolls-Royce, wore wooden Cartier glasses, an Italiano tie, and a Rolex,” Aaron remembers. “I’d never seen anything like it, especially not from someone who looked like me.”
After Gary’s talk, Aaron introduced himself. “I just wanted to shake his hand, but he invited me to dinner. Before the night was over, he offered me a job.”
“Willie showed me that law could be fruitful for the client and the lawyer. He gave me permission to be powerful.”
He also gave Aaron permission to embrace his roots. “He showed me it was okay to sound like my father to bring the preacher into the courtroom.”
Though Gary offered him a job, Aaron chose not to take it. “I had offers I could have gone to South Florida to work with Gary or joined a big firm that paid for my last semester,” he says. “But my dad was in Pensacola. My roots were here.”
Aaron went on to become a national trial advocacy champion. Determined to work with local legend Fred Levin, he sent a resume, followed by a bold move: he got a local paper to run a story about his national win and asked a friend to place it on Fred’s desk. It worked. Fred called him directly to offer a job.
Aaron would go on to try multimillion-dollar cases by Fred’s side. “Fred and Willie both came from nothing and built empires. They taught me that legacy isn’t about money, it’s about impact.”
After years of long hours and courtroom victories, Aaron made partner. But something didn’t feel right. “Two weeks later, I realized I didn’t own anything. I was still working someone else’s dream.”
That realization struck while visiting his father in the hospital. He turned to his wife, Kimberly and said, “I think God’s telling me to open my own law firm.”
He took the leap, and within days of launching his firm, Kimberly found out she was pregnant with twins. “I panicked,” Aaron says. “I thought, maybe I need to go back and work for Fred.”
But Kimberly looked him in the eyes and said, “I’m willing to go homeless with you if that’s what it takes.”
Three months later, they landed their first million-dollar settlement. “We didn’t think we could have kids,” Aaron says. “So to find out we were having two at once—it felt like confirmation from God. Double for our trouble.”
Kimberly has always been the firm’s co-visionary, handling everything from branding to billboards. That same spirit led her to create the Juneteenth Family Reunion, now the largest celebration of its kind in North Florida. “She got a call a month before the holiday and just said, ‘I can do it.’ And she did,” Aaron says. “She was having lunch with a city council member, sharing her dream of hosting a Juneteenth celebration. A few weeks later, she had vendors lined up, sponsors on board, and a full team in motion. People now travel from as far as New Orleans to be part of it. She didn’t just organize a festival, she created a community tradition that celebrates freedom, family, and faith.”
Aaron’s passion for justice runs deep. He recalls Jerry, a client who suffered a traumatic brain injury after a head-on collision. The insurance company offered $500,000. Aaron took it to trial. The jury returned a $12 million verdict.
After the win, Jerry handed him a hummingbird lapel pin that belonged to his mother. “I wear it in court to remind me who I’m fighting for.”
Aaron still prays with his clients before every trial. “Some battles are spiritual,” he says. “Faith has always been my edge.”
Now a father of three, including twin boys and his daughter, he sees time differently, especially since his father’s passing. “My son asks me, ‘Why are you staring at me?’ He doesn’t know I’m thinking about how fast it all goes.”
Even with a packed courtroom schedule, Aaron makes room for memories: pizza nights, bike rides, and superhero cartoons starring his kids. “I want them to remember that Dad was there.”
“The boys came up with this superhero series called The Thunder Twins, and their little sister Mia is the oracle who can see the future,” he laughs. “We used an AI script generator to turn it into a short film and watched it as a family. It was hilarious and unforgettable. I want my kids to know that whatever world they dream up, I’m in it with them.”
“In my profession, there is no peace,” he says. “There is more of a fight for the client. But my house is my peace. No arguing. It’s a safe place. We watched Beauty and the Beast the other night with the kids. That was awesome.”
“People see the suits, the cars, the billboards. But I’m still the same Aaron from Englewood Missionary Baptist, clapping on Sunday morning.”
“I’m a husband, a father, a son, a brother.”
Asked how he hopes to be remembered, Aaron doesn’t pause: “I hope they say I bet on myself and used everything I had to serve others.”
Aaron Watson’s story is a masterclass in faith, grit, and generational purpose. From courtroom victories to bedtime story time, bike rides, he shows what it means to lead with conviction and live with heart.
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“I hope they say I bet on myself and used everything I had to serve others.”
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“Double for our trouble.”
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“Some battles are spiritual. Faith has always been my edge.”
“I want my kids to know that whatever world they dream up, I’m in it with them.”
“People see the suits, the cars, the billboards. But I’m still the same Aaron from Englewood Missionary Baptist, clapping on Sunday morning.”