Flávio Bolsonaro fled Brazil on a plane belonging to the fleet of Argentine company Baires Fly, a firm linked to a businessman associated with a convicted drug trafficking conspirator, according to allegations.

The company, tied to an entrepreneur with business links to Federico “Fred” Machado, who faced drug trafficking charges in the US, is also named in a corruption investigation involving disability agency funds under the administration of Javier Milei.

Fórum Investiga, the investigative unit of Revista Fórum, uncovered these connections through court documents and public records in Argentina and the United States.

Sergio Daniel Mastropietro, a commercial broker for Baires Fly, was a business partner of Machado and currently faces money laundering and illicit association charges in connection with the scandal at Argentina’s National Disability Agency (ANDIS).

The company’s role drew scrutiny after the Argentine government confirmed early Wednesday that Bolsonaro entered the country with his wife and two daughters and boarded a private Baires Fly aircraft bound for Guayaquil, Ecuador.

According to Argentina’s National Directorate of Migration, the family crossed the border via the Tancredo Neves International Bridge between Foz do Iguaçu and Puerto Iguazú on Tuesday at 22:50.

The family boarded the plane at 23:30, and the Gulfstream G400, registered as LV-JQW, took off at 00:22 on Wednesday.

The journey followed an order by Federal Supreme Court Justice Alexandre de Moraes seizing Bolsonaro’s passports and barring him from leaving Brazil.

The drug trafficking link traces back to Argentine aviation businessman Federico Andrés Machado, known as Fred Machado, who was accused in the US of participating in an international ring tied to cocaine trafficking and money laundering.

Machado was a partner with Sergio Mastropietro in SO VAIN S.A., a company formed in 2010 for aviation-related ventures. Argentine investigations also documented shared travels, commercial ties, and common Buenos Aires addresses between the two men.

In February 2021, the US Department of Justice unsealed indictments against eight individuals for their roles in an international conspiracy involving narcotics trafficking, money laundering, and financial fraud.

Machado was among those indicted and was identified as an operator engaged in the purchase and sale of aircraft through his firm, South Aviation.

The investigation encompassed a network utilizing US-registered aircraft, several of which were seized in other nations while carrying large shipments of cocaine.

Machado was extradited from Argentina in November 2025 and subsequently reached a plea agreement with US prosecutors.

In August 2026, a federal court in Texas convicted him of conspiracy to commit money laundering and wire fraud.

The initial drug trafficking charge was dismissed as part of that plea agreement.

Machado’s commercial connection is with Mastropietro rather than directly with Baires Fly. The official owner of the company is Luis Grande, who has operated in Argentina’s private aviation sector for decades.

The other scandal involving Baires Fly centres on ANDIS, the agency responsible for providing assistance to people with disabilities in Argentina.

That inquiry examines allegations of contract steering, overbilling, kickbacks, and money laundering in questionable tenders during the Milei administration.

According to documents from the investigation led by federal prosecutor Franco Picardi, two ANDIS providers, Prolite Orthopedics and Probock, transferred 95.06 million Argentine pesos into a Baires Fly bank account on 10 September 2025. That sum represents approximately $62,000 based on exchange rates from 28 October 2026.

The payments occurred after Mastropietro sent the firm’s banking details to Miguel Ángel Calvete, who was identified as one of the figures behind the fraudulent scheme under investigation.

Following those transfers, invoices were issued for the advance purchase of flight hours on company aircraft.

Investigators suspect these commercial transactions were used to lend an appearance of legality to funds derived from irregular public contracts.

Financial tracking uncovered even larger sums. Documents reviewed by Argentine courts show Baires Fly billed five companies tied to the investigated contracts approximately 1.097 billion pesos, or around $720,000, between 2023 and 2025.

This figure reflects registered commercial transactions; it represents a fully confirmed amount of embezzled funds.

On 16 October, federal judge Ariel Lijo ordered formal charges against Mastropietro on suspicion of aggravated money laundering and illicit association.

The ruling also expanded charges against former ANDIS director and former Milei ally Diego Spagnuolo, alongside others allegedly involved in the conspiracy.

Argentina’s Federal Prosecutor’s Office stated that the probe revealed suspected fraud in contracts for medication, prosthetics, and equipment intended for assistance programme beneficiaries.

The airline maintains business relationships with figures across Argentine politics. In November 2023, days after winning the presidential election, Javier Milei used a Baires Fly plane to travel to the US. Luis Grande, the company’s owner, piloted the flight.

