Raquel Regalado Took On the Establishment; Now She Wants to Run It

Regalado on the set of her weekly TV show, Esta Semana con Raquel.
Regalado on the set of her weekly TV show, Esta Semana con Raquel.
Photo by Marta Xochilt Perez

The Spanish-language radio station La Poderosa (670 AM) broadcasts from a large, square concrete-and-glass building on SW 27th Avenue in Little Havana. The building's cafeteria, Bocadito Express, is a poorly lit, one-room blue-collar spot on the ground floor where area workers drop in for cafecitos and medianoche sandwiches.

Raquel Regalado walks in wearing an elegant beige dress suit, tall brown leather boots, and a Louis Vuitton scarf around her neck. With her long auburn hair and porcelain features, she could be a European actress. But the man behind the counter doesn't glance twice -- Regalado is a regular.

In heavily Cuban-accented Spanish, she orders two croquetas, which the café worker loads from behind the warm glass onto a small plate. Regalado then promptly heads for a seat at the back of the room.

Between bites, over a man's shouting on the phone about the price of an apartment rental, she muses about her weekday Spanish-language radio show, Las Dos Caras de la Noticia -- "The Two Faces of News." Through that show and her weekly TV program, Esta Semana con Raquel, she has cultivated a devoted following that includes thousands of Cuban-Americans who know her as Raquelita, the convivial daughter of Miami's mayor, Tomás Regalado.

She says she loves working in media, that it feels like home. But then the second-term Miami-Dade County school board member adds she might soon give it all up.

"When you become mayor, you have to leave it behind," she says matter-of-factly. "I'll give up radio and TV. Both."

The 40-year-old recently announced she plans to run for either city or county mayor. Neither position has ever been held by a woman. And even though the elections are still one and two years away, respectively, she's the odds-on favorite for both. Her political profile is higher than ever. Last fall, Regalado, an Energizer Bunny single mom of an autistic 11-year-old daughter, put her reputation on the line to almost single-handedly bring down a controversial $393 million courthouse bond.

"I don't see how this woman can be stopped," Miami Herald columnist and political observer Joe Cardona says. "She's got a... good chance to become the first female mayor. I don't think [Miami-Dade Mayor] Carlos Gimenez's place is enviable right now."


Early in the morning of March 10, 1990, a pencil-thin 15-year-old woke up and carefully positioned a blue bow in her hair to match her Catholic school uniform. Then Raquelita Regalado headed out to take on America's most powerful Cuban exile.

Jorge Mas Canosa, the notoriously fiery Cuban American National Foundation chief and adviser to numerous presidents, was debating a Soviet official at the Hyatt Regency in downtown Miami. With his trademark passion, Mas Canosa torched his opponent and talk

ed about the future of Cuba. After the talk, there was a question-and-answer session.

"Mr. Mas Canosa," began the teenaged Raquelita, then a student at Our Lady of Lourdes Academy, "with all due respect... you don't represent all Cubans."

The next day, her bold challenge -- along with her picture -- was featured in the Miami Herald. Her mom, also named Raquel, dragged her to local Spanish radio stations to give interviews explaining her comments. Raquelita's career as a media darling had officially begun.

Considering her family, the audaciousness wasn't a surprise. Tomás Regalado Molina, Raquelita's paternal grandfather, was the president of a Cuban journalists' organization. After the 1959 revolution, he was jailed as a political prisoner, and in 1962 his 14-year-old son, Tomás, along with Tomás' younger brother, Marcos, was shipped to South Florida as part of the famous Pedro Pan visa waiver program for Cuban children 16 and younger.

The younger Tomás, long before he was elected Miami's mayor, grew up to become a prominent Spanish-language radio and TV journalist, reporting from around the world and serving as the first Cuban-American member of the White House Press Corps. Still in his early 20s, the cool, even-tempered Tomás was chosen to cohost a four-hour Saturday-night music variety show, Sábados Musicales.

His cohost was another young Cuban exile, the beautiful, sharp-tongued Raquel Ferreiro. The two quickly fell in love and then married in 1972. Their first son, Tomás Napoleon, was born the next year; Raquelita arrived less than 12 months later; and another son, Jose Francisco, came in 1985.

The family was close-knit and talkative. Raquelita quickly learned that she "had to fight for airspace" in vigorous family debates, she says, and she got along well with her outgoing, sociable older brother.

