Double ’Canes Journey from UM Undergrad to Miami Law to Giving Back

Double ’Canes Journey from UM Undergrad to Miami Law to Giving Back

Roy Black, B.S. '67, J.D. '70, Jerry Hollo, A.B. '90, J.D. '93, and Ana VeigaMilton, B.S.E.E. '87, J.D. '93
Roy Black, B.S. '67, J.D. '70, Jerry Hollo, A.B. '90, J.D. '93, and Ana VeigaMilton, B.S.E.E. '87, J.D. '93

Roy Black, Jerry Hollo, and Ana VeigaMilton enrolled at the University of Miami for very different reasons: Black wanted to be an oceanographer, Hollo missed the warm weather, and VeigaMilton knew there was no way a Cuban girl could convince her parents to leave Miami.

Yet all three joined an exclusive group: double ’Canes, who graduated from the U undergrad and Miami Law. In the decades since, they’ve remained fans of and advocates for the U, they’ve sent their children there, and each of them, in their own ways, has continued giving their time, talent, and resources to the University of Miami.

“I attribute the growth of Miami not as a party place, but as a real city of substance, partly to the growth of the University of Miami,” VeigaMilton said. “I am an ambassador of the university, and I’m thrilled that my family and I can be a part of it.”

From Jamaica to Juries

Black, B.S. ’67, J.D. ’70, who has become one of the most high-profile defense attorneys in the country, started his journey at the University of Miami with dreams of the ocean. His stepfather was British and moved the family from Jamaica to the Bahamas when Black was a boy, exposing him to island life.

“I did a lot of ocean swimming, so I thought I wanted to go into oceanography,” he said.

He started as a chemistry major at the U, taking classes in what was then known as the North Campus (now the Coral Gables Library). But he changed course when he took a series of government classes (now called political science). He loved doing research and writing about a wide variety of subjects. And then, when deciding what to do after receiving his bachelor’s degree, he recalled another lesson he learned in the islands.

Black had a math teacher in Jamaica who had it out for him. “Either because I was white or I was American, or possibly because of both,” he said. The teacher constantly picked on Black, ordering him to the blackboard to solve equations based on English currencies like pounds, shillings, and pence.

“He did it so he could embarrass me,” Black said. “That drove me crazy. I grew to hate petty authority. That generated my interest in going into the law, into becoming a public interest lawyer, a public defender.”

So, Black applied to the University of Miami School of Law and was accepted the next day. While there, he grew to love and hate one class in particular: a contracts class taught by the legendary Professor Richard Hausler, a 52-year veteran of the school who specialized in the Socratic Method.

“You would sit there on the edge of your seat praying, ‘Don’t call me,’” Black said. “But it was the greatest education because you had to be prepared, you had to know the subject matter intimately, you had to be able to articulate it, you had to work under pressure, you had to be able to answer his questions. He was one of those once-in-a-lifetime professors…that makes an indelible mark on you.”

After graduating, Black went straight to work at the Miami-Dade County Public Defender’s Office. From there, he built a career defending some of the most controversial defendants in recent memory, including Jeffrey Epstein, Rush Limbaugh, William Kennedy Smith, and a long list of serial killers, drug traffickers, and billionaires facing all kinds of charges. Black says he’s taken on those cases because of the lessons he learned in Jamaica and later as a public defender representing primarily Black and Hispanic people.

“You get into that kind of thinking where it’s you and your client against the world, against the state, and later on, against the federal government,” he said. “It’s a mindset one adopts to survive.”

The other constant throughout his career has been the classes he teaches at Miami Law. Three years after graduating, he started teaching a workshop focused on federal evidentiary rules. That has morphed into a training course on how to argue at trial, running his students through mock witness examinations and exchanges with a judge. Black said that’s his favorite way of giving back to the school that launched his career.

“I really enjoy teaching it,” he said. “You get these very bright kids in there, so I’m trying to pass it on to the next generation.”

Real Estate in His Blood

The road to the University of Miami differed slightly for Hollo, A.B. ’90, J.D. ’93.

As the son of real estate mogul Tibor Hollo, who founded Florida East Coast Realty and built many of Miami’s most iconic buildings, Jerry Hollo always knew he wanted to be part of that legacy. But he wanted to get his education and earn his keep to contribute and grow the family business.

At first, that quest took him north. After growing up in Miami Beach, Hollo wanted to explore another part of the country, so he started at George Washington University. He loved the school and the energy of living in Washington, D.C., but he soon grew tired of going to school in the crowded capital city, so he transferred back home and started at the University of Miami. “There is no campus at GW. It’s a true city school,” he said. “To have that campus at UM was a much different experience.”

