Cold Open

It’s late October 1823, off the coast of Puerto Rico.

32-year-old Roberto Cofresí squints against the early morning sunlight that streams across the deck of the ship. Roberto is a pirate captain, and, today, he’s hoping for another rich prize.

He snaps open his telescope, sweeping it in an arc to the west, but all he sees is the coastline of a nearby island.

He thinks for a moment then hands the telescope to one of his men and sends him up to the crow’s nest for a better look. Roberto has a hunch, a feeling that there’s something out there. And over the years, he’s learned to listen to his gut… it pays off again now. The man in the crow’s nest calls down to the deck excitedly. There’s a sail just beyond the island. It looks like a merchant ship.

Roberto grins—and barks out an order. His men spring into action, turning their vessel on a course to intercept. As the ship picks up speed, Roberto marches to the prow.

Eyes fixed on the horizon, his hand drifts to the trusty cutlass strapped to his side. With any luck, he won’t have to use it. If the merchant sailors know what’s good for them, they won’t put up a fight. But either way, Roberto will be taking their cargo.

The merchant ship doesn’t offer much resistance to Roberto Cofresí and his band of pirates, and the tobacco, tar and US currency notes it was carrying is soon nestled in the bowels of Roberto's ship. This brazen attack is no isolated incident, though. Roberto has a growing reputation as one of the most audacious and dangerous pirates in the Caribbean. But like most pirates, Roberto’s luck will prove fleeting, and he will eventually be captured after a thrilling chase on March 5th, 1825.

Introduction

From Noiser and Airship, I’m Lindsay Graham and this is History Daily.

History is made every day. On this podcast—every day—we tell the true stories of the people and events that shaped our world.

Today is March 5th, 1825: The Hunt for the Last Pirate of the Caribbean.

Act One

It’s 1795, in Cabo Rojo, Puerto Rico, 30 years before the capture of Roberto Cofresí.

Down on the beach, four-year-old Roberto plays in the surf, laughing as the warm Caribbean waters tickle his feet. Watching on with a smile is Roberto’s aunt. His mother died not long ago, so now it's his aunt that's looking after him.

And as he plays in the surf, Roberto spots a clutch of white sails on the horizon, glowing in the afternoon sun. He points to the ships and asks his aunt where those boats are going.

Putting her hand on his shoulder, Roberto’s aunt kneels down beside him and tells him that those ships are carrying sailors to distant lands, their hulls packed with exotic foods and spices, maybe even treasure. It’s an exciting thought for young Roberto, he imagines himself one day sailing over the horizon to adventure on the sea.

His family has ties to European nobility, but they’re not wealthy. Roberto and his four siblings only have a modest inheritance and few prospects. So, as he grows up, Roberto finds work on small fishing boats. It’s not the glamorous life on the waves he heard about as a child, but it’s a living.

Roberto works as a fisherman for four years, until he feels like he knows every inch of Puerto Rico’s coastline. Then, an opportunity presents itself to broaden his horizons. He joins a crew of a merchant ship, transporting goods across the Caribbean. It’s a chance for him to deepen his knowledge of the sea and sailing.

But unfortunately for Roberto, not long after he starts his job, the conflict between Spain and its Latin American colonies escalates. Maritime trade in the Caribbean takes a hit, and Roberto’s new employer begins sailing less and less. Roberto is soon stuck at home in Puerto Rico, with no job—and a family to feed. He grows so desperate for money that he joins a local criminal gang who steal cattle and crops. And during these capers, he discovers he has a talent for the work and quickly becomes involved in more dangerous and violent crimes. In November 1820, he’s accused of participating in a major highway robbery. And after this, his face appears on wanted posters all across Puerto Rico.

Roberto is forced to go into hiding. He evades the authorities for over six months, until he is arrested and sent to prison in July 1821. But just a month later, Roberto escapes and then disappears. His whereabouts over the next two years are something of a mystery, but when he resurfaces in June 1823, he’s put life as a highwayman behind him.

He’s not changed his ways however—only his targets. Now 32 years old, Roberto manages to source a small ship and a crew to sail it, and he wastes no time in making a name for himself on the high seas as a pirate. In a series of daring raids, Roberto and his crew attack and plunder eight vessels before the year is out.

But his success is an affront to the Puerto Rican government. A century has passed since the so-called Golden Age of Piracy, when famous outlaws like Blackbeard and Anne Bonny terrorized the seas. These days, the Caribbean is supposed to be a respectable, law-abiding place.

So, the government sends agents to Roberto’s hometown of Cabo Rojo. But getting useful information proves almost impossible. As a local boy, Roberto already has deep ties in the community, and he’s secured their loyalty even further by sharing some of his loot. To many in Cabo Rojo, Roberto is the Robinhood of the high seas.

But his popularity doesn’t deter the Puerto Rican government, and the hunt for Roberto intensifies. He doesn’t discriminate in his attacks—he takes Spanish, British, and American ships alike. So, as the problem of apprehending him grows, the Puerto Rican governor reaches out for help to those nations, and Great Britain and the United States both send ships to join the hunt.

So now, with so many forces arrayed against him, it seems only a matter of time before Roberto is captured. And sure enough, following a storm in September 1824, his ship runs aground on the eastern shores of Hispaniola, and Roberto is arrested. But Roberto refuses to give up. He escapes from captivity again in a daring prison break in which he uses a rope made from his clothes to lower himself down from a perimeter wall.

This escape only adds to Roberto’s reputation as the greatest living Caribbean pirate. But his growing renown will make his enemies that much more determined to bring him to justice. And less than a year after his dramatic escape from jail, Roberto Cofresí will be cornered for the last time.

Act Two

It’s March 5th, 1825, in Jobos Bay off the south coast of Puerto Rico, six months after Roberto Cofresí escaped from prison for the second time.