She was also exceptionally stubborn. When she was 7, she didn't like red beans, and she'd refuse to eat them at the dinner table. Her mom would then prohibit her from getting up to watch television or even do her homework. Raquelita would sit alone at the table, locked in a battle of wills with her legendarily feisty mother. "I would say to my wife: 'Come on, the girl doesn't want to eat it,'" Tomás Regalado recalls.

But the elder Raquel would reply that their daughter "has to learn," and the standoffs would continue for three or four hours, until the parents had no choice but to put their daughter to bed.

She peppered Reno with questions about getting her job. "Do I have to be as tall as you?" Raquelita asked.

When she wasn't at school, Raquelita was at La Cadena Azul, the Spanish-language radio station where her parents worked, along with her grandfather after he was freed. "I always joke with people that my parents were huge proponents of child labor," Raquelita says. "My older brother and I, we would do the boards, and we did the sound effects, we did the commercials. Because why would you hire somebody if you had two kids running around, right?"

 

As a new school board member, Regalado's first major victory was securing funding for a new playground at Citrus Grove Elementary.
As a new school board member, Regalado's first major victory was securing funding for a new playground at Citrus Grove Elementary.
Photo by Marta Xochilt Perez

At the age of 4, the precocious Raquelita began recording kids' roles in commercials. At the radio station, she also met the various giants of Florida politics who were her parents' guests: Lawton Chiles, Dante Fascell, Bob Graham.

But no one made an impression quite like Janet Reno. It was while Raquelita sat in the station listening to her mom interview the Miami native and then-U.S. attorney general that the then-7-year-old realized women could hold political office. Once the interview finished, she rushed to stop Reno in the station's elevator and peppered her with questions about how it was possible that a woman could be chosen for that job. "Do I have to be as tall as you?" Raquelita asked.

In school, young Raquel was a perfectionist. "She would come and cry if she got a 99," her dad says. By eighth grade, her last year at Sts. Peter and Paul Catholic School, she was tall, slim, and pretty. But she never spent time passing notes to boys or drawing cutesy hearts like most of the other girls. She was the leader who always made friends with even the shiest kids. But she was also seemingly on a different level, more interested in debating global politics than gossiping about boys. "She was like a little adult," says Esperanza Martinez, Raquelita's middle-school social studies teacher, "a little girl, but incredibly articulate."

The elder Raquel Regalado, intent on turning her daughter into a performer, enrolled her in ballet, flamenco, and acting classes. She also regularly told her she could be "either a hammer or a nail," so she might as well be a hammer. Raquelita, whose ambition and confidence were already strong, learned the lesson well. Martinez remembers that during a lesson on the federal government's three branches, her star student announced, unprompted, that one day she would be president. "Everyone turned around," Martinez recalls. But none of the students sneered. "I looked at her and I knew. I said, 'You know what? I think this kid can do it.'"

A few years later, Raquelita was offered an internship with Democratic political legend Bob Graham, then a U.S. senator. For two high-school summers, she tagged along as Graham carried out his famous "workdays" campaign, trying out the lives of various workers in an effort to better understand the public he served. For Regalado, who now considers herself a moderate Republican, the impact was monumental. "Years later," she says, when she was running for school board and asked about a childhood hero, "my father was heartbroken when I said Bob Graham."


The elder Raquel Regalado was a giant in the South Florida Cuban community. In addition to her two immensely popular radio call-in politics shows, Lo Que Otros No Dicen ("What Others Won't Say") and Panorama, she was renowned as a political voice and journalist, as well as a human rights advocate -- for years she attended the United Nations Human Rights Commission in Geneva.

But in January 2008, when she was 60 years old, Raquel came down with food poisoning. The illness, caused by a bacterial infection in her liver, unexpectedly worsened, and she was placed on dialysis. She then had a heart attack, and doctors decided she required open-heart surgery. If her mom had made it through the first 24 hours, her daughter recalls with a heavy voice, the doctors said she'd be fine. "She died at 23 and a quarter." It was less than a month after she had gotten sick.

"Everyone was in shock," Raquelita says. "My mother was such a dynamic human being... the type of person you never really think about being without." But after her death, with the family's center suddenly gone, the daughter sprang into action. She helped organize the funeral, which was widely covered by the media and attended by a thousand people. Then, with her father still in shock, she took on the task of combing through her mother's belongings and redesigning the family home for her father and younger brother. She didn't have a chance to grieve until months later and instinctively dialed her mom's cell phone for more than a year.