In the ANDIS investigation, Mastropietro denied managing Baires Fly or being formally part of the company, saying he acted only as an intermediary arranging aviation services.

The company maintains that it has no connection to the money laundering allegations.

The documents do not show that Bolsonaro was involved in the ANDIS scheme or in any drug trafficking activity.

There is also no evidence that Fred Machado played any role in arranging the flight.

In the United States, the Trump administration has unveiled its plan to support electoral reforms in Venezuela and lead the country toward presidential elections.

US Secretary of State Marco Rubio told international journalists during a press conference on Monday that Venezuela’s current electoral infrastructure was “designed to rig elections”.

As the chief architect of the administration’s Venezuela policy, Rubio argued that this system must be overhauled quickly to enable a valid vote.

According to Rubio, talks between the government of Interim President Delcy Rodríguez and opposition factions led by Dinorah Figuera are moving toward a concrete timetable.

The sides are preparing to appoint a new Supreme Tribunal of Justice (TSJ) before the end of the year, followed immediately by the renewal of the National Electoral Council (CNE).

“We obviously need to use our leverage over the interim Venezuelan authorities to ensure that the process moves forward responsibly. Our goal is to hold elections,” Rubio said, welcoming what he described as “serious progress” in that direction.

The US secretary issued a warning, saying, “Whoever tries to derail the process will do serious damage to Venezuela.”

Speaking at a separate press briefing, an unnamed senior US Department of State official outlined the step to follow institutional renewal, according to a report by the Venezuelanalysis portal.

According to the official, once both the TSJ and the CNE are reconstituted, the Venezuelan presidency will be declared permanently vacant, triggering a constitutional six-month window to conduct elections under “competitive conditions”.

The same official stressed that political guarantees must be provided and media access rules regulated during this phase.

Advocating the inclusion of pro-government factions in the “transitional period”, the official said peaceful democratic transitions often require the cooperation of outgoing groups, citing Spain and Portugal as precedents.

Electoral timetable and judicial work accelerate

Asked about a definite election date, Rubio said the Rodríguez administration had complied with US timelines so far.

Emphasising that they would not wait two years for an election, Rubio said: “That is not going to happen. In the best-case scenario, I have two years and two months left in this job.”

Rubio’s remarks coincided with statements by Dinorah Figuera, who heads the opposition delegation in the negotiations with government representatives.

Figuera had predicted that presidential elections would take place in late 2027 or early 2028.

Meanwhile, during the third round of political dialogue in Venezuela, the parties agreed to review four pieces of legislation governing political participation, pluralism, and the autonomy of political organisations, including the Law on Political Parties, Public Meetings, and Demonstrations.

The discussions also addressed disqualifications from public office and the examination of legal frameworks governing political rights.

In parallel, Venezuela’s National Assembly officially initiated the process to renew all 32 justices of the Supreme Tribunal of Justice.

Applications from legal professionals seeking seats on the court will be accepted from Wednesday, 28 October until Wednesday, 11 November. The fourth round of dialogue is scheduled for 11 to 15 November.

Rodríguez and other senior Venezuelan officials have not yet commented on the US Department of State’s statements.

Machado’s return and convoy controversy

The White House’s assertions regarding Venezuelan reforms and elections coincided with the return of far-right opposition leader María Corina Machado to the country on Sunday.

Supporters of Machado, who had lived abroad for more than a year, called for their leader to be included in the ongoing negotiations.

Responding to questions about Machado’s return, Rubio said he had told the Rodríguez government “weeks ago” that she should be allowed to return to the country unhindered.

Denying claims that Washington obstructed Machado’s return, the Secretary of State said the opposition leader had merely been advised not to travel immediately following the twin earthquakes on 24 June.

Interim President Rodríguez, however, criticised the manner of the opposition politician’s return.

Characterising it as a “show” that could have been avoided, Rodríguez addressed Machado’s journey to Caracas at the head of a vehicular convoy covering 400 kilometres, following her appearance at a church in Lara state amid chants of “freedom” and calls for immediate presidential elections.

“The airports are right there. Let us stop putting on a show. Many people who benefited from this process aimed at peaceful coexistence and from the amnesty law were able to enter the country through the airport’s new transit structures,” Rodríguez said.

The interim president declined to reveal which route Machado had used to re-enter Venezuela.

Machado, who in recent years backed economic sanctions against Venezuela as well as foreign military intervention, left the country in December 2024 to travel to Oslo to receive the Nobel Peace Prize, which she subsequently dedicated as a gift to Trump.

