Volume 7, Number 3

March 2010

Download pdf

Table of Contents


Contact Information

John O’Brien: Captain Dynamite
of the Cuban War for Independence, 1868-1898

By Herminio Portell Vilá [2]

Translated by Karen Racine


This article, written by noted Cuban historian Herminio Portell Vilá as one of a series of biographies of Cuban patriots and heroes of Pan-American solidarity, traces the swashbuckling adventures of John O’Brien, the feisty sea captain who ferried Cuban republicans from the US and the Caribbean coast to serve the nationalist cause. In his characteristic storytelling style, professor Portell Vilá recreates the personality and activities of this colourful son of Irish immigrants and reveals just how deep the love of liberty lay in his breast.

The revolutionary effort of Cubans to achieve their independence was prolonged for much more time than should have been necessary, and it required far more heroism and greater sacrifices than that of any other people of the Americas. During the course of nearly one hundred years, Cuba was in continuous political tumult, marked by both smaller, abortive conspiracies and larger-scale attempts to throw off the Spanish colonial yoke. Because Spain had lost the majority of its New World dominions during the first third of the nineteenth century, it had learned its lesson well and went on to concentrate all remaining resources in Cuba, along with an intensified hatred of republicanism and all that was American. With jealous zeal, the Spanish Crown’s most characteristic strategy was to keep Cubans out of the armed services and to render it impossible for their sons to become sailors. The imperial government dared not manufacture any guns, sabres, or munitions on the island itself; all weaponry had to be brought to Cuba from abroad through official Spanish channels. Its aim was to maintain domination over a docile and disarmed population. Cubans should be kept unfamiliar with the technical knowledge of warfare and lack access to such maritime communication as would be indispensable for any successful rebellion. This imperial monopoly over the trade in arms and explosives characterized a regime of externally-controlled defense that left the average Cuban to his own devices when personally threatened or when contemplating a rebellion. For example, the machete was a key tool for agricultural workers, but in the hands of the mambises [a colloquial name for Cuban revolutionaries], it could be turned into a terrible weapon.

Cuban uprisings, therefore, have always depended on military expeditions that were organized and equipped abroad. These ragtag ventures had to alight at remote spots along the coast with the goal of linking up with patriots in order to provide them with arms, and to stage their surprise attacks. From the infamous ‘Expedition of the Thirteen’ in Bolívar’s days (1826) throughout the course of the entire nineteenth century, all Cuban revolutionary movements needed outside assistance. This was the case with the secret Masonic lodges known as ‘Los Soles y Rayos de Bolívar’ and ‘La Cadena Triangular y Soles de Libertad’, and with the many attempts of the filibuster Narciso López and his followers, up until 1868. Similarly, the sustained guerrilla effort of the Ten Years’ War (1868-1878), the Guerra Chiquita (1879-1880) and, finally, the last and definitive push for independence between 1895 and 1898 all had crucial contacts and assistance from abroad. In fact, Cubans would have freed themselves much earlier if they had actually received all the war materiél that they had bought but which had never made it to the island due to having been confiscated in the United States or in British Caribbean colonies, or having been lost at sea, or because the cargo was captured by the Spaniards. The failure of their many attempts, on the other hand, was almost always also the failure of one or more Cuban amateurs who had been trying to prepare themselves as navigators. On many occasions these men paid with their lives – they were shot, hanged, or garrotted for struggling for their homeland’s liberty. For all these reasons, it was difficult for Cubans to acquire sufficient technical knowledge to head out on the open sea with confidence and strength. Gunrunning in support of the Cuban mambises was one of the riskiest endeavours along the margins of Caribbean society.

Throughout the nineteenth century, the United States government was showered with constant denunciations from the Spanish Legation in Washington which consistently invoked neutrality laws and international treaties in order to curb illegal trade of all kinds to Cuba. Its agents operated throughout the major cities of the eastern seaboard from New York to Key West to New Orleans, all of whom actively worked to impede the many expeditions that were outfitted on those shores. But, even if the United States federal government relaxed its vigilance or showed any sympathy for the organisation of expeditions headed to Cuba, the rebel exiles were also being shadowed by implacable and untiring spies in the service of Spain; many of these ‘gumshoes’ belonged to the Pinkerton Detective Agency with salaries paid directly from Cuba using contributions that the colonial government managed to extract forcibly from the islanders themselves. [3] The mid-nineteenth century was a time of dramatic struggles all throughout the independent Latin American republics. There were inter-American border wars that fuelled lucrative businesses for the daring navigators and their supplies, and whose personnel were often drawn from the margins of the law. These men were known as filibusters and, without a doubt, they revelled in the memory of those valiant highwaymen of the seas, the pirates, who had been the first to rise up against colonial arbitrariness and who had challenged the power of the great European nations. Indeed, the pirates almost managed to establish their own independent republics governed from their Caribbean island haunts.