Standing on the deck of his ship, the Anne, Roberto slides his pistol out of its holster, checks that it’s loaded, and then gazes out over the prow at his next conquest. It should be an easy day’s work for Roberto—the merchant vessel making slow headway ahead of them will only be manned by a handful of sailors, who’ll be no match for a ruthless crew of pirates. Roberto orders his boarding party to stand by the rails, telling them to be ready to leap across as soon as they’re close enough.

But as the gap between his ship and the merchant vessel closes to less than a hundred yards, Roberto sees a flurry of movement on the other deck. Too late, he realizes he’s been duped. This is no ordinary merchant ship.

Rows of US Marines and Spanish militia suddenly leap out from hiding places, and appear ready on deck. As one, they raise their rifles and take aim at Roberto’s ship. Roberto ducks down as bullets crack through the air like whips, peppering the Anne and shredding its sails.

Roberto’s battle-hardened crew quickly returns fire, and a sea battle begins. But it soon becomes clear that this is a fight Roberto can't win. There are too many enemy soldiers, and the merchant ship has been equipped with a six-pound cannon. One blast from it has already brought down the Anne’s mast. Another direct hit could be disastrous. So, Roberto orders his men to abandon their weapons and, instead, concentrate on making their escape.

Still under heavy fire, the Anne manages to make a turn and darts away from the other ship. But its rigging is torn to pieces, and Roberto doesn’t know how long its damaged mast can hold out. He decides their best chance is to make for land and try to escape through the mangrove swamps. But the retreat isn’t without casualties. Two of his men are shot and killed before they reach the beach. The rest make it ashore and disappear with Roberto into the thick underbrush.

But they are soon followed by the American and Spanish soldiers who are hot on their trail. Over the course of the afternoon, around half of Roberto’s crew are captured in the swamps. Roberto himself escapes several brief skirmishes unscathed and survives the night hiding among the mangroves. But the following morning, he's spotted. And as he turns to flee, he's hit by a blunderbuss shot that knocks him to the ground and shatters his left arm. Gritting his teeth against the pain, he drags himself up and unsheathes his knife. But he is soon surrounded by machete-wielding militiamen. By the time Roberto finally surrenders, he is badly injured, and bleeding profusely.

Once in custody, Roberto is taken to a jail in the nearby city of Guayama, where a doctor tends to his wounds. While he's being patched up, the town’s mayor comes to see his illustrious prisoner. Roberto tries to work his charm on the politician, offering him a vast bribe of over thirty pounds of silver in exchange for his freedom.

But the mayor won’t be bought with stolen treasure. He simply shakes his head and walks out. Four days later, Roberto is transported to Puerto Rico’s capital, San Juan, where he will stand trial.

On March 17th, 1825, Roberto stands in a court house alongside ten of his crew. Under a new edict from the Puerto Rican governor, they are being tried in a military court. And under its rules, Roberto can choose an attorney to represent him, but the arguments they can make will be strictly limited, Roberto is even denied the opportunity to summon witnesses.

But he does give evidence himself. When questioned under oath, Roberto confesses to capturing a number of ships, as do his men. But he refuses to give any information about the whereabouts of those of his crew who escaped and remain in hiding.

So after ten days, the court announces its decision: all 11 men are found guilty of piracy. It's a crime punishable by death. There will be no appeals and no escapes this time. In just two days, Roberto Cofresí will face a firing squad.

Act Three

It’s the morning of March 29th, 1825, in San Juan, the capital of Puerto Rico, three weeks after the capture of the pirate Roberto Cofresí.

At the local fort, a large crowd has gathered to witness the execution of Roberto and his crew. And a little after eight AM, there’s movement off to one side of the yard. The crowd parts as a group of soldiers marches forward, herding a procession of shackled prisoners.

The convicted pirates are ushered toward a row of chairs, and one by one, they are pushed down into them and tied in place. From his seat in the center of the line, Roberto looks out at the crowd with defiance in his eyes.

Several priests step forward to hear any last-minute confessions. But when he's asked, if he has anything to repent for, Roberto shakes his head and fixes his gaze on the line of musket-wielding soldiers standing opposite him.

When the priests have finished their duties, they step back and take their places in the waiting crowd as blindfolds are placed over the condemned.

Roberto watches as his men have their eyes covered, but when the soldier reaches him, he again shakes his head. When a soldier tries to cover his eyes anyway, Roberto jerks his head back, and speaks in a loud, clear voice.

“I have killed hundreds with my own hands, and I know how to die.”

The soldier nods grimly and steps back. Then the men in the firing squad lift their weapons to their shoulders. Gunfire cracks the silence of the morning, and Roberto and his men slump forward, lifeless, in their chairs.

Roberto Cofresí will be seen as the last successful Caribbean pirate. After his death, the authorities will sweep the seas clear of any who would follow his example. But that will only make Roberto seem more alluring. Myths will develop about him in the years following his execution, with some even claiming it was a deal with the devil that allowed Roberto to evade capture for so long. But if that was the case, the deal came to an abrupt end when Roberto Cofresí was captured for the last time on March 5th, 1825.

Outro

Next on History Daily. March 6th, 1933. First Lady of the United States Eleanor Roosevelt hosts her debut press conference, inviting only women reporters in a practice she will continue for the rest of her time in the White House.

From Noiser and Airship, this is History Daily, hosted, edited, and executive produced by me, Lindsay Graham.

Audio editing by Muhammad Shahzaib.

Sound design by Gabriel Gould.

Supervising Sound Designer Matthew Filler.

Music by Thrumm.

This episode is written and researched by Rob Scragg.

Edited by Joel Callen.

Managing producer, Emily Burke.

Executive Producers are William Simpson for Airship, and Pascal Hughes for Noiser.