The Cuban Regime Is Shaking

Dear all,

We welcome you to the Greater Caribbean Monitor (GCaM).

The war in Iran has not de-escalated. Our main analysis in Iran this week is the Strait of Hormuz, which has been hot this week and has also hurt your pockets with those gas prices. The war, however, seems to be reaching a dangerous point that suggests it will not end if there aren’t boots on the ground eventually. We will approach this next week, since the Greater Caribbean Monitor has to go back to the Greater Caribbean for a moment. Cuba, this time, is the focus of our attention.

As Miguel Díaz-Canel announced diplomatic negotiations with the U.S., the world reacted in the hopes of a democratic transition. Let me tell you now: that won’t happen. At least, not through diplomacy. Venezuela provided sufficient evidence to the Biden Administration that a democratic process will not be guaranteed through sanction relief and goodwill alone. Trump, I believe, has learned from that horrible mistake his so-criticized naive predecessor made.

What is evident, however, is that Cuba has never faced a crisis like this one. Not only due to the severity of the oil situation, but also due to the lack of options or allies to give a helping hand… and none seem to emerge over the horizon. That does not translate to a democratic transition, but the regime is certainly cornered, and Trump—or more specifically, Rubio— won’t let that opportunity go.

In this issue, you will find:

• Cuba Is on the Brink of Collapse… Or Is It?

• The Biggest Losers in the Strait

• Valencia Tightens the Race: Colombia’s Elections Prospects

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With regime change being the center of Trump’s foreign policy in 2026, Cubans are starting to see some light at the end of the tunnel, but that might not be enough.

In perspective. Cuba is entering one of the most turbulent moments in its contemporary history, as a series of pressures converge on a political system that has remained largely unchanged since 1959. The island is experiencing a severe energy crisis after the interruption of crucial oil flows that once sustained its electricity grid. Venezuelan shipments collapsed following the fall of Nicolás Maduro, while Mexican supplies were suspended under pressure from Washington. The consequences have been immediate and visible: prolonged blackouts, failing infrastructure, and widespread shortages of fuel and basic goods.

• These conditions have fueled a wave of protests that, while still limited in scale, have reached a level of political symbolism rarely seen in Cuba.

• Demonstrators have not only protested blackouts and living conditions but have also attacked and burned Communist Party buildings—an extraordinary escalation in a system where dissent traditionally avoids direct confrontation with regime institutions.

• At the same time, Havana has publicly acknowledged for the first time that it is holding talks with the U.S., while allowing limited cooperation with the FBI in security investigations. Taken together, the combination of economic collapse, growing unrest, and diplomatic maneuvering suggests a regime under exceptional stress.

Between the lines. Behind the scenes, U.S. diplomacy has played a more active role in shaping this moment than is immediately visible. Secretary of State Marco Rubio has been central to Washington’s strategy toward the island, quietly pursuing channels that bypass the formal Cuban government and instead reach figures within the regime’s inner circle. Reports of contacts involving members of the Castro family network illustrate an approach designed not to provoke sudden collapse but to encourage the possibility of change from within the system itself.

• For Rubio, the issue carries both strategic and personal significance. As the son of Cuban exiles and one of the most prominent advocates of hardline policy toward Havana, he has long argued that the communist government represents the last major authoritarian holdover in the Western Hemisphere.

• His efforts reflect a broader calculation inside the current U.S. administration. If political transformation in Cuba is to occur, it will likely emerge through negotiations and pressure directed at the regime’s own elite rather than through external intervention.

• The same happened in Venezuela, and in that scenario, it was both Rubio’s own interest in the cause as well as his persuasion over Trump that made it happen.

Down memory lane. History, however, offers reasons for caution before declaring the Cuban government close to collapse. The regime has survived previous crises that appeared existential at the time. The most severe was the “Special Period” of the early 1990s, when the collapse of the Soviet Union eliminated Cuba’s primary economic patron and plunged the island into extreme hardship. Blackouts were widespread, food shortages were severe, and social unrest culminated in the 1994 Maleconazo protests in Havana. Yet the government endured, largely because the political elite remained united and the security apparatus retained control.

• More recently, the nationwide protests of July 11, 2021, represented the largest wave of demonstrations since the revolution itself.

• Thousands of people took to the streets across dozens of cities, but the state ultimately reasserted authority through arrests, repression, and information control.

• These precedents illustrate a recurring pattern in Cuban politics, where severe economic distress does not automatically translate into regime change as long as the ruling coalition remains intact.

