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Raoul Cantero's Supreme Detour

The first Hispanic justice on the state’s high court set out to be more Grisham than gavel-wielder

Photo by Craig Ambrosio

Published in 2023 Florida Super Lawyers magazine

By Carlos Harrison on June 21, 2023

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The first Hispanic justice on Florida’s Supreme Court didn’t set out to make history—at least, not in the legal arena.

“My ambition was to be a writer, a novelist, a sometime-guest on The Tonight Show.” That’s how Raoul Cantero put it in a bio for his undergraduate alma mater. On a recent spring day, he adds, “The last part was a joke, but the novelist part was absolutely true.”

 Getting a law degree was just a way to pay the bills until he made it as an author. The practice area was up in the air.

“I was thinking about something that would let me write,” he says, sitting in a glass-lined conference room 49 stories up in Miami’s skyline, overlooking the massive cruise ships lined up at the Port of Miami and the azure water of Biscayne Bay. “My third-year paper in law school was a novel,” he adds. “It was about a young lawyer who represented some low-income tenants in a housing project and discovered the fraud that was going on by the owners.”

His own office is crowded with memorabilia: a photograph of himself with U.S. Supreme Court Justice Antonin Scalia, another with Justice Samuel Alito; a signed championship game helmet given to him by his alma mater’s legendary football coach, Florida State University’s Bobby Bowden.

The John Grisham idea didn’t work out. The law, though, far exceeded his expectations.

Cantero became one of the youngest justices in state history when he joined Florida’s high court in 2002, at age 41. Now, having handled more than 450 appellate cases as an attorney—including 250 oral arguments in state and federal courts—he serves as managing partner of White & Case’s Miami office, overseeing 95 attorneys and heading the office’s disputes section.

Rodolfo Sorondo Jr., head of Holland & Knight’s appellate practice group in the Miami office, has known Cantero for more than 30 years and recently faced off against him in court. He says Cantero’s combination of intellect, knowledge and experience “makes him truly formidable.

“He has a view of the profession, and he has a view of litigation, from both sides of the podium, which adds considerable perspective,” Sorondo says. “So that it’s not just the question of making arguments that you feel are in your client’s best interests, but fashioning those arguments in such a way that an impartial and disinterested judge is going to find acceptable. That gives you a unique perspective.”

On this day, Cantero is remarkably relaxed and easygoing. He wears jeans on a Wednesday, topped off with a blazer; leans back comfortably in his seat. He’s quick to laugh, especially at himself.

When it’s suggested that Cantero might be the original Grisham, he erupts with, “Ha! Yeah, the one who didn’t sell.”

Nevertheless, Cantero attributes much of his success to his literary aspirations.

“All I know about legal writing I learned from my fiction-writing professor,” begins one of his Florida Bar articles. “Well, maybe not all of it; only everything that matters.”

Cantero had a tough-as-nails professor for whom he would write and rewrite—and rewrite again—his short stories, until every one of them got an A. That same article talks about the need for clarity, concision and revision in legal writing, but the big takeaways were “first, excellence does not come easy; it takes a lot of work. And second, it’s worth it.”

As long-lasting as its impact would be, Cantero’s passion for writing was itself a tangent. He went to FSU planning a career in the FBI, figuring a criminology degree was the best way to get there. He always planned on law school—“because you had to be either a lawyer or an accountant to go into the FBI at the time,” he says.

After a couple of lawyers told him he didn’t need a criminology degree to get into law school, Cantero switched to an English-business co-major, with co-minors in math and philosophy.

“It ended up being a four-year prep course for the LSAT,” he says.

It prepared him so well, in fact, that he got into Harvard Law School. But it also whetted his appetite for writing, and got him thinking about doing it full time.

“I actually applied for a summer internship at The Miami Herald,” he says. “But they denied me because they thought I really wasn’t serious about going into journalism.”

He was. While many of his classmates competed to get their articles into the Law Review, Cantero wrote for the Harvard Law Record, the affiliated, independent newspaper.

“It was more reporting,” he says. “I remember I did a feature article for the quarterly magazine that went to alumni on alternatives to legal practice—law school graduates who are in business, or just doing something else besides practicing law.”

Still, when he was offered a clerkship with a federal judge after graduation, he took it.

“First of all, it gave me another year to think about what I wanted to do,” he says. “And people would tell you back then, and they still tell you—and they’re right both times—that it’s a great experience to work for a judge. It’s a great start to your career. Especially if you worked for a good judge.”

His year with U.S. District Court Judge Edward Davis of the Southern District of Florida gave him a perspective that would shape his own judicial decision-making years later.

