They called the channel Boca del Infierno -- the Mouth of Hell. On a March morning in 1825, the pirate Roberto Cofresi was threading his sloop Anne through this narrow passage between Cayo Caribes and Cayos de Barca, heading into the sheltered waters of Jobos Bay on Puerto Rico's southern coast. He did not know that behind him, an unlikely coalition was closing in: an American warship, two Danish sloops, and a Colombian brigantine, all hunting the same man. The age of Caribbean piracy was gasping its last breath, and Cofresi -- charming, elusive, and increasingly desperate -- was about to become its final casualty.
The hunt for Cofresi had frustrated navies for years. The pirate operated from shifting hideouts along Puerto Rico's coast, preying on French, Danish, Dominican, and American vessels alike. His reach was democratic in its targets and infuriating in its success. By early 1825, both the American and Danish navies had been searching independently without result, and the governor of Puerto Rico recognized what the separate powers would not admit: they needed each other.
Commander John Drake Sloat of the USS Grampus secured permission for two small Danish sloops to join his pursuit. When word reached the captain of a Colombian brigantine named La Invencible, he requested a place in the mission and was granted one. Sloat armed the new arrivals, assigned medic Samuel Biddle and additional officers, and assembled a total force of 23 sailors. At dawn, the combined fleet set course for Caja de Muerto, an island off Ponce where Cofresi was rumored to be hiding. What followed was one of the Caribbean's last genuine pirate chases.
Cofresi was not at Caja de Muerto. He was already moving, navigating Boca del Infierno with the Anne when the allied ships spotted him. The engagement that followed lasted forty-five minutes -- a running battle through shallow, reef-strewn waters where a wrong turn could ground any vessel. Cofresi, already wounded alongside crewmates Juan Carlos Torres and Juan Manuel de Fuentes, ordered his crew to make for Playa de los Rodeos, hoping to abandon ship and disappear into the mangroves and swamps beyond the beach.
The San Jose y las Animas directed cannon fire at the shoreline as the pirates scrambled ashore. One shot struck pirate Juan de Mata, killing him instantly. Two other crew members died in the exchange, and Sloat later estimated that a third of Cofresi's crew had been lost, based on bodies he observed in the water surrounding the grounded sloop. The Anne itself was refloated by Bautista Pierety, its cargo of stolen goods recovered. But the pirate captain had vanished into the swamp.
At Guayama, local troops fanned out across the municipality. The search continued through the day and into the night. According to a later account in the Boston Traveller, Cofresi employed cunning tactics ashore -- stealing a herdsman's clothes and animals, driving the herd toward soldiers to scatter them, and giving false information about his crew's whereabouts while standing unrecognized among his pursuers.
The deception could not last. Near midnight, a man named Juan Candido Garay spotted Cofresi and his remaining crew. Captain Manuel Sanchez and corporal Jose Maria Bernabe completed the arrest. The rest of the crew were captured by police from Patillas and Guayama on March 7 and 8, 1825. Ten days later, a formerly enslaved man named Carlos, the last member of the crew, was arrested while hiding at a hacienda, carrying 2.5 ounces of gold.
At the Guayama jail, doctor Francisco Roso examined Cofresi's wounds and declared he would survive -- long enough for justice. Governor Miguel de la Torre noted that Cofresi and his crew had never denied being pirates, making them guilty by their own admission. When Sloat visited Cofresi in his cell and asked whether he had captured any American vessels, the pirate replied that he would have, had the opportunity arisen. He confessed to seizing a French sloop, a Danish schooner, a Dominican brigantine and schooner, an American schooner, two local vessels, and a small boat from St. Thomas.
The ripples from Cofresi's network spread far beyond his crew. Investigations into his associates continued for more than a decade, reaching across Puerto Rico's west, south, and east coasts. Pedro Alacan, who had once collaborated with authorities against Cofresi, was himself arrested when his vessel was linked to the pirate's operations. Others fled to St. Thomas, Vieques, and as far as Africa. The day before execution, the pirates were confessed by Catholic priests. Cofresi was blindfolded before a large crowd and put to death, closing Puerto Rico's pirate era for good.
The capture of the Anne generated competing narratives almost immediately. Sloat's American report and Colonel Renovales' Spanish account disagreed on key details: who commanded which vessel, who initiated the pursuit, and who deserved credit. The Gaceta de Madrid published Governor de la Torre praising the effort and referencing the "sleepless nights" his government had spent to "exterminate the pirates." Two decades later, a Boston Traveller reporter added colorful details about Cofresi's escape tactics, while historian Francis Bradlee erroneously claimed the pirate was executed by garrote.
Meanwhile, across the Atlantic, Commander David Porter -- the American naval officer whose controversial raid on Fajardo had helped provoke the multinational cooperation -- was found guilty at his own trial, resigned his commission, and defected. The Caribbean's last pirate hunt had entangled nations, embarrassed admirals, and produced a folk hero whose legend in Puerto Rico would long outlast the facts of his capture.
Located at 17.92N, 66.22W on Puerto Rico's southern coast, near Jobos Bay and Guayama. The action took place in the channel between Cayo Caribes and Cayos de Barca (Boca del Infierno), visible from lower altitudes as a narrow passage between small keys leading into Jobos Bay. Nearby airports include Mercedita Airport (TJPS/PSE) in Ponce, approximately 30 nm west, and Luis Munoz Marin International Airport (TJSJ/SJU) in San Juan, approximately 45 nm north. The southern coast of Puerto Rico offers clear views of the reef-fringed shoreline and bay systems where 19th-century pirate vessels operated. Best viewed at 3,000-5,000 ft for coastal detail.