But the tragedy didn't end there. Her marriage to Frank Herrera, her husband of seven years (they met when he sat next to her in law school at St. Thomas University), was disintegrating. She later learned he was having an affair. "We won't get into the specifics of that," she said in a 2012 deposition, "but let's just say that when my mother was having open-heart surgery, he was skiing in Colorado because he really needed to get away. So I bury my mother, he doesn't make it back in time. That's always telling, right?"

Just a few weeks after his wife's sudden death, Tomás, by then a longtime city commissioner, announced he would run for mayor of Miami. It was what his wife would have wanted, he said, and his daughter would run the campaign. "She didn't say, 'I want to run your campaign,'" Tomás says. "She said, 'I'm going to run your campaign.'"

Raquelita had long been involved with her father's politics -- when he ran his first city commission race, she served as an unpaid chief of staff -- but now she was stepping into the role her mother had always played, as his chief strategist and campaign treasurer.

She quickly proved an astute manager, coordinating a hectic campaign headquarters and helping shore up a large fundraising advantage. In November 2009, Tomás won easily, beating fellow Commissioner Joe Sanchez by more than 40 points. But two years later, both father and daughter were investigated for possible corruption. The campaign's contribution and expense reports showed a $40,000 discrepancy, and the Regalados had turned in at least one filing past deadline. The Miami-Dade State Attorney's Office, Florida Department of Law Enforcement, and Miami-Dade Commission on Ethics and Public Trust launched a joint probe. Eventually, they ruled the errors were attributable to honest mistakes -- two family friends had mostly kept the books, with Raquel and her father signing off. The investigators concluded the difference was borne of disorganization rather than malfeasance. Both Regalados agreed to pay $5,000 fines.

"It did look like sloppiness," Joe Centorino, director of the county ethics commission, told the Miami Herald in 2012. "They were going through some personal issues."

 

Regalado, the school board's facilities chairperson, meets with staff at Citrus Grove.
Regalado, the school board's facilities chairperson, meets with staff at Citrus Grove.
Photo by Marta Xochilt Perez

Indeed, they were. In 2009, the year her mom died and she divorced her husband, Raquel officially learned what she had long suspected: Her daughter, Isabela, then 5 years old, was autistic. The diagnosis came in August, just days before Isabela was scheduled to begin kindergarten at Miami Children's Museum Charter School. Raquel says her daughter, now 11, is "mid-spectrum" -- she is highly intelligent and reads at grade level, but doesn't interact on a normal social level and struggles with verbal communication. "She has really taught me about patience and seeing things differently," the school board member says. "I've learned to see things from her perspective."

Raquel also has a son, Sebastian, two years younger than his sister. Regalado is on good terms with Herrera, but raising two children -- one with special needs -- has been extraordinarily difficult, she admits. Hardest of all is trying to prepare her daughter to one day survive without her. "I want her to be successful," Raquel says. "And I want her to have as normal a life as possible."

Just days after Isabela was diagnosed, the charter school told Raquel the facilities weren't properly equipped for a special-needs student like her daughter. They had to rescind her admission. In the coming months, Raquel visited more than 30 schools around the county. She inquired about autism programs, often receiving "weird reactions" from staff, none of whom had any idea that she was the parent of an autistic child. "They were kind of negative about it, like 'You don't have to worry about those kids here,'" she says, "which obviously was insulting."

One day in early 2010, Raquel sat with her dad at Maria's Greek Restaurant on Coral Way. She said she was frustrated in her search for a school. After about 15 minutes, Tomás said that if she really felt so strongly, she should run for school board. A light bulb went off. "I was like, 'You know what? That's a great idea!'" Raquel remembers. "'I think we'll run.'"

Seven months later, in the August election for School Board District 6, which includes Coral Gables, Coconut Grove, and Little Havana, Raquel won nearly 60 percent of the vote in a field of five. During the campaign, she never mentioned Isabela's autism. But she raised an astounding $172,000, more than twice as much as Eduardo Zayas-Bazán, a retired language professor and Bay of Pigs veteran who came in second.

She won union support and proved a hugely effective campaigner, talking easily about budget issues and connecting with voters. It was a strategy she says she'll re-employ in an upcoming political bid. "We're going to drill down to what the issues are," she says. "I think people respond to that, and it works for me."

In December 2011, with Isabela's special-needs status still unknown, Raquel received a phone call from Myriam Marquez, then the editorial page editor for the Miami Herald. The newspaper was doing a story about children with disabilities who were being excluded from public schools, but she was having trouble finding parents willing to go on the record. "Hey, Raquel," she remembers Marquez saying, "I know you do a lot of work with children with disabilities... Can you talk to these parents?"