While Machado and her party maintain that the government had previously barred her from returning seven times, Venezuelan authorities deny the allegation.

Asked whether the judiciary would act against Machado, Rodríguez said she hoped to see “remorse and a change of direction” from the opposition figure, adding that the opposition leader could make “some contribution to the country”.

Brazilian Senator Flávio Bolsonaro fled his country following his defeat in the presidential election and arrived in Miami on Tuesday.

According to a report by the O Globo newspaper, Bolsonaro was met upon his arrival in the US by his brother Eduardo.

Eduardo had moved to the US last year to lobby President Donald Trump to assist their father, former President Jair Bolsonaro, who was convicted of plotting a coup, and had lived there ever since.

A senior State Department official said early Tuesday that the US would grant visas to Flávio and his family.

Facing multiple criminal investigations in Brazil, Flávio Bolsonaro had been ordered to surrender his passports to the Federal Police by Tuesday, but failed to do so, according to a police official familiar with the matter.

Supreme Court Justice Alexandre de Moraes, whom the Bolsonaro family has long accused of political persecution, had demanded the surrender of the documents out of concern that the senator was a flight risk.

Bolsonaro’s loss to Luiz Inácio Lula da Silva in Sunday’s runoff election dealt a heavy blow to the family, which had sought to establish a political dynasty in Brazil.

The senator had made the release of his father Jair Bolsonaro, who was sentenced to 27 years in prison for plotting a coup after his 2022 election defeat, the central theme of his campaign.

Speaking to reporters early Wednesday after returning from a campaign trip in Texas, Trump said he would approve Bolsonaro’s entry into the US, though he added that he thought Bolsonaro was in Argentina.

Speaking in Texas on Tuesday afternoon, Trump avoided mentioning Bolsonaro, but repeated his unsubstantiated claims that the Brazilian election was rigged.

After criticizing Democrats as “the biggest election riggers”, Trump added, “Brazil is pretty good at that too.”

The US leader has long been an ally of the Bolsonaro family and had imposed tariffs on Brazilian goods last year in an unsuccessful attempt to help Jair Bolsonaro avoid prosecution in his coup case.

The Trump administration did not officially endorse Bolsonaro’s presidential bid. However, according to The New York Times, the State Department under Secretary of State Marco Rubio had worked behind the scenes ahead of the vote to strengthen Bolsonaro’s standing in Brazil.

On Tuesday morning, neither the police nor allies had any information regarding Flávio Bolsonaro’s whereabouts, after Infobae reported that he had crossed into Argentina and planned to travel to the US from there.

Brazilian police have no official record of Bolsonaro leaving Brazil, and the spokesperson for Argentine President Javier Milei denied that Flávio Bolsonaro had entered the country.

Several Bolsonaro allies told Bloomberg that they had tried to contact him but received no response.

“Fleeing Brazil is a disgraceful act,” Lula said at an event celebrating his 81st birthday.

Bolsonaro faces at least two federal investigations into money laundering allegations, one of which stems from his ties to the former owner of Banco Master SA, who was implicated in the largest bank fraud case in Brazil’s history.

The elder Jair Bolsonaro had also left for the US following his election defeat. He returned months later and was barred from holding public office for eight years for spreading false claims about Brazil’s electronic voting system ahead of the election, before later being convicted of plotting a coup.

On Monday, Flávio Bolsonaro abandoned plans to challenge the election results and posted a social media video stating that the Supreme Court had barred him from leaving Brazil.

Meanwhile, according to sources familiar with the matter who spoke on condition of anonymity to discuss private conversations, Moraes’s decision caused unease among members of the Supreme Court as well as officials in Lula’s government.

According to those sources, the Lula administration had wanted to focus on calming the country and moving past the polarization that flared during back-to-back electoral battles between the leftist leader and a member of the Bolsonaro family.

The administration viewed the move by Moraes, a polarizing justice who presided over Jair Bolsonaro’s case and has long faced censorship accusations from the Brazilian right, as counter to those aims.

Early Tuesday, Supreme Court Justice Flávio Dino ordered federal authorities to investigate possible illegal foreign funding for Bolsonaro’s presidential campaign, including through a group linked to US Vice President JD Vance.

The justice emphasized that the order did not prove illegal foreign funding had taken place, but noted that allegations raised during Brazil’s presidential campaign warranted an investigation.

Speaking at a press conference on Tuesday, Argentine government spokesperson Adrian Ravier said Bolsonaro had not requested asylum in Argentina.