Last week, the anonymous gumshoe posted photos, videos, and other De la Rosa-related documentation of the stakeout in a Google Drive folder. New Times first received a link to the Google Drive from a well-connected tipster who got it from a burner account on social media. Days later, a second tipster passed along the identical links.
The Google user, under the name "Justice Hialeah," claimed the surveillance showed that De la Rosa lives at a residence in Coral Gables and not at his registered address, the Hialeah home of the 28-year-old councilman's mother and stepfather, Miami-Dade County Commissioner Esteban "Steve" Bovo, who is running for county mayor in the November 3 election.
"Oscar does not actually live at that stated address, neither at the time of running and being elected nor now as a sitting council member," states a document in the Google Drive folder.
The timing of the information dump appears not to be a coincidence. The abovementioned document makes numerous references to Bovo and asserts that the mayoral candidate "is implicated in this."
"Since the address Oscar used in order to run was Bovo's own home, Bovo was aware that Oscar was committing a crime, and if anything aided him in this effort," the document states.
A relative newcomer to politics, De la Rosa was elected to the Hialeah City Council last November and won't be up for re-election until 2023. When contacted by New Times, he said he suspects the surveillance operation has more to do with his stepfather's ongoing mayoral campaign. Bovo, a longtime politician, is up against fellow county commissioner Daniella Levine Cava in the November 3 election.
Among the Google Drive files are two logs that purport to show GPS monitoring of De la Rosa's car. According to the logs, the councilman spent two consecutive nights at the house in Coral Gables in late September. (New Times was unable to independently confirm that the GPS logs are authentic.)
A video camera that appears to have been mounted across the street from the Coral Gables home captured De la Rosa's Range Rover coming and going from the property as early as 5:20 a.m. and as late as 10:21 p.m. over a period of several days. Paparazzi-style photos depict De la Rosa in the front yard with a young woman, his car parked on a grassy swale just off the street.
The Google Drive folder also includes a two-minute video that appears to have been shot with a body camera. The person wearing the camera delivered flowers to the Coral Gables house on the afternoon of October 9, according to the timestamp.
De la Rosa seemed confused when he opened the door.
"Did you not order it?" the deliveryman asked.
"No, I didn't," De la Rosa responded.
When the deliveryman asked whether someone else at the address might have ordered the flowers, De la Rosa replied, "I mean, it's not my house."
Reached by New Times, De la Rosa says the Coral Gables home is his girlfriend's residence and that he sometimes stays there overnight.
"It's her name on the lease," he says. "I hang out at my girlfriend's house."
De la Rosa says he lives at the Hialeah home with his mother and Bovo.
"We live together," he says. "I've lived in Hialeah over 20-something years."
caught then-presidential candidate Gary Hart at his D.C. townhouse with a woman who was not his wife — the industry's financial straits have left scant resources for that kind of shoe-leather expenditure.
That makes the De la Rosa stakeout all the more bizarre. New Times was unable to determine who performed or ordered the surveillance, but timestamps show that it was conducted over a period of at least 11 days, which suggests a significant investment of time and money.
And to what end?
In Florida, a lawmaker can be arrested for falsely claiming they live in their district, but the bar for an arrest is high.
If De la Rosa has simply been sleeping at his girlfriend's place, as he says, it's unlikely that he violated Florida law, says Peter Cruise, director of Florida Atlantic University's LeRoy Collins Public Ethics Academy.
"I think where one sleeps at night is totally up to you and wherever you’re gonna sleep, but it has nothing to do with residency in this state," Cruise tells New Times.
De la Rosa, for his part, says he's done nothing wrong.
"This is 115 percent a complete political smear job," he says.
Bovo, a Trump supporter who is running on a conservative platform, did not respond to phone messages or emails to his county commission office and his campaign headquarters.
A campaign spokesperson for Levine Cava, a progressive liberal, tells New Times her campaign had nothing to do with the surveillance materials and learned about them only after being contacted by New Times.
Miami-Dade Democratic Party chair Steve Simeonidis also denies that the party had anything to do with the surveillance detail.
"It definitely didn't come from us. This is the first I'm hearing of a Google Drive or anything like that," he tells New Times.
Hialeah's city code states that anyone who is a city resident and meets other Florida qualifications may run for office. The state requires that a candidate be at least 18 years old, a U.S. citizen, and a permanent resident of Florida.
The question of where an elected official lives, while seemingly straightforward, can turn out to be a complicated legal calculation. In Florida, residency is typically defined as a home where a candidate "intends" to have a permanent place of living. (The Orlando Sentinel recently published an in-depth report about how difficult it can be to determine a politician's actual place of residency.)
But elected officials can and have been arrested for lying about their official residence. To build a case, prosecutors often spend months interviewing landlords and neighbors or tracking down homestead-exemption filings and other documentation. Most recently, Sweetwater Commissioner Sophia Lacayo resigned in late August after pleading guilty to a perjury charge related to her residency. The landlord of the property told prosecutors she did not live at the home.
In Florida, there are no clear-cut guidelines about how many nights an elected official must stay at their declared residence, says Cruise, the FAU ethics expert. Typically, the issue of residency must be sorted out in court if a complaint is lodged against a politician.
Cruise says those hearings boil down to one question: "What does 'live' mean?" Courts generally give elected officials the benefit of the doubt about the place they call home, he says.
"Do you physically have to be there 24/7? No. Do you have to be there 51 percent of your time? That legal standard has yet to be determined by the [Florida] Legislature," Cruise tells New Times.
It's unclear whether the residency allegation against De la Rosa is being investigated in any official capacity. Spokespersons for both the Miami-Dade State Attorney's Office and the Miami-Dade Ethics Commission told New Times they could not confirm or deny the existence of an investigation.
De la Rosa provided New Times with copies of his driver's license, voter-registration card, and American Express bills, all of which list his address as the Hialeah home he says he shares with his mother and stepfather. In Florida, those documents can be used to bolster a lawmaker's residency claim.
A New Times reporter visited the property in Coral Gables on Tuesday morning, but no one answered the door. A porch light was on, but no cars were parked in either the front or back driveway. Neighbors said they did not know De la Rosa.
The owner of the Coral Gables property, Vivian De Val, tells New Times that while she does not know De la Rosa, she did rent the home to a woman who has the same name as De la Rosa's girlfriend.
New Times was unable to reach De la Rosa's girlfriend but did contact her mother, who confirmed in an email that her daughter lives at the Coral Gables property.
After learning he'd been surveilled, De la Rosa says he felt harassed. He insists that his living situation is aboveboard.
"I am duly elected and meet all legal residency requirements as a City of Hialeah Councilman," he wrote in an email to New Times.
Staff writer Joshua Ceballos contributed reporting for this story.