A $50 Million Mystery

By the time Rubio and Rivera sold their Tallahassee home in 2015 after facing foreclosure over disputed bank payments, Rivera had become a political liability.

During their four terms together in the Florida state legislature, Rubio harnessed the flair and showmanship of political theater. Rivera was the workhorse.

A power broker with meticulous attention to detail, Rivera wielded political muscle behind the scenes to pass landmark legislation on projects ranging from the buildout of the Port of Miami tunnel to a free-trade agreement with Colombia. An inveterate policy wonk, Rivera would fondly cite arcane provisions from these measures years later.

But alongside those accomplishments came accusations of graft. In Tallahassee, Rivera garnered a reputation as a “Nixonian” political operator for the lengths he would go to win. He once rear-ended a truck carrying incriminating campaign leaflets from his political opponent, according to a 2002 police report.

By the time Rivera lost his reelection for US Congress in 2013 after serving one term, he had been plagued by so many scandals that colleagues described his behavior as “pathological.” And some of his schemes reportedly implicated Rubio.

In the 2000s, the FBI investigated Rivera for a variety of transgressions, although it never brought charges. Among other matters, agents examined whether the legislator accepted bribes from gambling industry executives seeking to block Native American tribes from expanding their casino operations.

In a separate incident, both Rivera and Rubio faced scrutiny for voting to exonerate a fraudulent investment company that wagered on life insurance policies held by elderly and infirm AIDS patients after the two lawmakers received thousands of dollars in donations from a political action committee cofounded by the head of the operation.

Soon after, federal authorities investigated the company for allegedly laundering drug cartel money, eventually shutting it down and sending its top executive to prison.

In 2017, the Federal Election Commission filed a lawsuit against Rivera, alleging that he financed a straw candidate to run against his Democratic opponent in the 2012 primary for Florida’s Twenty-Fifth District in an unsuccessful effort to damage his electoral prospects. After pursuing the matter for years, regulators dropped the case at the start of 2025.

The State Department did not respond to a request for comment regarding Rubio and Rivera’s long-standing friendship and other matters. But for years, despite the slew of controversies, Rubio publicly defended his old roommate as he rose through the Republican ranks.

In 2022, however, Rivera faced charges that were far more difficult to overlook.

That year, federal prosecutors arrested Rivera and charged him — along with a fellow political consultant, Esther Nuhfer — with working for Venezuela in violation of the Foreign Agents Registration Act (FARA), which requires individuals and organizations to register with the Department of Justice when engaging in US political activity on behalf of foreign governments.

Enacted in 1938 in response to rising Nazi propaganda in the United States, the Foreign Agents Registration Act requires more stringent disclosures than ordinary lobbying, since foreign clients may have national interests that conflict with those of the United States.

“The question under the law is whether the benefit [of the lobbying] is purely private, divorced from a benefit or control by a foreign government or party,” said Joshua Rosenstein, a lawyer at the Washington firm Sandler Reiff, which advises clients on compliance with lobbying and ethics laws. “The greater the involvement of a foreign government or political party, the less likely it is that you can shoehorn your activities under an exemption.”

The statute also applies to “a person whose activities are directly or indirectly supervised, directed, controlled, financed, or subsidized” by a foreign principal.

According to the Justice Department’s indictment of Rivera, the problems originated in 2017, when he began lobbying on behalf of Citgo, the US subsidiary of Venezuela’s state-owned oil company.

For his work, Citgo paid Rivera’s consulting firm $50 million, a massive sum of money for a single lobbying firm. For comparison, the entire US oil and gas industry spent just over $120 million on federal lobbying in 2022.

Federal prosecutors allege that Rivera’s lobbying contract was actually a front for a foreign-influence campaign designed to avoid registering under the Foreign Agents Registration Act to conceal the full scope of the operation.

According to the indictment, Rivera was operating as an unregistered foreign agent to normalize relations between Venezuela and the United States — two countries that have been adversaries since socialist leader Hugo Chávez came to power in 1999.

Rivera was allegedly working for representatives of the Maduro government, which took power after Chávez’s death in 2013. Among the officials involved, prosecutors say, was then–vice president Delcy Rodríguez, who now serves as Venezuela’s president.

“It was the purpose of the conspiracy for the defendants to unlawfully enrich themselves . . . in an effort to influence United States foreign policy towards Venezuela and to conceal these efforts by failing to register under FARA as agents of the Government of Venezuela,” the indictment reads.

Rivera allegedly used his political connections as a longtime Republican lawmaker to arrange meetings between Venezuelan power brokers and US officials.

According to prosecutors, those meetings included a sit-down with Rubio as well as a meeting in Caracas between Maduro and Rep. Pete Sessions (R-TX), who represents the oil-rich Lone Star State, which has financial interests in Venezuela’s mammoth oil reserves. At the time, Sessions chaired the House Rules Committee, which plays a pivotal role in deciding what legislation receives votes on the House floor.

Kellyanne Conway, a senior counselor to Trump during his first term, also participated in several of the meetings, according to text messages included in the indictment.

