Will Iran Be Afghanistan 2.0?

Dear all,

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

While the war in Iran has demonstrated clear military superiority and success by the U.S. and Israel, as the days go by, the ghosts of Afghanistan and Iraq begin to reemerge. The idea of completely collapsing the Iranian regime through airpower alone, without an internal resistance rising, is far from realistic. That uprising, however, could risk balkanization, which would require boots on the ground—that cursed expression no U.S. president wants to be associated with.

The risk is high, and with midterms around the corner, Trump is faced with the need to resolve this quickly. Once the U.S. got involved, it simply cannot leave things in Israel’s hands and bail out. That would be another nail in the coffin for the GOP in the midterms. Time is running out, and support for the war effort is declining, especially among independents—the key to any election in a polarized America.

While all of this is unfolding, Russia is taking advantage of high oil prices and the diversion of U.S. resources to the Middle East to use its traditional tool to pressure America: Cuba. While the Cuban regime is close to collapse, its traditional safeguard appears to be stepping in once again. This time, however, it is weaker and in crisis—but present nonetheless. Geopolitics are becoming increasingly complex, both in the Caribbean and abroad, complicating the chessboard Trump had been dominating so decisively so far.

In this issue, you will find:

• Iran After the War: Balkanization, Boots on the Ground and Proxies

• Trump Is Winning in Iran, Losing at Home

• Asymmetric Reciprocity: Moscow Is Turning Havana into a Second Front

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The war in Iran has been, so far, a military success, but the phantom of Afghanistan and Iraq flies above the minds of strategists and military leadership.

In perspective. The military phase of the war in Iran has been defined by speed, precision, and overwhelming asymmetry. The United States and Israel have relied on sustained air campaigns to dismantle critical components of the Iranian regime without deploying large numbers of ground troops. If that phase succeeds—if the regime’s command structure is sufficiently degraded and its capacity to project force collapses—the central question immediately becomes what follows.

• History suggests that removing a regime is often the least complex part of the process. What replaces it is where conflicts are won or lost.

• In Iran’s case, the range of possible outcomes is unusually wide, and each carries significant risks not only for the country itself but for the broader regional order.

How it could work. One of the most discussed scenarios is the return of Reza Pahlavi, the son of the last Shah. From a symbolic perspective, he offers something no other figure currently does: a recognizable national identity that predates the Islamic Republic and connects with Iran’s longer historical narrative as Persia. Pahlavi has positioned himself as a liberal figure advocating for a secular, parliamentary monarchy in which the monarch would not govern but serve as a unifying institution.

• His proposal includes a national referendum to allow Iranians to choose their preferred political system.

• While polling is scarce, some attempts have shown great support for this. A 26% of Iranians want a secular republic, 21% want the return of the monarchy and a 33%—that keeps narrowing— is undecided. However, around an 80% of the population opposes the continuation of the Islamic Republic.

• In a context where a large majority of the population appears to favor a departure from the current regime, this platform has gained traction, particularly among younger generations and segments of the diaspora.

Yes, but. However, the viability of a Pahlavi-led transition depends less on popular sentiment than on elite dynamics within Iran. The country’s political system is not an empty shell waiting to be filled; it is a dense network of institutions, patronage systems, and armed actors. The most important of these is the Islamic Revolutionary Guard Corps (IRGC), which functions not only as a military force but as an economic and political power center.

• Even if the upper clerical leadership has been severely weakened, the IRGC retains the capacity to organize resistance, as it has proven in the Strait of Hormuz.

• A transition led by Pahlavi would therefore almost certainly face opposition from elements of the existing power structure that have both resources and incentives to resist change.

Why it matters. This raises the possibility of internal conflict. One plausible fault line runs between the IRGC and the conventional military. While the IRGC is ideologically tied to the Islamic Republic, the regular army has historically been more nationalist and less directly invested in the regime’s ideological project.

• In a post-war environment where central authority is weakened, these two institutions could diverge in their loyalties.

• A scenario in which segments of the army align with a transitional authority while the IRGC attempts to preserve remnants of the old system is not difficult to imagine.

• Such a split would transform a regime collapse into a fragmented internal struggle, complicating any effort to establish a coherent post-war government.

Hidden in plain sight. Beyond the internal power struggle, Iran’s is home to multiple minority groups with distinct identities and, in some cases, longstanding grievances. Among these, the Kurdish population in western Iran represents one of the most consequential variables. Kurdish armed groups have experience operating in mountainous terrain and have previously collaborated with external actors. In a scenario where the central government weakens significantly, Kurdish forces could attempt to expand their autonomy or even push toward the creation of a separate political entity. Such a development would not occur in isolation.

• Turkey has consistently opposed the emergence of Kurdish statehood in the region and has demonstrated a willingness to intervene militarily to prevent it.

• An Iranian collapse that opens space for Kurdish advances could therefore trigger Turkish involvement, expanding the conflict beyond Iran’s borders. At the same time, other regions—such as areas with significant Azeri or Baluchi populations—could experience their own forms of fragmentation.

