Trump and Rubio allies compete for Cuban assets as foreign firms exit

Trump Organization executives returned to Cuba through Dominari Holdings

A growing circle of Washington and Florida insiders aligned with President Trump and Secretary of State Marco Rubio are jockeying for control of Cuban assets and collecting fees to help clients navigate the administration’s sanctions regime, The Guardian reported Thursday. The Guardian’s reporting details how Trump allies, Rubio-linked lobbyists, and Cuban exiles have positioned themselves for lucrative business opportunities if Cuba’s one-party state collapses, even as foreign companies are driven out of the island.

Since Trump signed an executive order on 1 May driving Canada’s Sherritt International from its nickel and cobalt mining joint venture with the Cuban state, two rival US bids to buy out the Canadian firm’s stake have been presented to US authorities. On one side is Ray Washburne, vice-chair of Trump’s 2016 Victory Committee and organizer of last week’s Republican Midterm Convention in Dallas. On the other is Albert Huddleston, another Texas oil tycoon with close ties to the White House. Both are hoping to swoop in despite nine-figure claims on Sherritt’s Cuban holdings by Citigroup and Office Depot. Washburne did not respond to The Guardian; a consortium group including Huddleston declined to comment.

A similar pattern has played out at a Cuban copper-gold mine operated as a joint venture with the Cuban state by Australia’s Antilles Gold Ltd. After being blacklisted over its Cuba operations in June, Antilles received approval from the Trump administration to negotiate the transfer of its stake to Global Emerging Markets, a New York-based multibillion-dollar investment fund.

“If I had done during the Biden administration what Trump’s friends have done now, I’d have been put in jail,” said a person with several decades of experience in Cuba policy who requested anonymity.

Trump Organization executives who previously traveled to Cuba to explore real estate deals and who registered the Trump trademark there in 2008 have in recent months returned to the island under the aegis of Dominari Holdings, according to sources cited by The Guardian. The executives reportedly met with Raúl Guillermo Rodríguez Castro, the grandson of former Cuban president Raúl Castro and known as “the Crab,” to explore opportunities as Spanish hotel giants Meliá and Iberostar ended decades-long operations on the island. Neither Antilles nor Dominari returned calls for comment.

Continental Strategy, a Washington lobbying firm led by Cuban-American allies of Rubio who oversaw the maximum-pressure Cuba policy as officials in the first Trump administration, has emerged as a key intermediary. The firm’s executives include Carlos Trujillo, Trump’s former ambassador to the Organization of American States; John Barsa, Trump’s former acting USAID administrator; and Alberto Martinez, Rubio’s former chief of staff. In July, the firm registered to represent Madrid-based Vima World SL, a food industry player that partners with GAESA, the Cuban military conglomerate that has become the main target of US sanctions. Continental terminated its contract with Vima this month after netting nearly $40,000, according to corporate disclosures. The firm has also represented MasTec, the telecom company owned by Rubio associate Jorge Mas Santos; American Sugar Refineries, owned by Trump-ballroom donor and Rubio patron Pepe Fanjul; and General Cigar Co, which is fighting Cuba’s state tobacco enterprise in US court over the Cohiba cigar trademark.

“It’s been interesting to watch how quickly some hardline ideologues become pragmatists once there’s money on the table,” one person familiar with the contract told The Guardian, noting that Continental has taken on other Spanish firms with Cuban business interests “trying to get on the right side of sanctions, like banks and hotel chains.”

Cubans have lived under an effective fuel blockade since January 2026, when the Trump administration cut oil shipments to the island from Cuba’s main ally after the capture of Venezuelan President Nicolás Maduro; the administration has since blocked oil deliveries from Mexico by threatening tariffs on any country sending petroleum to the island. Treasury-authorized oil exports from Florida and Texas to Cuba’s private sector — nearly nonexistent last year — have surged to over $160 million so far this year.

Florida shipping lines appear to be benefiting from the rerouting. Crowley, a donor to Cuban-American Republican lawmakers María Elvira-Salazar and Mario Díaz-Balart, has seen fresh business as foreign shippers have been hit by sanctions and Cuba-bound commerce has been forced to route through Florida, informed sources told The Guardian. Crowley declined to comment.

UN human rights experts have warned that Washington’s latest measures “knowingly deprive a population of the means to survive.” Franklin Graham, the Trump-allied CEO of evangelical aid organization Samaritan’s Purse, recently secured a $40 million federal contract to distribute humanitarian aid in Cuba, despite lacking the capacity to implement such a contract on the island, according to sources familiar with the matter. A Samaritan’s Purse spokesperson said: “Details about aid for Cuba are still being developed and are not yet finalized.”

Other organizations with longstanding federal funding have capitalized on the administration’s Cuba push. A newly formed group of former employees of the US taxpayer-funded Foundation for Human Rights in Cuba (FHRC), along with longtime Republican lobbyist Otto Reich and the husband of top Rubio state department aide Viviana Bovo, filed lobbying disclosures in July indicating the group is “advising [the] State Department on [an] economic development plan for a future free and democratic Cuba, including energy-sector development and compensation for owners of property/business expropriated by the Cuban government.” Reich and FHRC chairman Tony Costa are involved in efforts to mobilize billions of dollars in private investment from Cuban exiles for a post-communist Cuba through the newly created Cuban-American National Chamber of Commerce.

FHRC and another attendee of the CANCC gatherings, Armando Labrador, a Miami-based plastic surgeon who regularly meets with state department officials and wants to become Cuba’s next leader, have paid DC lobbying firm The Cormac Group a combined $100,000 since December.

Just before the July release of a heavily criticized State Department report that referred to Cuba as a nearby terror hub plotting to conquer the United States, Digital News Association Inc received a fresh $250,000 contract from the US government’s Office of Cuba Broadcasting for “investigative journalism, research and media production,” after which its main site launched an online interview series repeating Trump administration claims of Cuba’s purported threat to US national security.

Vima, Continental, The Cormac Group, and Digital News did not return calls for comment to The Guardian.

“The cause is regime change,” said Erik Cartelle, a consultant working to connect prominent Cuban exiles with Rubio’s State Department. “I have clients that want to do a lot of business in Cuba, and the administration is banking on Cuban-Americans going to Cuba and investing, but if there’s a deal that’s going to be had with the regime, it needs to take into account the diaspora’s wishes. You’ve got to listen to this community.”

Rubio told Axios last month there are “no escape valves” from the administration’s pressure campaign against Cuba.

The asset jockeying follows the May executive order and expanded sanctions that drove foreign companies including Sherritt, Meliá, and Iberostar from Cuba, as MSI previously reported in Foreign Businesses Abandon Cuba as Economy Collapses Under US Sanctions. The pressure campaign then widened with sanctions on five Cuban state firms and a Castro family member, as MSI reported later that month.