Trump wants Venezuela’s oil. History says tread carefully.

For more than two centuries, U.S. efforts to control the riches in sugar, bananas, rubber, and oil to be found in South and Central America and the Caribbean have met with mixed results.

The difficult topography, a local aversion to so-called “gunboat" diplomacy, and corrupt political regimes have been among foreign firms’ many obstacles. While some companies made fortunes, others beat hasty retreats.

Now, Trump is vowing to “run" Venezuela to unlock its oil reserves, the world’s largest. But before he and American oil majors rush back in, they’d do well to look at past U.S. exploits in the region. History shows, if anything, that imperialist ventures in Latin America don’t always pay off.

Already, many global leaders have expressed alarm at the U.S.’s seizure of Venezuela’s president, Nicolás Maduro, earlier this month—and at Trump’s threats directed at Cuba, Colombia, and other governments in the region.

U.S. corporations are taking a cautious approach to Trump’s call for investment in Venezuela.

“We’ve had our assets seized there twice," Exxon CEO Darren Woods said after meeting with oil executives on Jan. 9. “You can imagine to re-enter a third time would require some pretty significant changes from what we’ve historically seen here and what is currently the state."

Chevron is the only major U.S. oil company presently active in Venezuela. Exxon, which declined to comment for this article, ultimately sued Venezuela for $12 billion but saw only a fraction of that.

U.S. relations with Latin America haven’t always been this strained.

Founding Father Alexander Hamilton met a kindred spirit in Caracas-born Francisco de Miranda, who fought for both the American and French revolutionary causes.

Miranda wanted to lead a Latin American revolution, and create from Spain’s former colonies a grand republic of Colombia stretching from Cape Horn to California. But he needed muscle.

Hamilton, eyeing the region’s natural resources to support his vision of an industrialized U.S., proposed backing Miranda with American troops and a British fleet.

“The command in this case would very naturally fall upon me," Hamilton wrote in 1798.

The invasion never materialized. But Hamilton’s belief that the Western Hemisphere should be closed to European meddling was memorialized in 1823’s Monroe Doctrine.

As for Miranda, he died in a Spanish prison, his dream of a united Latin American republic dying with him.

Instead, after the region won independence from Spain in the early 19th century, it splintered into almost three dozen states of varying commitment to democracy and the rule of law.

Many countries fell under the domination of caudillos, or strongmen whose power stemmed from financial control of the land’s resources. American writer O. Henry, hiding in Honduras to avoid embezzlement charges back home, coined the term for such places: “banana republic."

By 1854, Cuba was one of Spain’s few remaining New World colonies, and Southern expansionists coveted it—and its lucrative sugar plantations—as a new U.S. slave state.

Three American diplomats, including future President James Buchanan, hatched a plan to offer Spain an ultimatum: Sell Cuba for $120 million, or prepare for war. They premised their secret proposal, the Ostend Manifesto, on national defense.

“[T]he Union can never enjoy repose, nor possess reliable security as long as Cuba is not embraced within its boundaries," they wrote.

When the plot went public, it was denounced outside Dixie — Horace Greeley’s New-York Tribune called it the “Manifesto of the Brigands"—and the idea was shelved as America slid toward civil war.

The U.S. wouldn’t take control of Cuba until 1898 and the Spanish-American War—Remember the Maine!—when the U.S. also claimed Puerto Rico, the Philippines, and more.

Lt. Col. Theodore Roosevelt, “holding his sword and shouting for his men to follow him," helped win the day at San Juan Hill, Cuba, a decisive battle in the war.

A few years later, as president, the old Rough Rider called for his country to follow him—this time to Panama.

Roosevelt was intrigued by the military and commercial possibilities of a canal across the isthmus, cutting 8,000 miles off a New York-San Francisco voyage.

No matter that Panama was a state within the Republic of Colombia. In 1903, Roosevelt approved a coup by local insurgents, and sent in the gunboats.

“[A] vulgar and mercenary venture," the New York Evening Post called it.

Colombia backed down and Roosevelt got his canal, completed in 1914. Jimmy Carter returned it 63 years later, but Trump wants it back.

But the interventions weren’t limited to government leaders. American fruit mogul Samuel Zemurray, known as “Sam the Banana Man," sent his own gunboat, the decommissioned USS Hornet, into action when he didn’t like the tax policies in Honduras — O. Henry’s original Banana Republic.

“Bonilla Gone With Hornet," the New York Times reported Dec. 24, 1910, after the gunboat left New Orleans carrying Honduras’s ex-president Manuel Bonilla, American mercenaries, arms, and ammunition.

After two years of war, Bonilla was back in Honduras’s presidential palace, and “Sam the Banana Man" got his tax break.

Industrialist Henry Ford was after rubber when he built the company town Fordlandia on a Connecticut-sized patch of Brazil’s Amazon forest in 1927.

Ford Motor’s global empire already included mines, forests, and steel mills. A rubber plantation was the next step in the founder’s goal of total in-house production. “Civilizing" the Amazon, as Ford perceived it, was a side benefit.

As it happened, Fordlandia was beset by smallpox and yellow fever, rubber-destroying fungi, and labor unrest that required military intervention. Little rubber was produced.

In 1945, having lost $15 million, Ford sold Fordlandia back to Brazil for $250,000—“a virtual gift," the Springfield, Mass., Daily Republican called it.

During that span, Ford’s cars had helped create booming demand for oil, threatening to outstrip U.S. production. Soon help came from farther afield.

After the discovery of a major oil gusher near Venezuela’s Lake Maracaibo, the race was on for U.S. oil producers, the Los Angeles Times reported in its Feb. 6, 1922, article, “Flock to Venezuela Oil Field."

By 1924, Standard Oil of New Jersey, predecessor to Exxon Mobil, was one of 26 oil companies that had joined the flock to Caracas. There, dictator Gen. Juan Vicente Gómez demanded hefty kickbacks for the right to drill.

Pay and drill they did, with the country’s production rising to 137 million barrels in 1929 from 1.4 million in 1921. Venezuelan crude powered the allies during World War II, and American investment continued to grow.

Then, in 1976, Venezuela lowered the boom, nationalizing its oil industry.

“Today we are fixing the destiny of the nation," President Carlos Andrés Pérez announced to cheering crowds.

Foreign oil assets were confiscated by state-owned Petróleos de Venezuela SA—the same PdVSA that Trump is trying to fix today.

That was the first time Exxon’s assets were seized. The company returned during Venezuela’s “oil opening" policy of the 1990s, only to be ousted again in 2007, this time by Maduro’s predecessor, longtime President Hugo Chávez.

No wonder Exxon isn’t rushing back. It may be recalling the old proverb: Fool me once, shame on you. Fool me twice, shame on me.

Write to editors@barrons.com