• The result would be a risk of de facto Balkanization in a country of more than ninety million people, located at the intersection of multiple strategic regions.

Between the lines. These dynamics point toward a broader concern: the possibility that Iran could follow a trajectory similar to Iraq after 2003 or Libya after the fall of Gaddafi, but on a much larger scale. In those cases, the removal of centralized authority created power vacuums that were filled by competing militias, regional actors, and fragmented political structures. Iran’s size, population, and strategic importance would amplify those risks considerably. The presence of sensitive materials and infrastructure—including its nuclear program—adds another layer of urgency to the question of post-regime stability.

• In this context, the assumption that the United States can achieve its objectives through airpower alone becomes increasingly difficult to sustain.

• A strategy focused exclusively on degrading the regime’s capabilities without addressing the post-war order risks creating a vacuum that external and internal actors will rush to fill. Deploying U.S. and allied forces to stabilize the country during a transition carries its own set of risks, including the possibility of becoming entangled in a prolonged and costly occupation.

• The dilemma is not between a clean intervention and a clean exit; it is between different forms of another forever war, which Trump vowed never to do again.

The bottom line. The scenario in which a Pahlavi-led transition emerges as the central organizing framework remains one of the more plausible outcomes, particularly if elements of the Iranian elite conclude that a controlled shift is preferable to uncontrolled collapse. Yet even this pathway would not unfold without resistance. The institutions that sustained the Islamic Republic for decades are unlikely to disappear quietly—and hardly achievable only through airstrikes—and any attempt to replace them will have to contend with actors that retain both coercive power and entrenched interests.

• The removal of the current regime, if it occurs, will open a phase of profound uncertainty in which the risk of fragmentation, conflict, and external intervention remains high.

• For the United States, the central question is whether it is prepared to manage that phase or whether it assumes that the end of the war will also mark the end of its involvement.

• History and an analysis of the complex Iranian reality suggests that such an assumption would be difficult to sustain.

While the military campaign in Iran may be delivering results abroad, it is already generating political costs at home—and those costs are moving in the wrong direction for the White House.

In perspective. At the aggregate level, public opinion is deteriorating. Among U.S. adults, disapproval of Trump’s handling of the situation rises from 52% to 56% in just one week, while approval drops from 39% to 36%. That shift is not dramatic, but it is meaningful given how early the conflict still is, and how fast it is falling.

• Wars tend to follow a predictable political curve of an initial rally effect, followed by erosion as uncertainty, costs, and duration increase.

• This data suggests the U.S. may already be moving past that initial phase.

Between the lines. The partisan breakdown is even more revealing. Republican support remains overwhelmingly strong, with approval holding above 80% and disapproval in the low teens. That indicates Trump has not lost his base, which is critical for short-term political stability. However, that is not where elections are decided. The movement that matters is happening among independents, where approval drops from 30% to 24% and disapproval jumps from 53% to 63%.

• That is a ten-point swing in disapproval in a single week—exactly the kind of shift that determines midterm outcomes.

• Democrats, meanwhile, are effectively locked in opposition, with disapproval holding at 92% across both periods. There is no room for deterioration there, but that also means the president has no ability to expand support across the aisle.

• The political battlefield is therefore narrowed almost entirely to independents, and the trend line is clearly negative.

Why it matters. What this suggests is that the political viability of the war depends heavily on timing and outcome. As long as the conflict remains limited, successful, and clearly defined, the administration can contain the domestic fallout. But if the war drags on, becomes more complex, or introduces new risks—such as energy shocks, market instability, or the possibility of U.S. troop involvement—the erosion among independents is likely to accelerate.

• This is where the strategic and political dimensions begin to converge. The current military approach—high-intensity air campaigns without boots on the ground—has been effective precisely because it minimizes visible costs.

• It allows the administration to project strength without triggering the domestic backlash historically associated with prolonged wars. However, that balance is fragile.

• The moment the conflict shifts from rapid degradation of Iranian capabilities to managing the aftermath—whether through stabilization efforts, proxy conflicts, or extended deterrence—the political calculus changes.

The bottom line. The key risk for the administration is not only immediate backlash, but most importantly, cumulative fatigue. Voters are not yet reacting to casualties or economic disruption at scale, but they are signaling discomfort with the direction of the conflict. If that perception hardens, the war could become a liability heading into the midterms, particularly in competitive districts where independent voters decide outcomes.

• In that sense, the data points to a narrow window. A quick, decisive outcome that allows the United States to disengage would likely stabilize public opinion and preserve political capital.

• Anything slower or more ambiguous risks turning a foreign policy success into a domestic political burden. Overall, when the midterms come, it will be the economy, stupid.

The geopolitical significance of Cuba has undergone a radical transformation, shifting from a historical focal point of American hemispheric security to a cornerstone of Russia’s modern strategy for a multipolar world.