A Pirate’s Life for Me

Captain John O’Brien of New York had made a notorious career of gunrunning and the conduction of dangerous cargo to its intended destination, no matter where it might have originated.  Born in the heart of the docklands and shipyards of New York’s East River, the earliest memories he had were those of the sea and sailboat, not of his parents or home environment.  Little Johnny O’Brien, the son of Irish immigrants who worked on the docks, first crawled and then ran around the workshops, climbed the walls, skipped up the steps, and explored the ships under construction;  he never refused a ride on a motorboat or the ferries, and especially loved the big boats on which he worked as a cabin boy.   As he grew older, he studied navigation, and eventually graduated as a ship’s pilot.  ‘He was very skilled, dedicated and worked harder than anyone else, this Johnny O’Brien,’ the old ‘sea dogs’ pronounced sententiously, ‘but he had something of the Devil in him.’  Obstinate, determined and somewhat  of an evil genius, prone to fighting, he was not born for a tranquil life.  His daydreams were those of Captain Kidd.  For him, there was no law except his own, and he knew no other way to react against injustice except with violence.

In effect, the reputation that Johnny O’Brien had achieved by age of twenty-five was that of a fearsome man, full of generous impulses and capable of throwing himself enthusiastically into whatever noble cause he found until he reached the sacrificial end.  O’Brien had two supreme and overriding loyalties, one to his boat and the other to the sea itself.  All other loyalties, including patriotism, he understood in his own particular way.  He could switch sides in various conflicts.  For example, Johnny O’Brien, named third official on the cruiser Illinois of the United States navy, participated in the famous battle attack on the USS Merrimack when the confederacy raised and rebuilt it in1862, but he became upset with the Admiral Louis M. Goldsborough’s caution and discharged himself;  a  few months later, O’Brien had signed on as commander of the South’s brigantine Deer in which he brought a cargo of arms and munitions from New York to Matamoros in Texas for the confederacy, outwitting a federal blockade. [4] He always considered this episode to be a supreme demonstration of his unrivalled sailing ability.  Later on, as pilot for the Port of New York, O’Brien’s skill confirmed his reputation as a daring pilot; he knew the coastline like back of his hand and understood the treacherous currents of Hell’s Gate on an intuitive level.  O’Brien was soaking wet much of the time and, despite stormy seasons, he never hesitated to bring to port or take out to sea any boat that was entrusted to him, and he never had a single accident.  Around 1871, all the toughest piloting jobs were left to Johnny Daredevil, or Fearless Little Johnny, as he was then called, a young man with muscles of steel and unequalled competence.

Ship-owners themselves came to prefer Johnny O’Brien as their captain on difficult routes, secure in the knowledge that he always made it to port with their boats.  There were times when he was in command of two ships at the same time, the General Washington and the General Cromwell, both of which trafficked between New York and Halifax.  Difficult or insubordinate crews were not a problem for him;  besides being a strict disciplinarian, he earned respect and loyalty for the generosity with which he treated his subordinates.

With the fame he so richly merited, ‘Johnny Daredevil’ was put in command of the steamship City of Mexico in 1885.  He was hired by Colombian revolutionaries from New York with an expedition destined to overthrow President Dr Rafael Núñez who had been elected as a liberal, but went on to embark upon a programme of conservative centralisation, perhaps even a dictatorship. [5] As O’Brien had already demonstrated in his own country, he was not given to a preoccupation with the niceties of who was in the right up until that point in his life.  He had fought for both the North and the South during the United States Civil War, and in the same vein now, he was allying himself with Colombian liberals against the reactionaries.  Because of his indifference towards issues of justice and sectarian politics, the crew of the City of Mexico signed up in the belief that they were engaging in a legitimate commercial trip to Jamaica, and then found themselves one day on the coast of Colombia. Yet this new adventure would awaken O’Brien’s interest in the many other similar voyages all along the Atlantic coast of the United States, and once he found his true cause, he came to be known as the sailor who never backed down in the face of anything.