Sessions and Conway could not be reached for comment.

In text message exchanges cited by prosecutors, Rivera and his associates used pseudonyms to obscure the specifics of these meetings. The Texas congressman was referred to as “Sombrero,” while millions of dollars were called “melones.” Their code name for Maduro was “El Guaguero,” a reference to the president’s early career as a bus driver.

These 2017 and 2018 meetings — some reported at the time — came at a fraught moment in US-Venezuela relations. Inside the Trump administration, officials were split over Venezuela policy, including proposals to tighten sanctions or normalize US business ties.

Officials ultimately chose the former, ramping up sanctions in 2017 and again in 2020.

At the end of 2025, Rivera’s defense team subpoenaed Rubio to testify about those meetings. Federal prosecutors subsequently decided to call Rubio themselves, apparently concluding that his testimony would strengthen the government’s case.

Rivera, whose lawyers refused to make him available for an interview with the Lever, denies any wrongdoing. His attorneys have argued in court filings that Rivera, a longtime critic of Venezuela’s socialist government, was working to undermine Maduro, not help him.

“We confidently believe that the evidence proves the opposite of what the government has alleged,” Rivera’s lawyers wrote in a December letter to the State Department requesting Rubio’s testimony.

“Specifically, then Senator Rubio and Mr. Rivera were focused only on their support for the Opposition [political leaders] in Venezuela, on sanctions against the Maduro government, and on removing Maduro as head of state in Venezuela.”

The Tycoon, the Trafficker, and the Trump Whisperer

As part of their defense, Rivera’s attorneys appear ready to suggest that the foreign-agent violations leveled against their client could just as easily be applied to another political operative: Wiles, Trump’s chief of staff.

To make their case, Rivera’s lawyers are zeroing in on two businessmen named in the indictment: a wealthy Venezuelan media mogul named Raúl Gorrín and a convicted cocaine trafficker named Hugo Perera.

Court documents claim that Gorrín, the politically connected head of a Caracas-based media company called Globovisión, helped orchestrate the alleged foreign-agent operation and served as a go-between for Rivera and the upper echelons of the Venezuelan government.

According to Rivera’s indictment, Gorrín took part in several of the meetings brokered by Rivera, including a sit-down with Rubio. Rivera also reportedly tried to use Gorrín’s private jet for the rendezvous with Conway.

Gorrín, who was sanctioned by the US government in 2019 for his purported involvement in foreign bribes and money laundering, was reportedly paid handsomely for his work.

In 2020, Citgo filed a lawsuit against Rivera for breach of contract. According to the suit, Rivera paid $4 million of his $50 million contract fee to Gorrín as a kickback for helping him land the arrangement. Rivera apparently funneled the money through Gorrín’s Miami-based yacht company.

The Lever did not receive a response from Globovisión for a request for comment from Gorrín.

The Citgo lawsuit also alleges Rivera paid $5 million to another subcontractor for help arranging the Citgo contract: Perera, a Miami real estate developer who was convicted in the 1990s for his role in a drug-smuggling operation run by the Cali Cartel in Colombia.

Perera’s name is notably absent in the government’s indictment, and he’s agreed to act as a cooperating witness against Rivera at trial. In retaliation, Rivera has countersued Perera for allegedly violating their confidentiality agreement. Rivera has also claimed in a court deposition that the FBI told him that Perera was an informant.

Perera, who now runs a Miami real estate company, did not respond to a request for comment.

At the same time that Gorrín and Perera were working with Rivera, court documents indicate that both men were engaged in related activities for Ballard Partners, a powerful US lobbying firm that Wiles coled at the time.

In 2017, the first year of the alleged foreign-agent scheme involving Rivera, Ballard Partners also registered to lobby on behalf of Gorrín’s Globovisión, seeking to expand the network’s presence on US television platforms. Ballard earned $450,000 from the contract, making Globovisión the firm’s third-largest client that year.

Ballard’s work for Gorrín appears to have been extensive. In a subpoena letter sent to the White House requesting Wiles to testify in the upcoming trial, Rivera’s defense team describes roughly four hundred pages of documents related to Wiles’s lobbying work gathered during the discovery phase of the case.

Court filings also reference numerous emails exchanged between Gorrín, Wiles, and other Ballard lobbyists. One of those lobbyists was Otto Reich, a former US ambassador to Venezuela who previously ran the interagency office that helped coordinate the Iran-Contra weapons sales during the Ronald Reagan administration.

Other Ballard emails went to Harry Sargeant, an oil executive who is currently advising Trump on his post-regime-change efforts in Venezuela. (Trump’s attorney general, Pam Bondi, began working at Ballard Partners in 2019 after serving as Florida’s attorney general, though she is not referenced in the correspondence described in the filings.)

Based on these email exchanges, Rivera’s lawyers also claim Perera was simultaneously working for Ballard while also serving as a subcontractor for Rivera.

