The 31-year-old lawyer, who honed his litigation chops at Miami Law's federal appellate clinic filing appeals for indigent defendants, represented the Miccosukee Tribe of Florida soon after graduation in the landmark case against AmerisourceBergen Drug Corporation, one of the three largest U.S. drug distributors of opioids. But both his name and the case are pieces in his origin story.
Redemption road to Miami Law
An ocean lay between the then-college dropout and now attorney. It took Osceola's arrest and the death of his cousin and Bird Clan brother, the Seminole bull rider Garrett Anderson, from an overdose of opioids, to bring Osceola to his call to Jesus moment. He began to formulate a plan that would see him as a lawyer within a decade.
"That life seems like someone else's now," said Osceola, J.D. '18, from his office at the Miami-Dade Public Defender's Office, where he is an assistant public defender and the first of the Miccosukee tribe to graduate from law school. "Where I came from is part of who I am. Becoming an attorney and arguing every day is still rooted a little in that rebellious teenager. The need to be heard survived, but now is refined and targeted."
Growing up, the then tribal chairman of the 500-member Miccosukee Tribe, Sonny Billie, had lofty expectations of the cousins. He implored other children to look to the bright stars of Osceola, who bears the name of the great war chief, and Anderson and emulate them. But somewhere in the intervening years, both boys lost their way. Anderson had even called Osceola a few months before his death, urging him to put his life back on the track of his destiny and go back to college. Of the boys Osceola grew up with fishing and playing video games on the 713-acre reservation in the heart of the Everglades, three are dead from overdoses.
Soon after, Osceola started working at the tribal health clinic and enrolled in business school at Nova Southeastern University, staying until his grades were strong enough to transfer to the University of Miami. Throughout his pre-Miami Law years, Osceola would rise to Billie's challenge, taking on more extensive and more prominent roles in tribal leadership. He would head a business development project in Overtown, helping local companies improve accounting, sales, and marketing practices, taking his knowledge to the tribe's mega Miccosukee Resort & Gaming facility on Krome Avenue.
Osceola would save the tribe millions by tightening up on inefficacies and uncovering and correcting fraud and corruption within the organization. He assumed leadership of the slots, the tribe's largest operational group, a position he held throughout his first semester of law school when it became apparent that he could not serve two missions with the success he expected of himself.
"I came to Miami Law because I wanted to be able to do more for the tribe," Osceola said. "Business is a base, but knowing the legal system is an even more valuable asset, understanding how state and federal courts work and how government works. Both are so intertwined with the law that I thought I would get that exposure, which I did in a very visceral sense.
"I gravitated early on to take the most challenging courses. While so much of being a young attorney is having the grades to get the good jobs, I focused on taking the most demanding courses because I wanted to have a broader grasp of law – a little about everything. Professors like Kunal Parker, Ricardo Bascuas, and William Blatt take their roles very seriously, but I did not have a bad instructor the whole time."
Diverse student body expands horizons
Osceola said that an unforeseen benefit he received at Miami Law was exposure to a very diverse student body. "I've made lifetime connections with students from everywhere, and it changes the way that you view the law because it isn't just black and white and we are all just navigating through it, and the University of Miami School of Law prepares you for that, but it also prepares you for the uncertainty of law."
At the law school, Osceola interned with Judge Wolski at the U.S. Court of Federal Claims in Washington, D.C., during the first year of the Trump administration, "when D.C. was definitely in a period of change." He also served as Professor Sergio Campos's research assistant and interned at the offices of storied Miami litigator and adjunct professor Adam Moskowitz, J.D. '93.
“I first met Curtis when he was a student of mine in my advanced civil procedure II class,” said Campos. “The class was filled with superstars, but Curtis by far shined the brightest. At some point late in the semester I stopped calling on students and simply asked Curtis for the answer, and he always gave the correct one.
“After teaching him I immediately asked Curtis to be my research assistant. Having Curtis as a research assistant was like having a second professor around to bounce ideas. He is one of the very best students I have ever had,” Campos said.
Osceola would stay with The Moskowitz Law Firm post-graduation working on the opioid case and doing pro bono work providing legal services to homeless drug addicts. "In 25 years of practicing law, I've never seen a young attorney have such passion and dedication towards a cause as he does," Moskowitz told the Daily Business Review in a 2019 profile of Osceola. "I think someday he may even be the head of his tribe."
Future in championing for his tribe
His move to the public defender's office gave the young attorney exposure to the at-large Miami community and he now represents indigent defendants through to trial, another steppingstone to his road back to the Miccosukee Tribe, and a rise to leadership. He is also involved in working with both the tribe and his alma maters to mentor tribal children to pursue paths in higher education to build the tribe's authority and lessen reliance on outside business leadership.
"To build and succeed, we have to have more indigenous students educated in many different fields to protect and sustain the sovereign rights of the tribe," he said. "It's not just about being lawyers and figuring out the law because a lot of times the law is often construed against the tribe; we need people who are going to be politicians and scientists and people who are problem solvers, who can work on behalf of the tribe."
Leading a new generation of tribal leadership is part of Osceola's next decennium plan. He recently ran for treasurer of the tribe and, though unsuccessful, will run again in the fall of 2021.
"I think I have a lot to give with my business experience and my law experience," he said. "I think I could be valuable to the tribe as a councilman. I see my future with the tribe in a leadership capacity, whether in the administration or as an attorney very soon, and further out working on behalf of the tribe in Tallahassee and Washington."
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