His school finally decided, Hollo dug into the work. He realized early on that he wanted to attend law school, so he picked a major that he thought would translate well: philosophy. “It requires you to do a lot of writing and critical thinking,” he said. After earning his bachelor’s degree in 1990, he entered Miami Law.

As a law student, Hollo interned for U.S. District Judge James Lawrence King during a hectic period. Federal agents arrested five judges for corruption in “Operation Court Broom,” and Judge King oversaw some of the cases. “I wanted an opportunity to see different things, so it was an incredible time to be working with him,” Hollo said.

But for most of his time at Miami Law, Hollo crafted a unique schedule where he worked at the family business while attending school simultaneously. He’d spend at least 15 hours a week at Florida East Coast Realty learning about construction, acquisitions, and property management and then spend the rest of his time attending class, studying, and writing his papers. “Essentially, I created my own LL.M. development program,” he said.

That combination of development work and legal education allowed Hollo to visualize a deal from all sides.

“You need to understand where you can get caught in quicksand,” he said. “[Classes at Miami Law] taught me to look around the corners on deals and contractual issues.”

After graduating from Miami Law, Hollo worked at a transactional firm for a few years before finally going full-time at Florida East Coast Realty. He now serves as co-CEO with his brother, Wayne Hollo, and has helped guide the company as it continues expanding and remaking Miami’s skyline.

And all the while, he’s continued helping his alma mater. Hollo serves on the School of Law’s Robert Traurig-Greenberg Traurig Real Property Development LL.M. Advisory Board, his family’s company is a sponsor of the school’s annual Real Estate Impact Conference, and Hollo continues spreading the gospel of the University of Miami to anyone who will listen.

“The university is really well-positioned,” he said. “I get calls from people all over the country asking if I can help get their kids into the school. It’s like nothing I’ve ever seen before. We need to build on that.”

Gem in the Community

VeigaMilton, B.S.E.E. ’87, J.D. ’93, briefly considered going away for college.

Her family left Cuba when she was a baby and eventually settled in Miami, where VeigaMilton excelled at Southwest Miami Senior High. She earned the highest GPA in Miami-Dade County (5.3) and got a partial scholarship to Duke University, but when she imagined telling her parents, she knew what to expect. “Tears of sadness,” she said.

So VeigaMilton set her sights on the University of Miami and earned the Isaac Bashevis Singer Scholarship—one of the premier scholarships awarded to exceptional and academically accomplished high school seniors. At first, she followed in the footsteps of her father, who spent his career as a telecommunications engineer in Cuba, Spain, New Jersey, and South Florida. VeigaMilton studied electrical and computer engineering and became very involved on campus, joining several honor societies and the Society of Women Engineers. She helped organize social events for the reclusive engineering students. “The girls ruled the school,” she said with a laugh. “It was a great experience for me.”

After graduating in three years, she started working for BellSouth as a strategic planner in the company’s Fort Lauderdale office and later on the operations side in Miami. However, she found her education lacked rhetoric and language arts and yearned to return to school. She was interested in something other than the business degrees most people gravitated toward during the economic boom of the late ’80s.

Instead, she was determined to go to law school, was accepted at Miami Law with a full Dean’s Merit Scholarship, and was thrilled when she realized that her engineering education, which was filled with analysis and problem-solving, was perfect preparation for law school. “The logic is exactly the same, but you use your words instead of numbers to make your argument,” she said.

VeigaMilton married just before law school and gave birth to her first son in early 1993 as a 3L. She had the option to postpone graduation until winter, but VeigaMilton pushed through, graduating on time, summa cum laude. She was honestly too exhausted to study for the Florida Bar exam. Still, she passed on her first try, a feat she credits to her Florida constitutional law class.

After becoming a member of the Florida Bar, she practiced family law, taking pro bono cases. But she has since joined the leadership of the business started by her father-in-law—United Property Management—and presides over the charitable organization created in his name—the José Milton Foundation. She has also become involved in various nonprofits, including the South Florida Red Cross, United Way Miami, Jackson Health Foundation, and Zoo Miami. She is a past president of the University of Miami Citizens Board and is on the board of trustees, currently chairing the Academic Affairs Committee. “I look for gems in the community that help elevate Miami,” she said.

At the University of Miami, she created a scholarship that marries her two educational loves: science and the law. The Ana VeigaMilton and Diana Milton Endowed Tech Law Scholarship is also named after her daughter, who completed her undergraduate degree at Georgia Tech and graduated from Miami Law in 2023. Her engagement with the University of Miami, VeigaMilton said, is her way of giving back after she received so much scholarship money to attend the University and Miami Law.

“I was on the receiving end of philanthropy, and that’s why philanthropy is so important to me, to help a stranger on their path—to help catapult someone’s future,” she said.

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