An Irish American Comes to Cuba

A short while later, Johnny O’Brien made his first contacts with Cuba and the Cubans.  The City of Mexico, ostensibly chartered for the transportation of bananas, coconuts and tropical fruits throughout the Caribbean, began to visit Baracoa and other ports of the island.   Its explosive captain, O’Brien, had to deal with the corruption and the despotism prevailing in all parts, and he began to sympathize with a tyrannised people whom he found to be both liberal and hospitable.  Using the cover of each legitimate trip that he conducted, O’Brien also brought in his contraband small quantities of arms and munitions  that were destined be put to use in the little revolution that was slowly starting to take shape.  Somehow or another, the Spanish authorities discovered that O’Brien was up to something other than simply buying Guinean bananas and coconuts; the sea wolf understood that the best thing to do would be to suspend his voyages and avoid complications.  His sympathies for the Cubans, however, began to grow in the same proportion to his hostility for the Spaniards.

Toward 1887, the City of Mexico passed into the hands of the President of Honduras, Marco Aurelio Soto, friend and protector of Antonio Maceo, Tomás Estrada Palma and other Cuban patriots. [6] O’Brien was contracted to captain a ship to carry a revolutionary expedition; the plan failed when English authorities intercepted information in Jamaica, but the exiles reorganised themselves with a new plan.  The already well-known contrabandista captain was put in command of the Norwegian steamship Fram which he took to the Turks and Caicos Islands north of Hispaniola; there he joined the expeditionaries intending to invade Honduras in order to restore Soto to the presidency.  O’Brien was not a man of many scruples, and his passengers did not like him, with the exception of three, all Cuban veterans of the Ten Years’ War who were in Central America as professional soldiers.

‘How is it that you joined up with this mongrel group who promised you land if you would fight?’ he asked the Cubans one night while sitting in the cabin drinking coffee.  He added ‘I could tell that you are the best element of those desperate adventurers from a mile away.’

Their response: ‘We have no other thought but the liberation of Cuba, and we need to be able to count on a base of operations near the island, maybe even in Central America.  The revolutionary preparations had just finished and more were being made in New York, New Orleans and Jamaica.  Precisely because of the lack of outside aid, now we are dispersed and we will be roaming until the struggle calls us home again.  We have already fought once before, alone, over the course of ten years, in order to liberate Cuba, and we will return to do it again.  However, our great difficulty and major stumbling block is that we have to import arms and munitions from the United States, evading the vigilance of the North American authorities, the Spaniards, and the spies in the service of Spain’.

The Irish-American sat silently for a long time, thinking.  Finally, he said solemnly, ‘If you need an expert sailor to be a filibuster one day, remember Johnny O’Brien. I also want to come to the aid of Cuba.’   During the course of his time in Soto’s Honduran service, O’Brien came to know Antonio Maceo, the great Cuban patriot whose integrity, discretion, and bearing made an excellent impression upon him. [7] Maceo and his Cuban compañeros received early proof of O’Brien’s friendship when he refused to permit a Spanish cannon to pass between the island of San Andrés and the Honduran coast in order to assure himself that the expeditionaries were not going to Cuba.  This event may perhaps have contributed to the chain of events that culminated in the arrest of the caudillo and his compatriots.

Lighting ‘Captain Dynamite’s’ Fuse

Upon returning to New York, a new adventure awaited Johnny O’Brien, one which would give him his nickname for life.  A Cuban merchant established in Panama negotiated the purchase of seventy tonnes of dynamite in the US city, but did not have a ship that was willing to take a cargo of explosives on such a dangerous passage.  Juan O’Brien was already well-known among the Cubans, and, therefore, he was the one to whom they confided the voyage; it took place in the middle of tropical storms which threatened the ship with destruction at any moment. Fortunately, the journey went off without a hitch.  The Rambler’s dangerous cargo had been the talk of the town among all the seagoing folk from Boston to Philadelphia.  When the merchant received notice that his seventy tons of dynamite had arrived safely in Panama, he decided that it was no longer sufficient to call the skilled captain ‘Johnny Daredevil’;  from then on he would be known as ‘Captain Dynamite’.  This is how John O’Brien has come to be remembered in Cuban history.