“What I liked about that experience was the objectivity that you brought to the legal issues,” Cantero says. “You weren’t advocating on either side. You were trying to figure out who was right. And so, sometimes it’s easier, sometimes it’s harder. Because sometimes figuring out the right solution or the right answer in law is difficult.”

When his clerkship ended, he got a Fulbright Scholarship and spent a year in Panama doing nothing but creative writing.

“So I’m still thinking, ‘Maybe I’m not a lawyer,’” he recalls.

But at the end of the year, the law seemed a surer way to put food on the table. His law school novel never found a publisher and, aside from a couple short stories, neither did anything else.

“We started having a family and I told myself, ‘I can be a writer and lawyer, a writer and a father, a lawyer and a father, but I can’t be all three,’” he says. “So I decided to be a lawyer and a father.”

Back in Miami, he got a call from a former partner at a firm where he had interned, who had started his own law firm. Cantero jumped at the chance to join, for a couple of reasons.

“First, it was kind of exciting to go to a firm that’s just starting,” he says. “Also, I would probably have more time to write than if I went somewhere else, you know? OK? I’m still thinking about that.”

Several of the new firm’s partners were former prosecutors. “And if you know anything about prosecutors, they love to stand up and argue and go to court,” Cantero says. “They hate to write. So, when an appeal would come up, they would give it to me. And I became the go-to guy for appeals.”

They came from each of the firm’s departments—commercial litigation, zoning, insurance defense, criminal. “I loved it,” Cantero says, “because it was a lot of writing. And that’s how I developed a specialty.”

Cantero joined the firm in 1988. “I was the 13th attorney. I was there for 14 years. By the time I left, we were 250.”

That was when Gov. Jeb Bush appointed Cantero to the state’s high court. It set off a media firestorm. Three things kept coming up in articles and editorials:

That Cantero was the grandson of Fulgencio Batista, the Cuban military dictator ousted by Fidel Castro.

That Cantero had once represented anti-Castro militant Orlando Bosch, a pediatrician-turned-counterrevolutionary implicated in dozens of plots against Cuba, and that Cantero had, in a Spanish-language interview, called Bosch “a patriot.” (Cantero says he was referring to Bosch’s activities in Cuba, not here.)

That Cantero, a devout Catholic, publicly called abortion “murder.” (He wrote a letter to the editor after an abortion provider’s murder, saying the action didn’t represent the attitudes of the movement, all of whom agree abortion kills children.)

Almost always, they led to the question of whether Cantero would be able to put his personal views aside on the bench. He dismisses those concerns.

“If anything, I think the governor was concerned that I wasn’t conservative enough,” says Cantero, who is an independent.

In one of the most widely publicized cases in state history, a battle ensued over a state law keeping Terri Schiavo alive over her husband’s objections. She had been in a vegetative state for 15 years, and her parents wanted to keep her alive. Cantero joined the other justices in striking down a law quickly passed by the Legislature to give Gov. Bush authority to deny the removal of her feeding tube. The Supreme Court decision allowed Schiavo’s feeding tube to be removed; she died shortly thereafter, in March 2005. The case sparked an international debate over the right to life versus the right to die, and who decides.

The Cantero and Bush families in a holiday photo: Gov. Jeb Bush (center), Cantero to his left, Bush’s wife Columba to his right; Ana Cantero to her right; the 3 Cantero children in front.

“Personally, it was very difficult,” Cantero says. “Legally, it was not that close of a call because it was pretty clear that what the Legislature had done was insert itself into a legal proceeding, which under the Constitution’s separation of powers you can’t do. So the outcome, I thought, was pretty clear. It was a unanimous decision, but personally it was very tough.” In fact, he attended mass in Miami the following Sunday, sitting toward the front, and the priest’s homily was about the case. “He was railing against the decision, and I crouched down in my seat, trying to remain anonymous,” Cantero recalls. “It was an awkward situation.”

In his time on the court, Cantero authored more than 100 opinions. He remained, throughout, willing to stand alone. One such case involved a class action over whether the validity of a contract had to be determined by a trial court before its arbitration provisions could be enforced. Cantero, the lone dissenter, argued that it was up to arbitrators, not the trial court, to decide the validity of provisions. Eventually, the U.S. Supreme Court sided with him, overturning the majority’s opinion. 

“His inner compass is very strong,” says former Florida Supreme Court Justice Barbara Pariente, who was chief justice while Cantero was there—and often on the opposing side of the court’s decisions. “Whether that’s driven by religion or his upbringing, whatever it is, it has contributed to make him the extraordinary jurist and lawyer that he is.”

Cantero has another appealing quality, Pariente adds. “[He] has a way of being persuasive but also, when he was a lawyer and I was on the court, he had a way of not becoming defensive about questions and also being able to kind of laugh at himself. That is unique in the legal profession.”

