Rosario Kennedy and Monty Trainer are lobbying for Del Mastro Outdoor billboard company
A New York-based billboard company is relying on a pair of grizzled Miami City Hall insiders to push through a pilot program that would allow advertisements on construction site fences in the city’s urban core.
Longtime Coconut Grove entrepreneur Monty Trainer and ex-Miami City Commissioner Rosario Kennedy are the lobbyists for Del Mastro Outdoor, which would have the exclusive rights to place static billboards in lieu of regular construction fencing at sites with active building permits under a resolution that is back on the city commission agenda for Sept. 10.
The legislation, sponsored by Miami’s District 1 City Commissioner Miguel Gabela, was deferred in June following backlash from downtown Miami residents.
James Torres, president of the Downtown Neighborhood Alliance, said residents in the urban core are fed up with the proliferation of advertising signage. “We are up to our neck with billboards,” he said. “It is more visual pollution.”
At the Sept. 10 meeting, city commissioners will also consider an ordinance to allow temporary banners in downtown Miami to promote the release of Grand Theft Auto 6: Vice City, the highly anticipated video game which is based on the Magic City.
The idea that replacing a construction fence with a billboard will deter graffiti artists is ludicrous, according to the nonprofit Scenic America. “Billboards do not improve community character or reduce visual clutter,” the group said in a statement on the Scenic America website. “They add to it.”
Scenic America also noted the sole source exclusivity being provided to Del Mastro, a firm led by Dawn Del Mastro-Chruma:
“The proposal also raises significant public-policy concerns by designating a single private advertising company as the exclusive participant in the pilot program, without a competitive bidding or open qualification process.”
Del Mastro-Chumra is not super active in political campaign donations, but she did donate $1,000 on March 27 to New Leadership for Miami, Rosado’s political action committee. Instead, Del Mastro is relying on the staying power of Trainer and Kennedy.
One of Del Mastro’s construction site billboards
Kennedy, an 81-year-old Coconut Grove-based lobbyist, was the first Cuban American and Hispanic woman elected to the city commission when she beat Demetrio Perez in 1985. She left office four years later, and has run a successful lobbying practice since then.
Del Mastro has apparently been laying the ground work for construction fence advertisements for the past two years. According to city lobbying registration reports, Del Mastro hired Kennedy in 2024 to assist its efforts “to beautify certain sites and enhance the safety and visual environment of the city.”
Trainer, 89, came on board in June to assist Del Mastro in a “Graffiti Abatement Program,” according to his lobbyist registration. The billboard company is Trainer’s only client.
Trainer, who served 133 days in 1989 and 1990 in a minimum-security prison after pleading guilty to a federal charge of making a false statement on his income tax return, is the brains behind Monty’s, the landmark waterfront restaurant in Coconut Grove where he brokered agreements and cut deals involving city policy.
Last year, the city commission voted to rename a section of Aviation Avenue in Coconut Grove to Monty Trainer Way.
Under Gabela’s proposed resolution, Del Mastro would pay the city 15 percent of gross advertising revenue from participating construction sites, as well as a $10,000 pre-qualification fee and a $500 permit fee for each billboard, which would have a maximum height of eight feet.
The payments to the city would “be used to ensure and improve the quality of life throughout the City of Miami,” the resolution states.
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