Jesse Scheckner
A new Miami-Dade group supporting Republican influencer Alex Otaola’s bid for Mayor has enlisted the consulting services of convicted political operative Roger Stone.
Miami-Dade a Communist Free Zone, an electioneering communications organization (ECO) that registered with the county in March, paid more than $12,000 to Stone’s Drake Ventures last month.
The ECO’s Chair, Luis Leon, confirmed Otaola is the only candidate it’s currently backing.
“He is the only person whose campaign fits our agenda,” he told Florida Politics on Monday.
“As Mayor, he will dig in, investigate and stop all the businesses in South Florida and especially Miami-Dade that are supported or financed by communist regimes such as Cuba, Venezuela and Nicaragua. And he will prevent the communist agenda from getting into the education system and indoctrinating students in South Florida.”
There were questions Wednesday about the legitimacy of the payment to Stone’s firm. Drake Ventures is technically defunct. It’s not in good standing with either the Division of Corporations in Delaware, where it’s principally located, or in Florida, where its license is listed as “revoked” since September 2022 for failing to file an annual report.
As of 5 p.m. Thursday, the company was again listed as “active” and in good standing. Political strategist Grant Smith told Florida Politics the prior listing was an “administrative oversight” and that Drake Ventures was in good standing as of this week.
“This was nothing more than delayed paperwork and payment of the annual fee,” Smith said by email. “These are things that sometimes fall through the cracks.”
In July 2022, Stone and his wife, Nydia, who co-owns Drake Ventures, settled a $2 million lawsuit with the U.S. Department of Justice over several years of unpaid taxes, penalties and interest. The settlement came more than a year into legal proceedings in which the government accused the Stones of trying to “defraud the United States” by dodging their debt and about a month after Fort Lauderdale U.S. District Judge Rodolfo Ruiz II ordered them to hand over additional documents related to the case.
Both Otaola and Roger Stone are stalwart allies of former President Donald Trump, who pleaded not guilty Tuesday in a Miami courtroom to 37 felony counts of mishandling classified documents.
For years, Stone encouraged Trump, a longtime friend, to make a run at the White House and worked in both official and unofficial capacities for the former President’s 2016 campaign. In July 2020, Trump commuted Stone’s three-year prison sentence for obstruction and witness tampering during a congressional investigation into Russian election interference.
Asked during an online video broadcast in late February about whether he had “a horse in the race” in the Miami-Dade Mayor’s race, Stone named Otaola, a popular Cuban American social media influencer and political activist as his preferred candidate.
“He is a strong, America-first proponent, and many of his friends are urging him to run for Mayor of Miami-Dade County in 2024,” he said. “It is an intriguing idea. Like Donald Trump, Alex Otaola is not a politician, and he’s also a man who absolutely speaks his mind, and I think that that is what people are looking for.”
Otaola gained national attention in the lead-up to the 2020 election while promoting Trump on his Spanish-language YouTube channel, which now has more than 300,000 subscribers.
In late 2020, the Trump campaign was among Otaola’s paid advertisers.
Otaola is running to unseat Miami-Dade Commissioner Daniella Levine Cava, a Democratic former county Commissioner and nonprofit executive who holds more than $1.3 million to fund her re-election effort.
Otaola, who entered the 2024 race in April, has raised more than $52,000 through mostly small, individual donations. Miami-Dade a Communist Free Zone has raised $18,000.
A third candidate, Democratic trapeze artist and self-described First Amendment auditor Miguel “El Skipper” Quintero, has $1,000 so far, all of it his own money.
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Editor’s note: This report has been updated to reflect the current “active” status of Drake Ventures on the Florida Division of Corporations website.
