Trump and Rubio Allies Vie for Control of Assets as US Sanctions Pressure Cuba

As the United States intensifies its economic pressure campaign against Cuba, an array of Washington and Florida insiders, billionaire allies of Donald Trump, and lobbyists connected to Secretary of State Marco Rubio are positioning themselves for potential business opportunities and jockeying for control of the island nation's assets in the event of a regime collapse. The developments follow a wave of new secondary sanctions that have driven scores of foreign companies, including Spanish hotel chains, a Canadian mining firm, European shipping giants, and financial institutions, out of Cuba over the summer.

Secretary of State Marco Rubio stated last month that there are no escape valves from the unprecedented pressure campaign. However, while foreign enterprises retreat, a growing cast of American business figures, political donors, and Cuban exiles are charging top dollar to help clients navigate the expanding web of sanctions.

Among the high-profile maneuvers are competing US bids to buy out Canada-based Sherritt International’s stake in a nickel and cobalt mining joint venture with the Cuban state, following an executive order signed by Donald Trump on May 1. Ray Washburne, vice-chair of Trump’s 2016 Victory Committee, is reportedly clashing with Texas oil tycoon Albert Huddleston over the potential acquisitions, despite nine-figure claims on Sherritt’s holdings by Fortune 500 corporations Citigroup and Office Depot. Additionally, Australia’s Antilles Gold Ltd received approval from the Trump administration to negotiate the transfer of its stake in a Cuban copper-gold mine to the New York-based investment fund Global Emerging Markets after being blacklisted in June.

Sources indicate that executives from the Trump Organization have also returned to Cuba under the aegis of Dominari Holdings to explore real estate and other opportunities amid the departure of long-standing Spanish hotel operators Meliá and Iberostar. These executives reportedly met with Raúl Guillermo Rodríguez Castro, the grandson of former Cuban president Raúl Castro.

American investors are not the only beneficiaries of the shifting economic landscape. Cuba has faced an effective fuel blockade since January 2026, when the Trump administration halted oil shipments from Venezuela following the abduction of President Nicolás Maduro, and subsequently blocked deliveries from Mexico through tariff threats. Conversely, Treasury-authorized oil exports from Florida and Texas to Cuba's private sector have surged to over $160m this year. Florida shipping lines, including Crowley—a donor to Florida Republican lawmakers Mario Díaz-Balart and María Elvira-Salazar—appear to benefit from sanctions that have forced Cuba-bound commerce to reroute through Florida.

Humanitarian aid and contracting have also drawn scrutiny. Franklin Graham, CEO of the evangelical aid organization Samaritan's Purse, recently secured a $40m federal contract to distribute humanitarian aid in Cuba, despite questions regarding the organization's operational capacity on the island. Meanwhile, UN human rights experts have warned that Washington's measures risk depriving the population of basic survival means.

Ironies have emerged within the lobbying sphere as well. In July, Madrid-based Vima World SL, a leading food industry player partnered with the Cuban military conglomerate GAESA, hired Continental Strategy. The top Washington lobbying firm is led by Cuban-American allies of Rubio who managed Cuba policy during the first Trump administration, including Carlos Trujillo, John Barsa, and Alberto Martinez. Continental reportedly terminated the contract this month after netting nearly $40,000, having previously represented clients staunchly opposed to the Cuban government, such as MasTec, American Sugar Refineries, and General Cigar Co.

Other organizations are likewise capitalizing on the administration's push for political and economic transformation. A newly formed group involving former employees of the Foundation for Human Rights in Cuba (FHRC), longtime lobbyist Otto Reich, and associates of State Department aide Viviana Bovo has filed disclosures indicating it is advising the State Department on an economic development plan for a future democratic Cuba. Meanwhile, the FHRC and Miami plastic surgeon Armando Labrador have funneled funds to DC lobbying firm The Cormac Group to advance their priorities before Washington officials.

Federal grants and contracts have similarly flowed to other entities. Digital News Association Inc secured a $250,000 contract from the US government’s Office of Cuba Broadcasting for investigative journalism and media production, following a State Department report that characterized Cuba as a regional security threat.

Consultants working with the diaspora emphasize that the broader objective remains regime change, noting that any future economic engagement must account for the wishes and investments of the Cuban-American community as the administration presses forward with its containment and pressure strategies.