"And I remember thinking, This is the moment," Regalado says. She told Marquez she'd get right back to her and then sat down and quickly wrote a letter. The next day, the Herald published an unusual op-ed. The headline was "Regalado: My Untold Story."

"Sometimes purpose trumps privacy," Regalado wrote. "Today I share with you that I am the mother of an autistic child and that I am an elected official, because after years of trying to change my daughter, she changed me."

From the outset of her tenure on the board, Regalado has been a change-maker. But in her first six months, she says, the brazenness mostly backfired. "They just voted against everything," she says. "Like, I could have come in with an agenda item that said the sky is blue, and they would have been like, no."

"She's challenged... the establishment... She's taken on issues in the community."

Since then, she has committed herself to collaborating and has emerged a remarkably popular, if at times controversial, leader. In addition to her work advocating for autistic students by spearheading magnet programs and securing "sensory rooms" -- special therapeutic spaces for autistic children -- she has also earned praise for high-profile initiatives such as directing the district to adopt the nation's first school district social media policy, which provides guidelines for teacher-student relationships on sites like Facebook and Twitter. In February 2012, after months of appealing to the board, Regalado's initiative to develop such a policy passed by an eight-to-one vote. "When I first brought it, it was very controversial," she says. "No school district had done a social media policy, anywhere... We did it."

Regalado has at times rankled her colleagues. One example is her advocacy for a new, high-performing high school in downtown Miami. "She's challenged... the establishment," says longtime school board lobbyist Jorge Lopez. "Her tougher issues have been outside the school board -- she's taken on issues in the community."


When it was completed in 1928, the 28-story Miami-Dade County Courthouse on Flagler Street was the tallest building in the Southeast. In 1930, Al Capone was famously acquitted for perjury inside the building, and for years its top floors doubled as a jail. In 1989, "Cielito Lindo," as the building became known, was added to the National Register of Historic Places.

But the city's most iconic downtown public building is in notoriously bad shape. The basement is horribly flooded, the roof leaks, several floors are moldy and cordoned off, and chunks of the building's façade have been known to fall off, posing a risk to pedestrians below. The problems have plagued the county for decades, but it wasn't until late last summer -- a few months before the November election -- that the building ignited a political firestorm.

 

Every weekday at 2 p.m., Regalado hosts a call-in radio show, Las Dos Caras de la Noticia, on the Spanish-language station La Poderosa.
Every weekday at 2 p.m., Regalado hosts a call-in radio show, Las Dos Caras de la Noticia, on the Spanish-language station La Poderosa.
Photo by Marta Xochilt Perez

On August 7, timing that some critics would later call suspicious, a city inspector posted a violation notice that the building lacked proper certification. The legal community, led by 11th Judicial Circuit Chief Judge Bertila Soto, rallied around a plan to build another courthouse with new property taxes. County Mayor Carlos Gimenez vocally supported the idea, arguing that seeking to repair the existing building was futile. "Let [the people] vote it up or down," the political blogger Elaine de Valle reported Gimenez saying in September, "because we need a new courthouse."

Soon a referendum was added to the November ballot to ask if voters would approve a $393 million bond for the project, and Raquel Regalado -- in perhaps the most important decision of her political life -- emerged as the face of the opposition. "Someone said, 'Oh, we're just going to do what they did [with the bond referendum] at the school board,'" Regalado says, characterizing the early effort by proponents. "Actually, no, we're not going to do that. That's a bad idea."

When Raquel was considering whether to voice her discontent, she conferred with her father, whom she talks to every day before 7 a.m. "She said to me: 'Hey, Dad, this is wrong... I think the judges are going about it the wrong way,'" the elder Regalado recalls. "I told her: 'Listen, Raquel, you have had a good four years on the school board; you have done everything right. Why do you want to piss off all the judges?'"

Raquel answered that she thought it was ill-conceived, that opposing the bond was the right thing to do. Tomás challenged her, he says, and warned that she would face an overwhelming amount of negative publicity. "But who are you?" he pressed. "What is your role in this?"

Raquel insisted, proving just as stubborn as she had been about eating red beans. "That is typical of her," Tomás says. "She will crash and burn if she thinks that is the right thing."