Yes, but. The difference today lies in the convergence of pressures that rarely appear simultaneously. Cuba faces not only internal economic collapse and renewed protests but also an unusually unfavorable international environment. Venezuela, once the island’s principal energy lifeline, can no longer sustain the relationship it once did. Mexico has reduced its support. Meanwhile, the United States appears more willing than at any point in recent decades to explore political outcomes that could fundamentally alter the Cuban system.

• The presence of a secretary of state personally invested in that objective adds another layer to the equation.

• None of these factors guarantees the fall of the regime, and the Cuban state still retains powerful instruments of control through its military, intelligence services, and Communist Party structure.

• Yet the alignment of these pressures makes the current moment distinctive.

The bottom line. Cuba has faced vulnerability before and has repeatedly demonstrated the resilience of its political system. What makes the present situation different is the simultaneous collision of economic breakdown, social unrest, diplomatic engagement, and external pressure. A regime that has long relied on external partners to cushion crises now finds itself increasingly isolated, while the United States is signaling a willingness to shape the island’s political future rather than simply contain it.

• Whether this moment ultimately produces reform, transition, or another cycle of survival remains uncertain.

• What is clear is that the Cuban government is confronting one of the most complex strategic challenges of its existence—one that combines internal strain and external pressure in a way the system has rarely faced before.

The Strait of Hormuz has always been one of the world’s most important geopolitical chokepoints. Today, however, it has become something far more consequential: the center of gravity of the current conflict between the United States, Israel, and Iran.

In perspective. As shown in the graphic, the closure—or even partial disruption—of this narrow maritime corridor does not primarily hurt the United States or Europe. Instead, it places enormous pressure on Asia, and above all on China. In other words, the most powerful weapon Iran still possesses may end up harming Beijing more than Washington. The strait normally carries roughly a fifth of the world’s traded oil.

• When Iran began mining the waterway and threatening shipping in retaliation for the U.S.–Israeli strikes that decimated its military infrastructure, global tanker traffic quickly slowed to a crawl.

• Shipping companies halted routes, vessels anchored outside the Gulf waiting for security guarantees, and insurance premiums skyrocketed.

• Iran’s objective is straightforward: if it cannot defeat the United States militarily, it can still disrupt the arteries of the global energy market and impose economic costs on everyone involved.

Why it matters. Yet the distribution of those costs is highly uneven. As the data in the graphic illustrates, China alone accounts for roughly 38% of the crude oil passing through the Strait of Hormuz. India follows with around 15%, South Korea with 12%, and Japan with 11%. Europe, by contrast, receives only a small fraction of its energy through this corridor, while the United States imports virtually none of its oil from the Gulf today. In practical terms, this means the main economic victims of a prolonged Hormuz disruption would be Asian industrial economies rather than Western powers.

• This imbalance places Beijing in a particularly uncomfortable position. China has spent the past two decades deepening its economic footprint in the Middle East, cultivating relations with Iran and the Gulf monarchies alike while positioning itself as a neutral commercial partner.

• But the current crisis exposes a structural vulnerability in that strategy: China depends heavily on the stability of maritime routes that it does not control.

• If Hormuz remains partially blocked tankers continue to be targeted by the IRGC, China’s energy security—and by extension its industrial output—faces immediate pressure.

Between the lines. At the same time, Beijing is unlikely to intervene militarily to secure the strait. Such an action would risk direct confrontation with the United States Navy in a region where American forces maintain overwhelming superiority. For now, China appears confined to diplomatic gestures and rhetorical support for de-escalation while quietly absorbing the economic consequences of the disruption. In strategic terms, Iran’s attempt to retaliate against Washington may therefore end up squeezing its most powerful partner. Meanwhile, oil prices skyrocket and lines accumulate in Chinese gas stations.

• For the United States, the immediate objective is to reopen the strait while dismantling Iran’s ability to threaten it again.

• American naval forces have already destroyed multiple Iranian vessels involved in mining operations and struck key maritime infrastructure tied to Iran’s oil exports.

• The logic behind these operations is consistent with the broader strategy that has defined the conflict so far—neutralize Iran’s capabilities quickly and decisively while avoiding a prolonged ground war.

The bottom line. Iran, meanwhile, is left with increasingly limited options. Its conventional military infrastructure has suffered extensive damage, its air defenses have proven ineffective against U.S. and Israeli operations, and its retaliatory strikes have become less frequent with each passing day. The maritime disruption in Hormuz remains its last meaningful lever of escalation. Whether that lever can be sustained is another question.

