Cash deal with a mystery man in a parking lot led to a political crime, lawsuit says

The deal went down in a Flanigan’s parking lot on a hot, windy afternoon in late September. According to court documents, cash changed hands. And instructions were given to create an attack ad that may have violated several Florida laws.

So began another round of dirty politics in North Miami Beach.

On Sept. 27, a bearded, heavyset man in business attire and glasses who introduced himself only as “John” met Hector Roos, a local political consultant, in a Flanigan’s parking lot in downtown Fort Lauderdale, according to court documents. The records were from a lawsuit filed against Roos and include a narrative timeline of the day’s events, allegedly written by Roos himself.

When they met that afternoon, John instructed Roos to create and distribute a political attack ad that accused then-mayoral candidate Anthony DeFillipo of being a Tony Soprano-like mob boss presiding over a slate of criminals running for North Miami Beach City Council, according to court documents.

He paid Roos $4,750 in cash on the spot and promised more when the project was complete, according to Roos’ timeline. Roos was to carry out the job without further instructions or contact.

On Oct. 13, a two-sided mailer, riddled with spelling mistakes, was sent to North Miami Beach residents. “Tony ‘Soprano’ Defilippo’s Crime Family is asking for your support,” it said, spelling the mayoral candidate’s name wrong and accusing him and others mentioned of criminal behavior.


North Miami Beach Mayor Anthony DeFillipo

The small print on the mailer attributed the attack to AFSCME People, the political action committee of the largest union of government employees in the country. AFSCME denied involvement with the ad and is suing Roos for illegally impersonating the union and “acting to intimidate public officials in the name of a labor organization.“

DeFillipo is also suing Roos and others allegedly involved in the production of the mailer for defamation. The complaint called the mailer’s comparisons of the Italian-American politician to a mobster involved in criminal activity a hate crime.

After learning about the Flanigan’s parking lot deal, DeFillipo’s attorney, Michael Pizzi, also sent a letter to the Miami-Dade state attorney’s office on Dec. 20, asking that investigators look into possible money laundering, hate crimes, violation of campaign finance laws, and fraud associated with the solicitation and production of the mailer.

“This is one of the most blatant examples I have seen of powerful people completely ignoring campaign laws and basic decency in order to gain control of the local economy,” wrote Pizzi, while claiming local developers and special interests were likely behind the mailer.

John never contacted Roos again, according to the timeline submitted to the court. He was never paid additional money. And after spending $2,500 for printing and $2,181.37 for mailing, Roos was left with just $68.63 cents for his trouble.

Roos declined comment other than to say he does not expect AFSCME to continue with its suit due to lack of proof.