Trump Suggests Cuba as Next Stop After Iran: ‘Free Cuba Now’ Movement Gains Momentum

Donald Trump stated on July 1, 2026, that the United States would address Cuba as the “next stop” for policy action following the administration’s current efforts regarding Iran. The remarks were delivered during the inauguration of the Theodore Roosevelt Presidential Library, linking current foreign policy objectives to the legacy of U.S. territorial expansion.

Speaking at the event, Trump indicated a sequential approach to his administration’s foreign priorities. He stated, "We can go through Cuba after, Cuba is the next stop," specifying that this transition would occur once the administration’s dealings with Iran were complete.

The comments were made in the context of a ceremony honoring the 26th U.S. president, Theodore Roosevelt. The choice of venue highlights a thematic connection between the current administration’s rhetoric and the expansionist policies of the early 20th century.

The administration has not yet released a specific timeline or a detailed policy framework for the proposed actions regarding Cuba. However, the phrasing suggests that Cuba remains a primary target for U.S. diplomatic or economic pressure following the resolution of Iranian affairs.

The mentions of Cuba and Iran as sequential targets mirror a strategy of focused, one-on-one diplomatic pressure. This approach contrasts with multilateral strategies that address multiple regional conflicts or diplomatic disputes simultaneously.

Why was this remark made at a Theodore Roosevelt event?

Theodore Roosevelt’s presidency was defined by the “Big Stick” policy, a foreign policy approach summarized by the phrase “speak softly and carry a big stick.” This doctrine advocated for the exercise of diplomatic pressure backed by the credible threat of military force, particularly in the Western Hemisphere.

By referencing Cuba at the inauguration of Roosevelt’s library, the current administration invokes a period of history when the U.S. actively expanded its influence and territory. Roosevelt’s tenure saw the U.S. solidify its role as a global power through strategic interventions and the acquisition of overseas territories.

The “Big Stick” era established the precedent for U.S. intervention in Latin American and Caribbean affairs. This historical framework provides the context for Trump’s description of Cuba as a “stop” on a broader geopolitical itinerary.

What is the historical precedent for U.S. territorial expansion in the region?

The U.S. expansionist drive during the Roosevelt era was rooted in the outcomes of the Spanish-American War of 1898. This conflict resulted in the U.S. acquiring several territories that fundamentally altered its global footprint.

Under the Treaty of Paris, the United States gained control over several key locations:

• Puerto Rico: Acquired from Spain, it became an unincorporated territory of the U.S.
• Guam: A strategic Pacific island that provided the U.S. with a critical naval outpost.
• The Philippines: Annexed by the U.S., leading to a period of colonial administration and the Philippine-American War.

These acquisitions were intended to secure trade routes to Asia and establish a permanent U.S. presence in the Pacific and Caribbean. Roosevelt expanded this strategy by overseeing the construction of the Panama Canal, which allowed the U.S. Navy to move rapidly between the Atlantic and Pacific Oceans.

The annexation of these territories created a model of “strategic depth” that Roosevelt used to project power. Trump’s current rhetoric regarding Cuba reflects a similar focus on the Caribbean as a zone of essential U.S. interest.

How does this compare to early 20th-century expansion?

There is a distinct difference between the territorial annexation of the Roosevelt era and the policy goals of the current administration. While Roosevelt focused on the physical acquisition of land and the establishment of colonies, the current administration’s focus is on political and economic alignment.

Roosevelt’s expansionism was characterized by formal annexation and direct colonial governance. In contrast, the current administration’s “next stop” approach toward Cuba suggests a focus on regime pressure or the implementation of strict sanctions to achieve political outcomes.

Despite these differences, both eras share a common thread of unilateralism. Roosevelt’s Roosevelt Corollary to the Monroe Doctrine asserted that the U.S. had the right to intervene in the affairs of nations in the Western Hemisphere to maintain stability. Trump’s sequence of addressing Iran and then Cuba reflects a similar belief in the U.S. right to unilaterally determine the terms of engagement with sovereign nations.

The focus on Cuba follows a long history of U.S. efforts to influence the island’s governance, ranging from the Platt Amendment of 1901, which gave the U.S. the right to intervene in Cuban affairs, to the comprehensive embargo maintained for decades.

As the administration concludes its current priorities with Iran, the stated focus on Cuba indicates that the Caribbean will remain a central pillar of U.S. foreign policy in the coming period.