• Clearing naval mines and restoring full commercial traffic could take weeks, but the broader balance of power in the Gulf remains overwhelmingly tilted toward the United States and its allies. If Iran’s remaining naval assets continue to be degraded, its ability to keep the strait effectively closed will steadily erode.

• The irony of the crisis is therefore difficult to ignore. Iran’s most disruptive retaliation strategy targets the global energy system, yet the countries most exposed to that disruption are not those leading the military campaign against it.

• Instead, the pressure falls primarily on the Asian economies—above all China—that depend most heavily on the oil flowing through the Strait of Hormuz. In that sense, the battle for this narrow stretch of water may be as much about the future balance of power in Asia as it is about the war unfolding in the Middle East.

The recent legislative elections in Colombia have fundamentally restructured the power incentives within Congress, unfolding amid a volatile backdrop of localized violence and persistent corruption.

The Right-Wing Realignment. This new political map suggests that the road to 2026 will be defined by the ability of traditional movements to reinvent themselves against rising populist tides and a robust left-wing candidate, Iván Cepeda. Understanding these shifts is critical to anticipating the legislative stability of the next administration, especially given Colombia’s role in regional security. The landslide victory of Paloma Valencia in the center-right primary serves as both a restoration and a strategic recalibration for the traditional opposition.

• Valencia, widely regarded as the ideological heir to Uribismo, has effectively marginalized the more radical, Bukele-style approach championed by candidates like Abelardo De la Espriella. Her high vote count is a clear omen for De la Espriella’s prospects. His populist rhetoric, modeled after El Salvador’s hardline security tactics, has seemingly hit a ceiling against Valencia’s established political machinery and institutional backing.

• The strategic selection of Juan Daniel Oviedo as a vice-presidential running mate represents a calculated move toward the center. By pairing her staunch, security-focused project with Oviedo’s more moderate and technocratic profile, Valencia is actively courting centrist—and even some left-leaning—urban voters who are disillusioned with current governance but remain wary of a return to old-school hardline conservatism.

• This security-plus-management ticket aims to bridge the gap between rural security concerns and urban technical demands, potentially tightening the race against a left wing that did not expect Oviedo’s selection as a running mate.

The Leftist Hegemony. A relatively sluggish vote count in the recent legislative contests for left-wing candidates has nonetheless defined the Pacto Histórico’s power as a unified force in the Colombian Congress. Iván Cepeda has emerged as the left’s primary anchor, leveraging his long-standing profile as the chief antagonist of former President Álvaro Uribe and a champion of working-class discourse to maintain a high floor of support. His ability to mobilize the base remains the left’s greatest asset, even as the broader electorate shows signs of voter fatigue with the incumbent administration’s reformist agenda.

• The consolidation of the Pacto Histórico as a disciplined majority party provides a tactical advantage that the fragmented right currently lacks.

• While the right holds more seats in aggregate across various parties, the left’s ability to vote as a single, disciplined bloc may allow it to set the legislative agenda and force the opposition into a reactive stance.

• However, the emergence of the Valencia–Oviedo ticket introduces a new variable that could erode this advantage. If the right can successfully signal consensus around a quid pro quo administration, the left may find its antagonist narrative less effective, forcing Cepeda and his allies to move beyond ideological contrast toward more concrete, performance-based arguments.

The Legislative Maze. The new Congress is defined by a numerical right-wing majority that is too fragmented to lead and a consolidated left-wing minority. Incentives for individual congressmen are increasingly tied to decentralized financing and regional security projects rather than national party platforms. To pass any meaningful legislation, the next administration will need to broker these specific regional interests, effectively turning the legislative process into a series of high-stakes transactions that could slow structural reforms.

• This fragmentation of the right-wing caucuses creates a veto-player environment in which smaller parties—such as the Liberals—hold outsized power as kingmakers.

• Unless the right can agglutinate its votes under a single leadership, the Pacto Histórico will continue to dominate the narrative by simply remaining the only group capable of delivering a reliable bloc of votes.

• The effectiveness of the Pacto Histórico’s consolidated majority will ultimately depend on internal discipline. If the coalition fractures under the weight of presidential ambitions or regional disputes, the legislative branch will likely descend into a period of inertia in which neither side can advance its project.

In conclusion. Colombia is entering an era of transactional politics in which the ability to build bridges may prove more valuable than the ability to build walls. Paloma Valencia’s moderate pivot suggests that the right has learned the lessons of the previous cycle, yet the fragmentation of the legislature remains a formidable obstacle for any future president.

• The primary risk ahead is not a victory for one side or the other, but legislative paralysis that leaves critical security and economic issues unaddressed while political elites remain locked in stalemate.