US President Donald Trump has increasingly relied on naval blockades to exert pressure on Venezuela, Cuba, and Iran, but experts caution that applying this strategy in the Middle East involves distinct and complex challenges. Unlike the Caribbean nations, Iran controls the strategic Strait of Hormuz, a key passage through which about 20% of the world's oil shipments pass. This control gives Tehran significant leverage, especially as prolonged disruptions risk global economic consequences, including steep rises in energy prices that may complicate US political dynamics ahead of the November elections.

Recent confrontations have underscored the heightened tensions in the Strait of Hormuz. The US military reported seizing another tanker linked to illicit Iranian oil smuggling on Thursday, following Iran’s Revolutionary Guards capturing two vessels in the same vital waterway the day before. President Trump further escalated the situation by ordering US forces to “shoot and kill” Iranian small boats suspected of laying sea mines in the strait.

However, analysts emphasize that the blockade on Iran differs markedly from US measures against Venezuela and Cuba. In Venezuela’s case, much of the US’s leverage appeared tied to a military operation that captured President Nicolás Maduro and the subsequent cooperation of his vice president, Delcy Rodríguez, now acting president. Meanwhile, the longstanding US embargo on Cuba has inflicted severe economic hardship but has failed to achieve its goal of regime change.

Todd Huntley, director of Georgetown University’s National Security Law Program and a retired Navy captain, stresses significant geopolitical and military distinctions between Iran and America’s Western Hemisphere adversaries. While Iran’s economy has suffered from the blockade, it continues to circumvent some restrictions and export sanctioned oil, according to shipping data from maritime intelligence firms.

There are reports of "shadow fleet" traffic keeping Iranian oil moving through methods such as spoofing ship tracking systems or navigating near Pakistani waters to avoid US interception. Maritime historian Salvatore Mercogliano notes the volume of shipping traffic complicates enforcement and that blockades are typically one component of broader conflict strategies rather than standalone solutions.

US Central Command head Adm. Brad Cooper claimed last week that no ship had evaded US forces and that 31 vessels were turned back as of midweek. Yet independent maritime analysts remain skeptical, citing ongoing, covert Iranian shipments through the Gulf of Oman and Persian Gulf.

Historically, naval blockades like those in World War I have had long-term effects but require sustained patience and control to succeed. Max Boot, a military historian at the Council on Foreign Relations, suggests President Trump’s expectation of quick results may be misplaced. Boot contends that Trump’s perceived success in Venezuela, driven largely by unique political events rather than solely naval pressure, may have shaped an overly optimistic view of blockades as a tool against Iran.

Ultimately, experts agree that Iran’s strategic position and military capabilities make the US blockade’s outcome uncertain. The ongoing situtation highlights a contest of endurance, with both Washington and Tehran weighing the economic and political costs as regional tensions persist.