Will Trump announce a trade deal with Cuba?

Senator Marco Rubio is a primary foreign policy advisor on Latin America. He has been identified as a central figure in Donald Trump's considerations, particularly regarding Cuba. During the Trump administration, Rubio was characterized as Trump's "top negotiator" on Cuba, despite also being described historically as "Cuba’s loudest foe" ^[1]. This reflects his long-standing hawkish stance against the Cuban regime and his consistent opposition to lifting the Cuba embargo ^[1]. The Trump administration's policy, which Rubio influenced, pursued a "maximum pressure" campaign against Cuba, involving historic sanctions, threats, and an oil blockade ^[4].

Conservative organizations like The Heritage Foundation support firm action on Cuba. This stance aligns with the "maximum pressure" approach, as The Heritage Foundation has consistently advocated for robust measures against the Cuban government. They applauded the Trump administration for implementing historic Cuba sanctions and called for steps to cut the regime's profit ^[2]. Furthermore, The Heritage Foundation has published calls for the U.S. to "intervene in Cuba and save the island nation," directly reflecting a position that opposes easing restrictions or lifting the embargo ^[3]. While the research did not identify specific individuals from the America First Policy Institute as primary foreign policy advisors on Latin America with documented stances on the Cuba embargo, The Heritage Foundation's institutional position clearly supports policies contrary to lifting it.

Influential Cuban-American political groups strongly oppose trade with the current regime. Political action committees and prominent groups in South Florida consistently express a hardline stance against any potential trade deal with the current Cuban government. Their public statements and editorials frequently emphasize a desire for 'regime change, not negotiations' ^[1] and explicitly demand 'freedom, not a deal' for the Cuban people ^[3]. This position is further reinforced by a persistent call for 'justice for the Cuban people' before any engagement is considered ^[4].

Business groups seek future Cuban economic engagement only under democratic conditions. Sentiment among Cuban-American business groups in South Florida during Q1 and Q2 2026 indicates an aspirational interest in future economic engagement with Cuba, but only if specific political prerequisites are met. These businessmen discussed investing in a free, democratic Cuba, explicitly distinguishing this from engaging with the existing communist government ^[2]. This demonstrates that while there is an interest in investment, it is entirely contingent upon a fundamental transformation to a democratic system, rather than a willingness to support trade deals with the current government ^[5].

Cuba initiated economic liberalizations, aiming to boost investment and national economy. Since late 2025, the Cuban government has introduced specific measures intended to foster economic growth and flexibility. This follows a broader strategic effort outlined in a government program approved on February 3, 2025, designed to correct economic distortions and boost the economy throughout that year ^[4]. Consistent with this, state-run media, such as Granma, reported on November 28, 2025, the announcement of measures to make foreign investment more flexible and dynamic ^[1]. Further steps were unveiled on March 17, 2026, to facilitate the participation of Cubans residing abroad in the national economy ^[2].

Prisoner releases, alongside economic shifts, may prompt renewed U.S. trade talks. In terms of human rights, independent monitoring groups and news outlets have reported actions that could be framed as concessions. On April 3, 2026, Reuters reported that Cuba began releasing prisoners, a development that garnered scrutiny from human rights organizations and the U.S. government ^[3]. On the same day, Amnesty International issued a statement reiterating its call for Cuban authorities to release individuals detained for political reasons, acknowledging the context of these recent releases ^[5]. These human rights concessions, coupled with the economic liberalizations, represent actions by the Cuban government that could potentially be cited as a basis for renewed U.S. engagement in trade negotiations.

Based on available SEC filings and lobbying disclosures from H1 2026, there is no clear evidence of a significant increase in 'Cuba'-related expenditures from major U.S. agricultural, travel, or port-related corporations. In the agricultural sector, U.S. Ag/Food Exports to Cuba actually decreased by 21.7% in January 2026 compared to the previous year, suggesting a decline in economic engagement rather than an increase ^[1]. Lobbying efforts by groups like the American Sugarbeet Growers Association focused on general 'Farm Policy' ^[3], and a Senate Ag Committee lobbying blitz centered on a 'Domestic Consumption Push,' without specific mentions of 'Cuba' ^[4].

Travel industry lobbying disclosures lacked specific 'Cuba' references. Royal Caribbean Cruises Ltd. filed SEC documents in January 2026, including an 8-K related to 2025 earnings ^[5]. While the company's lobbying activities disclosed expenditures of US$90,000 ^[2] and an additional US$30,000 through a lobbying firm ^[6], these public disclosures do not specify that these lobbying efforts were directed towards issues related to 'Cuba' ^[2].

No broad corporate push for Cuba normalization was evident. No information was available for Cargill or the Port of New Orleans in relation to 'Cuba'-specific expenditures or lobbying during H1 2026, further indicating no significant corporate push for normalization with Cuba during this period.

The 56th OAS General Assembly is the key mid-2026 diplomatic engagement. The 56th Regular Session of the Organization of American States (OAS) General Assembly is scheduled for June 23-25, 2026, in Asunción, Paraguay. This annual gathering represents the most prominent high-level U.S. diplomatic engagement in mid-2026 suitable for preliminary discussions or a pre-announcement regarding a shift in Cuba policy. It offers a significant platform for U.S. diplomatic engagement, including opportunities for high-level bilateral meetings where potential policy shifts, particularly concerning trade, could be hinted at before a more detailed official announcement ^[1].

President Trump already signaled Cuba policy changes at an earlier summit. The 10th Summit of the Americas, held from March 6-8, 2026, in Santa Marta, Colombia, previously served as a venue for U.S. President Donald Trump to signal potential policy changes toward Cuba. During this summit, Trump's remarks on March 8, 2026, highlighted that "change is coming" for Cuba and that his administration was "exploring all options" to foster democracy and economic engagement ^[3]. Such high-level diplomatic forums, like the Summit of the Americas or OAS meetings, inherently provide logical venues for signaling major foreign policy directions before formal deals are finalized ^[2].