In perspective. While the island’s proximity to Florida once defined the limits of the Monroe Doctrine, it now serves as a primary site for asymmetric reciprocity in response to Western maneuvers in Eurasia. Moscow’s strategy has leveraged historical tensions, military agreements, and global energy fluctuations to establish a permanent strategic foothold 90 miles from the United States. From a geographical security standpoint, Cuba has always been a pivot point for American hegemony in geopolitical doctrine, especially from the perspective of the Founding Fathers.

• Cuba was viewed through a lens of geographic security and was considered a critical pivot point for establishing American hegemony in the Western Hemisphere. This obsession was rooted in the island’s role as a vital link in trade routes, specifically its connection to the Mississippi River, which made it indispensable for the economic stability of the early United States.

• Early American leaders were perpetually preoccupied with the threat of a global hegemon like Great Britain gaining control over Cuba, fearing that the British Navy would use the island to launch hostilities against the young republic. To mitigate this risk, the U.S. strategically preferred that Cuba remain under the control of a decadent and weakening Spanish Empire rather than fall into the hands of a competing great power.

• This historical backdrop of geographic isolation as a security buffer for the U.S. is precisely what contemporary Russian doctrine seeks to dismantle by exploiting Cuba’s location.

The Russian view. The geopolitical doctrine on Cuba frames the state as a necessary asset to destabilize U.S. security. Moscow doctrinally categorizes Cuba as a state that serves to validate the Kremlin’s broader vision of a multipolar global order in which U.S. influence is no longer absolute. Within this framework, Cuba is treated as a priority partner whose political and economic survival is seen as a direct litmus test for Russia’s own global credibility.

• The Kremlin believes that maintaining a sovereign bastion just 90 miles from Florida proves that American hegemony is regionally bounded and that alternative powers like Russia and China can project security into the U.S. near-abroad.

• This presence is codified under the 2025 Military Cooperation Agreement, which formalizes Cuba as a site for asymmetric reciprocity against Western escalations in Eurasia—such as missile transfers to Ukraine.

• Beyond military ties, Russia views the island as a critical testing ground for its doctrine of technological and financial sovereignty in a global environment increasingly dominated by Western sanctions.

Power projection. Moscow uses Cuba as a direct counterweight to NATO’s presence on Russia’s borders, where expansions on one side create a vicious cycle of power for both the U.S. and Russia. Under the framework of the 2025 Military Cooperation Agreement, Russia has established the legal grounds to deploy technical-military units directly onto Cuban soil. This has manifested in strategic signaling, with Russian officials floating the potential deployment of the Oreshnik hypersonic missile system to the island as a symmetrical response to U.S. military aid to Ukraine.

• The Russian naval presence has intensified through the 2024–2026 deployments of Yasen-class submarines, forcing Washington to divert significant naval and intelligence resources to monitor its own strategic perimeter.

• This tactic effectively creates a second front in the Caribbean, diluting the focus of the United States and NATO on Eastern Europe by presenting a direct threat to the American mainland.

• In response to the 2026 U.S. energy blockade, Russia has utilized its shadow fleet to maintain a vital fuel bridge to Havana. The intent of this operation is to demonstrate that Russia is a reliable power capable of challenging U.S. maritime dominance and shielding its partners from Western pressure.

Between the lines. Macroeconomic effects of the Middle East conflict have created a window of opportunity for Russia and its influence on the island. The outbreak of the U.S.–Israeli war with Iran caused Brent crude prices to surge into the USD 100–120 range, providing the Russian budget with the liquidity needed to fund high-risk operations. This financial windfall has allowed the Kremlin to subsidize Cuba’s energy needs during blockades, converting excess oil profits into a permanent strategic foothold in the Caribbean.

• Russia views the conflict in the Middle East as a kinetic shield, in which Iran absorbs U.S. military resources while Moscow acts as a geopolitical opportunist, using high fuel prices to finance its own global expansion.

• The resulting Western distraction and focus on the Strait of Hormuz have allowed Russia to simultaneously intensify pressure on Ukraine while opening a Caribbean front.

• The standoff in the Caribbean is defined by gray zone operations, in which Russia exploits Cuba’s proximity to deploy power levers such as signal intelligence and hypersonic threats. This asymmetry forces Washington into a security dilemma, requiring a choice between committing resources to a containment effort or accepting a Russian presence that reduces the advantage of U.S. geographic isolation.

In conclusion. The resurgence of Cuba as a Russian strategic asset represents a calculated attempt to dismantle the traditional security architecture of the Western Hemisphere. By leveraging high oil prices and diversionary conflicts in the Middle East, Moscow is attempting to transform a regional partner into a forward-deployed second front.

• This evolution could force the United States to confront a sustained Russian military and financial presence 90 miles from its coast, effectively diluting American geographic invulnerability.

• Real power, however, stands as the main breaking point. Russia’s gamble is brilliant, but the decadent situation on the island and the diplomatic backchannels that the U.S. is implementing to choke the regime might make Russia’s efforts useless.