Political dynasties battle behind the scenes in Miami special election

Miami Herald

22-05-2025

In the business world, it's not what you know, but who you know. The same can often be said for Miami politics.
But at a time of heightened criticism of so-called political dynasties, a candidate's proximity to power can be a double-edged sword.
That's the dynamic that's been playing out in the upcoming city of Miami election to replace District 4 Commissioner Manolo Reyes after his death last month.
On one side is Jose Regalado, 40, the brother of County Commissioner Raquel Regalado and son of former Miami mayor and current Miami-Dade Property Appraiser Tomás Regalado. He has the backing of the Reyes family.
On the other side is Ralph Rosado, 52, an urban planner whose candidacy is backed by Commissioner Joe Carollo's political committee, which has been funding anti-Regalado ads. Rosado is also friends with former City Attorney Victoria Méndez, a Carollo ally who was fired by the City Commission last year.
No matter who wins, the June 3 special election could tip the scales of power on the five-member City Commission, where important decisions are often made by a 3-2 vote.
Within a matter of days of being sworn in, the new commissioner is expected to weigh in on major decisions about the future of the city, potentially casting the tiebreaker vote on a proposal to create stricter term limits for elected officials. They could also be a deciding vote on a proposal to skip the upcoming November election and extend the current elected officials' terms by one year in order to switch the city to even-year elections starting in 2026.
The candidates' political alliances have been a focal point during the short special election cycle, where campaigning has moved at a breakneck speed, with just a little over a month from the candidate qualifying deadline to Election Day.
Regalado described his opponent as 'a serial candidate who's backed, funded and directed by Joe Carollo, the person at the center of the dysfunction in City Hall.'
'His campaign is built on misinformation and fear, all to ensure Joe Carollo keeps his grip of power,' Regalado added.
But to Rosado, the race is something closer to a David and Goliath battle.
'I'm running against a political machine,' Rosado said. The difference between himself and his opponent? 'Politics is not my family business.'
Rosado's ties to Carollo and former city attorney
Rosado has positioned himself as the non-establishment candidate, telling District 4 voters in a text message this month that: 'I'm not part of a political dynasty or backed by insiders. I'm a father of three, a longtime public servant, and your neighbor - running to bring fresh leadership to City Hall.'
But the former North Bay Village manager has the backing of Carollo, a Miami politician considered an establishment unto himself.
READ MORE: Miami's political godfather Joe Carollo, unfazed by $63M beating, can't wait for next fight
Carollo's political committee, Miami First, has paid for a flurry of anti-Regalado mailers and ads on Telemundo and Univision. Carollo, who is chairman of the political committee, declined to say how much money Miami First has spent on the District 4 special election but said it hadn't yet reached six figures. Campaign finance reports, which are released on a quarterly basis, aren't due until after the election.
Earlier this month, the blog Political Cortadito posted a video of Carollo seemingly directing a campaign video for Rosado at a park. Rosado told the Miami Herald he was filming a commercial 'paid for by me' and that Carollo happened to be in the area and offered to stop by.
'He had reached out and had some suggestions,' Rosado said. 'We listened to his suggestions. Some we took, some we didn't take.'
Rosado added that he would entertain recommendations from any member on the City Commission, where he hopes to be a 'swing vote.'
'I'm looking to be a moderate voice on the commission,' Rosado said. 'I'm not high drama. I think there's plenty of that. I just want to get things done for the community. So I'm happy to interact positively with any of the elected leaders.'
While Carollo is supporting Rosado's candidacy, he is not working for Rosado's campaign, which is being run by Jesse Manzano-Plaza, a campaign consultant whose clients include Miami Mayor Francis Suarez.
Carollo said his support for Rosado is not based on a personal relationship with Rosado, who previously ran for the District 4 seat in 2017, losing to Reyes.
'I don't know Rosado,' Carollo said. 'He's someone that I recently met. I think he's an honest man.'
Carollo added that Rosado is 'superbly qualified for this job,' touting Rosado's master's in public policy and urban planning from Princeton University and a Ph.D. in city planning from the University of Pennsylvania.
Asked if he considers Rosado to be an establishment-backed candidate, Carollo responded: 'Heck no.'
'Mr. Rosado is going to be a super independent commissioner,' Carollo said.
Rosado is also close friends with former City Attorney Victoria Méndez through his wife, who went to high school with Méndez. Along with Méndez's husband, the two couples have traveled together internationally, and Rosado and his wife previously rented a home from Méndez and her husband around 2013.
Rosado is the founding president of the nonprofit Abuelos Foundation, which helps distribute meals to seniors. He served alongside Méndez and her husband, Carlos Morales, on the board of the foundation for years, public records show. While Méndez and Morales are still board members, Rosado left the board in 2021, according to state business records, although he still volunteers with the organization.
Rosado emphasized that Méndez, who was city attorney for about a decade, is no longer in City Hall.
'She's the former city attorney,' he said. 'So that's — I don't know that I could consider her a part of the establishment.'
After being fired by the City Commission last year, Méndez was named partner at the law firm Shutts & Bowen. The city has retained Shutts & Bowen for various legal matters in recent years. The firm has invoiced the city for millions of dollars in legal fees relating to the Miami Freedom Park stadium project and a lawsuit filed by a pair of Little Havana businessmen against Carollo, according to public records.
If he's elected, Rosado said he would not seek to bring Méndez back to the city in any capacity, as city attorney or otherwise. 'I can't imagine she would want to come back as city attorney,' he added.
