A month before Election Day in Florida a mysterious company called Proclivity, Inc. contributed $550,000 to a pair of newly formed political action committees in the state.
Two days later, the money flowed from the PACs to an Orlando-area print and advertising firm.
Shortly thereafter, came a torrent of nearly identical political fliers seemingly intended to siphon away support from Democratic candidates by tricking voters into casting their ballots for purported spoiler candidates who demonstrated no real interest in getting elected. None, for example, engaged in typical campaigning activities or raised significant funds.
In one case, the mailers appear to have helped a Republican—a co-founder of Latinas For Trump—unseat the Democratic incumbent in a state Senate race by a razor-thin margin of just 32 votes.
The situation, which has been generating headlines in Florida for weeks, has all the makings of a “dark money” mystery in the Sunshine State.
Among the key questions: What exactly is Proclivity and what was the purpose and desired effect behind its generous contributions to the two fledging PACs? And, why did those PACs support unknown candidates with no party affiliations and no real chance of winning?
CNN has learned that Proclivity was created in Delaware in 2019. Its president is listed in its corporate filings as Richard Alexander. Attempts to reach Alexander were unsuccessful; a phone number for the company is no longer working and its listed address is a UPS store in Atlanta. Staff at the store confirmed that Proclivity had a mailbox, but declined to provide any additional information, citing client confidentiality.
Though Proclivity’s money paid for advertising ostensibly targeting Democratic voters, it flowed through a pair of PACs, one of which has connections to a young Republican political strategist named Alex Alvarado. Alvarado’s stepfather is president of the company paid to print the fliers. The company is run out of an Orlando-area home that Alvarado’s stepfather and mother own, records show.
Alvarado, a former congressional intern and entrepreneur, declined to be interviewed for this story. Records show that his firm, Alvarado Strategies, was paid more than $267,000 so far this year for its political work.
The two Florida PACs that received the Proclivity contributions were both registered on the same date and time — October 2 at 11:34 am, according to Florida Division of Elections documents.
One day later, one of the PACs – Our Florida PC – got $370,000 from Proclivity; the other – The Truth PC – got $180,000.
The PACS are each chaired by women in their mid-20s who appear to be newcomers to the political scene. Neither woman responded to multiple messages left for them at the phone numbers listed for the PACs. Attempts to reach them through various other means were unsuccessful.
Sierra Olive, who is listed as chair of Our Florida PC, once shared an address with Emily Leiva, the woman with whom Alvarado currently owns a house, according to records. Olive posted a photo of herself and Leiva to Facebook in 2017 with the caption “favorite human.”
Leiva did not respond to multiple requests for comment.
Some of the fliers paid for by Our Florida PC and The Truth PC contained identical language referencing typically Democratic themes such as fixing health care, fighting climate change and speaking truth to power. They were circulated in at least three state Senate races in which a non-party affiliated candidate was running in addition to a Democrat and Republican.
In the South Florida race featuring the Latinas for Trump candidate, the purported spoiler candidate had the same last name – Rodriguez – as Democratic incumbent Jose Javier Rodriguez.
Though he has no known history in politics and did not actively campaign, Alex Rodriguez garnered more than 6,000 votes. When questioned by a Miami TV reporter after the election, Rodriguez lied about his own identity, according to WPLG, a CNN affiliate in South Florida.
Rodriguez was charged with two counts of felony grand theft in 2012, according to court records. He pleaded guilty, though adjudication of the charges was withheld, the documents show.
In another case, Miami attorney Juan A. Sanchez said Rodriguez went missing after paying only a portion of what a judge ordered him to pay to a client in a dispute involving a worthless check.
“We couldn’t track him down,” said Sanchez, who said Rodriguez was eventually found living in Boca Raton, Florida. “He gave a sob story that he was broke and had no money.”
The attorney said he struggles to believe that Rodriguez seriously sought to become a state senator.
“That would be something incredible,” he said.
Alex Rodriguez did not respond to CNN’s request for comment. His attorney, William Barzee, declined to comment.
Jose Javier Rodriguez, the incumbent state senator who lost by 32 votes, has called for a probe into Alex Rodriguez’s candidacy and who is behind it.
“Democracy requires transparency,” he said in a video shared with the media, “and in order to achieve that I believe this election warrants a full investigation.”
Ileana Garcia, the newly elected Republican state senator, side stepped questions from CNN about her involvement – if any – in the other Rodriguez’s campaign.
“I will not allow this temper tantrum to distract from the important work ahead,” Garcia said, in part, in a statement.
Erin Isaac, who serves as a spokesperson for both Garcia and Florida’s Republican Senatorial Campaign Committee, said the committee had no connection to Alex Rodriguez’s candidacy.
“Did we have anything to do with it? My answer is no,” she said.
The Miami Herald, citing “sources with knowledge,” reported last week that Miami-Dade prosecutors have launched an inquiry into Alex Rodriguez’s candidacy. A spokesperson for the office declined to confirm or deny the existence of an investigation to CNN.
Ben Wilcox, research director of the nonpartisan watchdog group Integrity Florida, said he has no doubt that someone running a dark money campaign impacted at least one state senate seat.
“Florida is so loosely regulated when it comes to financing of campaigns that it’s probably legal, but it really shouldn’t be,” Wilcox said. “It’s a disservice to voters and it calls into question the integrity of our elections.”
CNN’s Amitoj Singh, Yahya Abou-Ghazala, Cybele Mayes-Osterman and Benjamin Naughton contributed to this report.