A dark money mystery in Florida

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.