Rosado also said he would recuse himself from votes related to Méndez. Asked if he plans to recuse himself from votes on Shutts & Bowen, Rosado said he would seek a formal opinion from the City Attorney's Office and decide on a case-by-case basis. Méndez did not respond to an interview request or written questions from the Herald.
Rosado underscored that he would be an independent voice on the City Commission.
'I'm going to vote for the things that I think are right,' he said, 'and sometimes they will be supported by certain people, and other times will be supported by other people.'
Regalado courted by Reyes family
Up until last month, Jose Regalado was working in the city as an assistant building director and interim building director. He also spent two years as a policy adviser in Reyes' office from 2017, when Reyes was first elected, to 2019. Previously, he worked as an underwater photographer.
Despite growing up with a politician father, he has never sought elected office before.
That changed on April 19 when Jose Regalado got a phone call from Chacha Reyes, the widow of Manolo Reyes.
She had a request for Regalado: Will you carry on my husband's legacy and run for District 4 commissioner?
With less than a week to go before the deadline to file for the race, Regalado didn't have much time to think about it.
'I am a civil servant,' said Regalado. 'And then a widow asked me to do this, and I couldn't say no.'
The next day, Easter Sunday, Regalado met with Chacha Reyes at her home, and the day after, he resigned from his post in the city and announced his plans to run.
Since then, Regalado has had the full backing of the Reyes family, including Chacha, who recorded a commercial supporting him that's aired on Spanish radio.
The late commissioner's son, Manny Reyes, said his father did not support Rosado, whom Manny described as an 'opportunist.'
Instead, he said his dad was 'very, very close' with Jose Regalado.
'[Regalado] lived the district through his dad's eyes, knowing what his district was composed of,' Manny Reyes said. 'Much like myself, he was his dad's shadow.'
Jose Regalado's family isn't just cheering him on from the sidelines. Raquel and Tomás Regalado are both door-knocking for him, and Raquel is acting as his campaign manager.
'I have run every Regalado campaign since 1995,' Raquel said. Her father was elected to the Miami City Commission in 1996.
'All Regalados work on campaigns,' she said, adding that she's not being paid for her work on her brother's campaign.
Tomás Regalado's political committee, Proven Leadership for Miami, has been fundraising for Jose, who said it was more efficient to use the preexisting political committee rather than start from scratch in the shortened special election cycle. (While similarly named, that political committee is separate from the one linked to former City Commissioner Alex Díaz de la Portilla, called Proven Leadership for Miami-Dade County.)
The political committee linked to Reyes, Transparency & Accountability for Miami, is also spending money in the race.
Outside of work hours, the majority of Reyes' District 4 staff is campaigning for Jose Regalado, who has committed to retain them if he wins. Two District 4 employees have taken unpaid leaves of absence from the city to commit to campaigning full-time through the election. City staff are allowed to campaign as long as it happens outside of work hours and doesn't interfere with city work.
Carollo in recent weeks has taken aim at the Regalado family, with his political committee funding a flurry of attack mailers and television ads. Carollo has argued that Jose Regalado is unqualified, pointing to his recent job in the city's building department, as well as his experience as an underwater photographer.
'Maybe he found the lost city of Atlantis and he did some building there that we don't know about,' Carollo told the Herald.
The pair are likely to spar on the dais should Regalado be elected.
'Joe is an agent of chaos,' Jose Regalado said. 'Something that I have in common with both Manolo and my dad is that I'm not scared of him.'
Third candidate dropped out after property appraiser investigation
In the days immediately following Reyes' April 10 death, a third candidate was considered to be the heir apparent for the role: Rafael 'Ralph' Cabrera, president-elect of the Latin Builders Association, who also had the support of the Reyes family at the time.
But Cabrera's candidacy was thwarted after an investigation by the Miami-Dade County Property Appraiser's Office — which is headed by Tomás Regalado — dredged up residency issues for the would-be candidate.
Records obtained by the Herald show that on April 14, an unnamed individual contacted the Property Appraiser's Office, alleging Cabrera 'does not reside' at his homesteaded property, located in District 4, and to 'please investigate.'
The homestead fraud investigation concluded that same week. On April 18 — the day after the City Commission called for a special election to replace Reyes — a letter from the Property Appraiser's Office to Cabrera stated that he was not entitled to the homestead exemption he had claimed for years on that property and that he owed nearly $40,000 in fines. Those findings seemingly disqualified him from running for Reyes' seat. Cabrera did not respond to a request for comment.
Rosado has alleged that politics were at play, suggesting that Tomás Regalado was motivated to get Cabrera out of the race so that his son could run instead. 'He did this in record time,' Rosado said. He added that he didn't file the initial complaint, nor did he know who did.
Tomás Regalado told the Herald he had no involvement in the investigation, nor was he aware of it while it was happening. He said his office receives hundreds of complaints per month and that it's 'the norm' for such investigations to conclude in a matter of days.
The elder Regalado said that his office is required to look into every complaint, even if it's anonymous.
'To me, it was a surprise,' Tomás Regalado said. 'At the time, Jose was not even thinking of running for this position.'
Manny Reyes confirmed that his family initially supported Cabrera. In fact, Cabrera attended the April 17 meeting where the City Commission decided to call for a special election.
'We were ready to support Ralph [Cabrera],' Manny Reyes said. But the residency issue created a roadblock.
At that point, it was time to pivot. Enter Jose Regalado.
'It's a sprint,' Manny Reyes said of the brief special election cycle. 'Think fast, act fast.'