Donald Trump returned to office promising to treat the Western Hemisphere as America’s business again, and he has spent eighteen months proving he meant it. On his first day back he ordered Latin American criminal syndicates designated as Foreign Terrorist Organizations, a status that by February 2025 covered the Sinaloa Cartel, the Jalisco New Generation Cartel, and Tren de Aragua. A classified directive in August 2025 authorized Pentagon operations against those groups.
Beginning September 2, 2025, American forces started blowing up boats, killing 221 people by mid-July. Then, on January 3, 2026, Delta Force operators lifted Nicolás Maduro out of Miraflores Palace and flew him toward a Manhattan courtroom. “We’re there now, and we’re going to stay until such time as the proper transition can take place,” Trump said.
Washington has announced that regimes here are contestable and that force settles the question. Other people hear that too. Men with rifles, investors with appetites, and consultants with slide decks have always read a permissive Washington as an invitation, and America has a long-forgotten tradition of citizens who accepted taking military action without waiting for orders from DC.
They were called filibusters, from the Spanish filibustero, borrowed in turn from the Dutch word for freebooter. The practice began in the 1790s, when Americans plotted private assaults on Spanish possessions to the south and British Canada to the north. Congress answered with the Neutrality Act of 1794 and a tougher version in 1818, making it a federal crime to launch a military expedition from American soil against a nation at peace with the United States. Americans flouted both for seventy years.
Francisco de Miranda showed how it worked. The Venezuelan revolutionary raised American money in New York, leased an armed vessel called the Leander, recruited roughly two hundred volunteers, and sailed on February 2, 1806 to liberate his homeland. He seized La Vela de Coro and raised a tricolor that Venezuela flies to this day, but no one joined him and Spanish reinforcements pushed him back to sea within a fortnight. His American financiers faced Neutrality Act prosecution and mostly walked.
Former Vice President Aaron Burr tried something grander, moving men down the Mississippi toward Spanish Mexico to carve out his own dominion, until General James Wilkinson betrayed him. Supreme Court Chief Justice John Marshall’s insistence that treason requires an overt act of war produced an acquittal in 1807.
The model matured into an industry. Narciso López, bankrolled by Southern planters who wanted Cuba admitted as a slave state, mounted three invasions from New Orleans between 1848 and 1851 and died by garrote in Havana during the last expedition. William Walker, a Tennessee lawyer and newspaperman, sailed from San Francisco in October 1853, took La Paz, proclaimed a Republic of Lower California, then surrendered in San Diego, where a sympathetic jury acquitted him in eight minutes.
However, this did not prevent Walker from getting back into the filibustering game. In June 1855, Walker entered Nicaragua’s civil war with fifty-eight men at a faction’s invitation, captured Granada that October, declared himself president in 1856, and legalized slavery to court Southern capital. He then revoked Cornelius Vanderbilt’s transit concession, and the shipping magnate financed a coalition of Costa Rica, Honduras, El Salvador and Guatemala that broke him. Walker surrendered in May 1857, tried twice more, and faced a Honduran firing squad on September 12, 1860. Historians credit that war with hastening the formation of a Latin American identity defined against the United States’ overreach in the region.
The twentieth century nationalized the practice. The CIA armed Guatemalan exiles under Carlos Castillo Armas to topple Jacobo Árbenz in 1954 after he expropriated United Fruit Company land, pairing a small force with fake radio broadcasts and real bombing runs. Seven years later, roughly 1,400 Cuban exiles of Brigade 2506 landed at the Bay of Pigs and collapsed in three days when the promised air cover never came from the United States. President Ronald Reagan’s efforts to arm the Contras in Nicaragua, funded partly through schemes exposed in Iran Contra, carried the logic into the 1980s.
Freelancers never disappeared. In April 2009, Bolivian police stormed a Santa Cruz hotel and killed Eduardo Rózsa Flores and two European associates, alleging a plot against Evo Morales. In May 2020, former Green Beret Jordan Goudreau and his firm Silvercorp USA sent boats toward Venezuela carrying roughly sixty Venezuelan defectors and two American veterans, hoping to seize then-President Nicolás Maduro. Both craft were intercepted and the Americans were paraded on state television. Goudreau, indicted in 2024 on arms export charges, skipped his bond hearing in October 2025 and remains a fugitive.
The Haitian case should sober everyone. Twenty-eight mercenaries, twenty-six of them former Colombian soldiers, killed President Jovenel Moïse on July 7, 2021, after Miami-based CTU Security recruited them. On May 8, 2026, a federal jury convicted Arcangel Pretel Ortiz, Antonio Intriago, Walter Veintemilla and James Solages, and among the counts was expedition against a friendly nation, the direct descendant of the statute written for Miranda and Walker. “Using U.S. soil as a staging ground for a violent plot overseas is a grave violation of our laws and, more fundamentally, our sovereignty,” said Assistant Attorney General John Eisenberg. Prosecutors described a scheme to install a handpicked president and harvest the resulting contracts.
Erik Prince fits this lineage. Reuters reported in April 2019 that the Blackwater founder had spent months pitching investors and Trump allies on fielding 4,000 to 5,000 fighters drawn from Colombia and elsewhere to remove Maduro for Juan Guaidó, at a cost near $40 million. Prince argued Venezuela needed what he called a “dynamic event” to break the stalemate. The White House declined. Prince has since stopped needing permission. In March 2025, President Daniel Noboa announced that Ecuador had “established a strategic alliance to strengthen our capabilities in the fight against narcoterrorism and the protection of our waters from illegal fishing.” Retired Army commander Luis Altamirano called it “deplorable” that Ecuadorean officials “seek to hire the services of a mercenary army.”
In Haiti, the arrangement went further still. Prince’s Vectus Global has run drone operations there since March 2025 under a reported ten-year arrangement covering customs and tax collection. Human Rights Watch estimates 1,243 people killed across 141 drone operations between March 2025 and January 2026, including forty-three civilians and seventeen children. On July 21, Reuters reported that American officials told Congress they intend to formalize coordination with the firm. “This is a war situation, and unfortunately, that’s a reality for the situation we find ourselves in,” Colonel Justin Gorkowski testified. Rep. Joaquin Castro (D-TX) objected to Prince’s scheme, noting that “Private military contractors like Vectus Global are putting innocent Haitians at risk.” Prince has separately urged strikes inside Mexico.
Every precondition for a filibustering revival is assembled. Terror designations supply a legal vocabulary for private violence. Two decades of war produced a labor pool of unemployed operators. Weak governments from Port au Prince to Quito are openly shopping for armed help. A sitting president has demonstrated that seizing a head of state is a viable policy. Somewhere right now, an American with a boat, a roster and a pitch deck is running the same arithmetic William Walker ran.
Given this administration’s appetite for hemispheric adventure, the question is not whether such a man exists but whether anyone in the White House will discourage him.