In the coming months, she didn't crash, but she certainly burned. In more than 50 radio and TV appearances, debates, and forums, she vehemently criticized the bond, decrying it as fiscally irresponsible and hastily planned. Just as her dad had predicted, she earned harsh criticism, mostly from bond proponents who saw her engagement as a not-so-concealed effort to score political points. "It was clear that the only point was to get as much airtime and publicity as possible for herself, regardless of the merits of the issue," says Ricardo Martinez-Cid, the president of the Cuban American Bar Association and a leading proponent of the bond.

Worse, Martinez-Cid says, was that Raquel didn't seem to care about getting her facts right or seeking a solution. In one radio debate, for example, Martinez-Cid says he corrected her on-air when she said a new courthouse was being built at the Caleb Center, when the site was actually a new parking lot. Martinez-Cid says he was later taken aback to hear her repeat the same argument a few days later on television. "She was about sound bites, and she was about media attention," he says. "She wasn't really about solutions."

(Regalado maintains she was right in her arguments about the Caleb Center with Martinez-Cid. "I'm not a demagogue," she wrote in an email. "I just pointed out the flaws in their 'plan' and asked for a better process.")

"If she's attacked, she gets stronger."

In another radio debate, she argued the county was to blame for the deteriorating state of the building. Lopez, the school board lobbyist, who was also a bond proponent, countered that the city shared responsibility. "¡Dale!" Regalado replied. Bring it on. "She kind of pulled a Pitbull," Lopez says. "I kind of looked at her like, 'Whoa.'"

Mikki Canton, a high-powered lobbyist and a longtime mentor to Regalado, says the battle over the courthouse brought out the fighter in Raquel. "If she's attacked, she gets stronger. And I think that has a lot do with the way she was raised."

On November 4, the bond measure failed by a margin of nearly two-to-one. Regalado claimed a victory for fiscal responsibility -- and seized on the opportunity to rip into Miami-Dade. "It's a clear mandate against burdening taxpayers for Miami-Dade County's mismanagement," she told the Herald. "It's an indictment of the county's lack of planning."

She said "county," but she may as well have named Mayor Carlos Gimenez, her possible future opponent for the most powerful government job in South Florida. A few months later, in mid-January, Regalado attacked again, blaming Gimenez for the county's slow disbursement of property tax money to the school board.

This time the county mayor returned fire. "I believe that this is political," Gimenez told the Herald's editorial board, "and has to do with someone's political aspirations."


At Bocadito Express, the café next to La Poderosa, Regalado slowly finishes her croquetas, talking only slightly less quickly than usual, and heads upstairs to the drab studio. She takes a seat near a collection of miniature Latin American flags and a small portrait of Christ, then positions her mouth a few inches from several microphones.

For the next hour, she banters in rapid-fire Spanish with the mayor of Sweetwater. Then she addresses del Valle, the Political Cortadito blogger, then various listeners. Sometimes she scrolls through her phone as the guests talk, or smiles in amusement, or shakes her head. But on the air, she's flawless. She always jumps in at just the right moment, the words pouring from her mouth as naturally as air. Her tone is challenging when she's making a point, then gentle when urging a caller to speak up.

After the show ends, Regalado quickly walks out of the studio, but she doesn't stop talking. She slips into stories of her family -- how her grandfather taught her Cuban geography, how her grandmother's sisters showed her how to knit. But the biggest influence, of course, has been another relative, the one who still has Raquel's ear every morning.

Tomás Regalado's final term as mayor of the City of Miami ends in 2017. Were Raquel to seek that office, she'd be a virtual shoo-in, with a built-in network of her father's supporters eager to see his legacy transferred to his telegenic daughter. The takeaway after recently talking to one lobbyist, she says, was, "You just breathe from now until 2017, and you would be elected at the City of Miami."

But the more powerful, county position, which comes up in November 2016, along with the presidential election, would be much tougher. Gimenez, although deeply unpopular in some circles, has already said he'll run again and still enjoys strong financial support. Raquel, without any managerial experience, would be the political newcomer. "Can she come up with a narrative that gets people away from challenging her ability on the administrative experience?" Lopez asks. "She's going to have to overcome that challenge."

Yet Regalado, as a woman and as a relatively young outsider, would also charge the race with star power. "She has a strong understanding of the issues," says County Commissioner Xavier Suarez, who has hinted he might also join the county race. "She would be a formidable candidate, and she would be qualified. I'm not saying she would be more qualified than me."

For his part, the mayor of Miami says he'd prefer to see Raquel in the more powerful, county spot. "Knowing Raquel, if she runs, she wins," Tomás Regalado says. "I can tell you that."

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