On September 14, 2025, Cuba stands at a crossroads unlike any it has faced in its tumultuous, 66-year post-revolutionary history. The island nation, once celebrated for its resilience in the face of adversity, now finds itself gripped by a crisis so deep and multifaceted that even seasoned Cuba-watchers are hesitant to predict its outcome. The storm clouds gathering over Havana are not just economic or political—they are existential, threatening to upend the very fabric of Cuban society and its relationship with the United States.
For decades, the Cuban communist regime has weathered storms that would have toppled less entrenched governments. According to E-International Relations, the regime survived the 1961 Bay of Pigs invasion, the Mariel Boatlift of 1980, the withdrawal of Soviet support in the early 1990s, and the painful Special Period that followed. Even the death of Fidel Castro in 2016 and the unprecedented mass protests of July 2021 did not loosen the Communist Party’s grip on power. Yet, as the historian notes, the current emergency is more complex than any before, with fewer tools left in the regime’s survival kit.
What makes 2025 different? The answer lies in a perfect storm of internal decay and external pressure. Food and fuel shortages have reached catastrophic levels. According to a recent report by the international Food Monitor Program, a staggering 25% of Cubans now admit to going to bed hungry, and malnutrition is on the rise. Two-thirds of the population blame their own government for the worsening shortages, a damning statistic for leaders who once promised abundance. Cuba, once the jewel of the Caribbean, now accounts for 40% of the region’s food insecurity cases, despite only holding 5% of its population. The island imports 70% of its food—much of it from the United States—but lacks the funds and credit to buy more. Transportation, refrigeration, and distribution systems are in shambles, and hospitals sometimes go without power or water.
The situation is compounded by a fuel crisis that has left buses, trucks, and even trash collectors stranded. Blackouts are routine, and the collapse of infrastructure is so severe that building collapses in Havana have become tragically commonplace. As E-International Relations describes, the city once known for its architectural beauty is now a landscape of ruins and scaffolding. Meanwhile, the regime’s elite flaunt their privilege, with luxury hotels and extravagant events standing in stark contrast to the daily struggles of ordinary Cubans. This disconnect has fueled public anger, even among longtime supporters of the revolution.
On the political front, President Miguel Díaz-Canel faces mounting challenges. Unlike the revolutionary generation of the Castros and Che Guevara, Díaz-Canel lacks the credentials and charisma to inspire loyalty. His government is increasingly seen as arrogant and out of touch, serving as a lightning rod for popular frustration. The military, long the backbone of the regime, now controls an estimated 70% of the economy through the GAESA conglomerate. Secret financial documents leaked to the Miami Herald in 2024 revealed a hard currency stash of $18 billion, even as ordinary Cubans sink deeper into poverty.
Demographically, the island is hemorrhaging people. Over one million Cubans emigrated between 2020 and 2023, with another quarter million leaving in 2024. Most headed for the United States, often by crossing the border with Mexico. This exodus, the largest in Cuban history, has left the population older, smaller, and less economically viable. The so-called "Cubanos con Fé"—those with family abroad—are increasingly privileged, while those left behind struggle with a near-worthless currency and dwindling resources.
Against this backdrop, the return of Donald Trump to the White House in January 2025 has added a new layer of complexity. According to El País, Trump’s administration has implemented a "total pressure embargo" on Cuba, rolling back the Biden-era immigration provisions that allowed over 600,000 Cubans to enter the U.S. since 2022. The migration valve that once served as a safety release for the regime is now firmly shut. Deportations have surged, with 4,248 Cubans sent back to the island in recent months—the highest number ever recorded. Another 42,084 face final deportation orders, and nearly 550,000 remain in legal limbo, unable to regularize their status.
For many Cuban-Americans in Florida, the political landscape is fraught with contradictions. In the 2024 presidential election, 68% of Cuban-Americans in the state voted for Trump, hoping for economic revival and firm opposition to the Cuban regime. Yet, as the months have passed, some have grown disillusioned. Jessica Ruiz, a former supporter, told El País, "Instead of feeling more security and progress, I’ve seen an environment of division, decisions that don’t always favor ordinary workers, and an economy that hasn’t felt as strong as he promised." Still, as Guillermo Grenier of Florida International University notes, most voters would make the same choice if the election were held today, despite worsening economic conditions.
Meanwhile, the Trump administration—guided by Cuban-American Secretary of State Marco Rubio—has made no secret of its desire to topple the communist regime. Rubio has pushed for aggressive action, including compiling lists of former Cuban officials now living in the U.S. and advocating for a total ban on travel and remittances to the island. The administration’s focus on Cuba, however, is balanced by other foreign policy priorities, and some members of the Republican coalition are wary of military intervention.
For Cubans on both sides of the Florida Straits, fear and uncertainty are the order of the day. The Cuban Adjustment Act of 1966, which has long offered a path to legal status for Cubans in the U.S., remains in place for now. Attorney Liudmila Marcelo told El País that while there is "no imminent risk" of its repeal, the atmosphere of panic is palpable. "It’s a way to sow panic and gather supporters for local political campaigns," she said, emphasizing that the law is "ironclad" and could only be repealed by a consensus in Congress and the announcement of free elections in Cuba.
Back in Havana, the regime’s options are dwindling. Its old lifelines—support from the Soviet Union, Venezuela, and foreign investors—have all but dried up. With credit exhausted and foreign investment evaporating, the government’s ability to impose further austerity is limited. The population, already squeezed to the breaking point, may not tolerate more deprivation. Political purges and repression remain tools of last resort, but as E-International Relations cautions, there are "not enough emergency boats" left to save everyone if the ship goes down.
In this climate, the future of Cuba hangs in the balance. The regime’s legendary resilience faces its greatest test yet, and the outcome is anything but certain. For now, the world watches and waits, wondering whether Cuba’s long twilight will finally give way to a new dawn—or a darker night.