“Discovery documents show that Hugo Perera, an important government witness in the case, was involved in these pro-Venezuelan activities through Ballard Partners at the same time the government has alleged that Mr. Rivera and Ms. Nuhfer were supporting pro-Maduro efforts on behalf of Venezuela,” the attorneys wrote.

“I Happen to Know That My Government Wants a Way Out”

Rivera’s lawyers do not accuse Wiles or her Ballard colleagues of illegal conduct. But their filings suggest the government’s legal standard for charging Rivera could potentially implicate a far wider circle of MAGA operatives — including the president’s chief of staff.

No federal records show that Wiles or Ballard Partners ever registered under the Foreign Agents Registration Act for any Venezuelan entity.

“We’re not taking a position on that [legal question] in the case,” said Ed Shohat, one of the defense attorneys representing Rivera.

Ballard Partners did not respond to multiple requests for comment. But the firm has publicly maintained that it complied with all foreign and domestic lobbying laws and that its work related only to Globovisión’s commercial interests in the United States. The lobbying firm dropped Gorrín as a client in 2018, amid a federal investigation that would lead to US sanctions against him the following year.

“Ballard Partners’ work for Globovisión involved Globovisión’s efforts to expand its TV network into the U.S. market,” Brian Ballard, the founder of Ballard Partners, said in a statement to the Miami Herald.

But a key document in the Rivera case obtained by the Miami Herald appears to suggest that Ballard’s work for Gorrín may have gone beyond strictly commercial interests.

In 2017, Ballard reportedly drafted a memo for Gorrín to provide to Trump, though he ultimately never delivered it. The letter apparently outlined a proposal to mend strained US-Venezuela relations by offering Maduro a path out of the country in exchange for a transition in leadership. As described by the Miami Herald, the document did not directly relate to, or mention, Globovisión’s access to US markets or other commercial interests.

“I happen to know that my government wants a way out, a way to save their skins and fortunes,” the draft letter from Gorrín read. “The opposition, on the other hand, wants a way in but is not unified in how to achieve its goals.”

Should Ballard Partners’ work on the Gorrín letter — or its other lobbying efforts — have required the firm to register under the Foreign Agents Registration Act? That’s likely impossible to determine without additional information about Globovisión’s relationship with the Venezuelan government.

“An exemption [to FARA] would be available, provided the client (Globo) isn’t directed/controlled by a foreign government or political party, and the principal beneficiary of the work wasn’t a government or political party,” said Rosenstein, the lobbying lawyer. “That’s a factual question.”

According to Rosenstein, foreign lobbying involves many legal gray areas, in part because the Justice Department has prosecuted relatively few cases, leaving the law with limited judicial precedent. Under Attorney General Pam Bondi, the Trump Justice Department has curtailed enforcement of foreign corruption and lobbying laws.

The hundreds of pages of Ballard records described by Rivera’s attorneys could shed light on the matter, but the documents may never become public. Last month, a federal magistrate judge in Florida’s Southern District Court granted a Justice Department petition allowing Wiles to avoid testifying at Rivera’s trial, thereby permitting related documents to remain under seal.

But in his ruling, the judge made a surprising admission.

“To be clear, no one disputes that Ballard Partners registered under FARA and dealt with Gorrín openly,” wrote Magistrate Judge Edwin Torres.

Torres’s office refused to comment. But if Torres is correct, it would mean that — despite no publicly available record of the filing — Trump’s chief of staff previously worked as a registered foreign agent for a government the United States recently moved to overthrow.

Under Pressure

Miami insiders say Rivera’s aggressive defense strategy isn’t just legal maneuvering ahead of trial; it’s also a political effort to pressure the Trump administration to drop the case.

That campaign includes issuing subpoenas to a striking list of high-profile witnesses, including not just Rubio but also Conway and Sessions. Rivera’s attorneys even subpoenaed Maduro, Venezuela’s deposed president, who is currently awaiting his own trial on US narco-terrorism charges. Maduro’s attorneys resisted the subpoena, saying their client would plead the Fifth.

While Miami defense lawyer Joseph DeMaria believes some of these witnesses could provide crucial testimony for Rivera’s defense, he also notes the political optics of such subpoenas.

“A lot of this strategy is political — to try to put pressure on the Trump administration to leave Rivera alone,” said DeMaria. “Depending on how the judge rules on [the defense’s requests for testimony], that could lead them to wanting to make a deal with Rivera.”

Rivera’s legal team has a track record of exploiting political leverage when evidence-based legal defenses don’t pan out in the courtroom. One of Rivera’s attorneys is David Markus, a renowned Miami defense lawyer who also represents Ghislaine Maxwell, Jeffrey Epstein’s associate and convicted sex trafficker.

As Maxwell’s counsel, Markus has openly proposed a deal with the Trump administration in which his client would receive “clemency” in exchange for being allowed to speak “fully and honestly” about whether the president was involved in any potential sex crimes, or the crimes for which she was convicted.

In a Vanity Fair interview about his work, Markus embraced the ethos of a defense attorney: “I love representing the underdog.”

If David Rivera is an underdog, he’s an underdog with powerful friends in Washington — some of whom may soon be called to testify.