Cantero takes his seat on the Florida Supreme Court.

Cantero was born in Madrid to parents who had fled Cuba’s communist regime. They moved to Miami in 1961, when he was a baby. At his investiture, Cantero acknowledged the significance of being the first Hispanic justice to sit on the state’s high court: “Cuban Americans are exiles no longer. … From this day forward, our children know that they can aspire to any position in the state—indeed, in this country. One reason why I applied for this position was because I believed this was a goal worth achieving.”

Cantero in a favorite hat at age 3, in Miami.

Just six years into his tenure, though, a family health crisis brought Cantero’s time on the bench to an end. His daughter, then 12, had developed an adrenal gland tumor and needed surgery. Uprooted to Tallahassee, his family—including wife Ana and their three kids—had been missing their home and extended clan in Miami. Now they not only wanted, but needed, to be close again. Cantero resigned in 2008.

“It was pretty hard,” he says, but “we decided that it was time to come back.” (His daughter has since recovered.)

He quickly joined White & Case, handling, of course, appeals.

One case that stands out is something he calls his “pyrrhic defeat,” a loss that resulted in overwhelming victory. He argued before the state Supreme Court that his client, the chief executive of Suzuki Motor Corp., should not be forced to sit for a deposition in a products liability case because of the “apex doctrine,” which in many states exempts top company officers from having to answer in cases in which they don’t have direct knowledge of the matters at hand. Florida had no specific rule addressing the question at the time, except as it concerned some government officials, so the court denied Cantero’s motion. Barely eight months later, the state’s high court adopted a new rule recognizing the apex doctrine, and applied it to pending cases.

“So I lost the Suzuki case, but I really won because now I have a new apex doctrine,” he says. Since the case was still ongoing, Suzuki’s chairman never had to be deposed. In March, he notched a $32 million jury verdict on behalf of Trinidad and Tobago as second chair in a ruling 20 years in the making. “We inherited the case last April after the firm who carried it for 18 years suddenly got disqualified,” Cantero says of the case involving hyperinflated airport construction contracts. “So we had to digest 18 years of litigation in 10 months and, because of that, a lot of the witnesses had died or moved out of the county. It was exhausting, but after three and a half weeks of trial, we won.”

In 2014, Cantero took over as White & Case’s global partner for diversity. By the time he handed those reins to a successor five years later, the firm had launched a mentoring program to help minority students entering law school learn to navigate corporate culture. The firm also participates in the Miami-Dade Urban Debate League, which works with inner-city students, and supports a minority internship program in the federal courts.

“I think in the legal profession, especially in big law, the big gap is in Black lawyers—and especially Black partners,” Cantero says. “So I wanted to put an emphasis on recruiting, retaining and promoting Black lawyers, but also all kinds of minorities.”

In 2019, he became head of White & Case’s Miami office, and remains involved in his firm’s mentoring efforts.

“There are a lot of lawyers that are unsupervised. They don’t have the right training, they don’t have the right mentorship. So they get into ethical trouble,” he says. “Especially when lawyers are desperate, they’re on their own, they’re sole practitioners and they need to feed their families.”

While on the Supreme Court, Cantero pushed for a formal mentoring program for recent law school graduates in Florida. This year, the state Bar is introducing such an initiative, set to take effect this September, for new attorneys working in small or solo firms, or searching for jobs.

“Finally, I think they have noticed that there has to be something done,” Cantero says. “Mentorship is one part of the solution.” Another part, he says, is ensuring that the next generation of lawyers is as diverse as the society they represent.

“We’re making headway,” he says. “There’s still more work to do, but I think at least the law firms have realized that this is a really important issue.”

Members of Florida’s Supreme Court pause for a group photo in September 2008.

Field Days

Many are impressed by Raoul Cantero’s intellect, but few know of his athletic acumen. Back in 1979, he was a walk-on defensive back at FSU.

“I played a winter and the spring,” he says. “I played in the spring game.”

If his wife had her way, that would’ve been the extent of his gridiron career. But he went back to the field to play for fun—including flag football with other attorneys in the Cuban American Bar Association.

“That’s a league I still believe is secretly financed by the orthopedic surgeons of Dade County,” appellate attorney Rodolfo Sorondo Jr. quipped at Cantero’s Florida Supreme Court investiture.

“It is a tremendous source of business for them.”

Once, leaping up for a pass, Cantero came down hard and wrenched his back. It was excruciating, but he was more worried about his wife’s advice before he left for the game: “Don’t get hurt.” They had a wedding to attend that night. The first words out of his mouth, Cantero remembers, were, “Ani’s going to kill me.”

Cantero, #41, with the Christopher Columbus High School football team in 1977.

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