Captain O’Brien’s last filibustering service before enlisting himself in the Cuban expeditions was that of bringing arms and war materiél for General Louis Mondestin Florvil Hippolyte’s faction in Haiti.  He forcibly conquered power and expelled his rival. The General offered O’Brien the chance to be to be named admiral of the tiny Haitian navy, but he flatly refused. O’Brien was one of the better-known sailors along the routes between the United States and various Caribbean islands, and his knowledge was invaluable.  Captain Dynamite knew where rebels could take refuge at any given moment.  For that reason, and many others, he was an irreplaceable aid to the Cubans.

Joining the Cuban War for Independence

The first expedition of the War of 1895 was that of La Fernandina, which ended in a much-talked-about failure that had the effect of breaking down the revolutionary preparations that José Martí, Máximo Gómez and Maceo had made with such care.  The Amadis, the Lagonda, and the Baracoa were detained by the North American authorities by virtue of a betrayal that was quickly followed by insistent complaints from the Spanish ambassador in Washington.  Rifles, revolvers, machetes, munitions and other war materiél that had been bought with funds cobbled together one peso at a time, often through patriotic donations of mere pennies, were confiscated.  This was an early, and definitive failure of the first stage of the movement. Cuban patriotism then went on to initiate its revolution with almost no arms at all.  Its chiefs, Martí and Gómez, headed for the island in a little more than a rowboat with four more compatriots.  Antonio Maceo and Flor Crombet, went separately with a group of twenty-three other patriots.  They were the first and poorest expeditionaries who came to Cuba, and it seemed to point to a repeat of the setbacks that had plagued previous attempts.  In the United States, however, an ad hoc Department of Expeditions had been organised among Cubans, headed by Colonel Esteban Núñez, a veteran of the Ten Years’ War.  Other Cubans joined and aided them upon arrival, most of whom had knowledge of navigation and machinery that was little more than elementary.

It was not until the end of July 1895 that the mambises received an expedition of importance, which was that of Carlos Roloff, disembarked near Tunas de Zaza and which brought with it three hundred rifles, three hundred machetes, and corresponding munitions.  One hundred and fifty men, under the command of General Serafin Sánchez, incorporated themselves with the disembarked group.  Later on, several ships arrived and their passengers disembarked, including: the León at the Punto de Taco in Baracoa, Carlos Manuel de Céspedes in the Laureada at La Caleta in Baracoa, and General Francisco Carrillo in the Horsa, at Cabañita which was a small dock joined to the fort of La Socapa, Santiago de Cuba.  Even with the influx of men and armaments, they still would not have been able to secure the island’s independence,  had not been for the heroism with which the Cubans met their challenge.  With their limited supply of guns and ammunition, it would have had been impossible to carry out the invasion.

Gómez and Maceo made frantic demands to delegate Tomás Estrada Palma to send them arms and materiél.  Their letters arrived at the offices of the Cuban Revolutionary Party in New York, painting with sombre colours the situation of an army that was carrying out such a portentous deed almost entirely unarmed. Estrada Palma and Emilio Núñez struggled with the lack of resources, but worried even more about the difficulty of obtaining good boats and personnel who could be trusted.  Espionage had infiltrated the ranks of the revolutionaries, many of whom had practically sold themselves to Spain.  In one notorious case, the captain of the Commodore had been bought for $5000; he revealed in advance the place where his expedition would disembark.  When Calixto García embarked with his men on the steamship Hawkins in January 1896, a traitor opened the floodgates and the boat sank with the loss of ten lives and all the valuable cargo. A few days later, in the middle of New York harbour, Calixto García and his companions were arrested on board the Bermuda, after Spanish agents made a complaint when they were about to raise anchor.

The consternation was general among Cuban emigrés.  Violent attacks were directed against Estrada Palma and his auxiliaries.  The expatriate community held them responsible for these expensive disasters, while the mambises in Cuba frantically and futilely cried out for arms.  The press continually  published  information on the activities of the Cubans and their friend Johnny O’Brien.  For his part, Captain Dynamite, reading the newspapers while seated in the doorway of his house in Arlington, New Jersey, on the outskirts of New York, despaired in the face of these failures.

One night, speaking before various compatriots, he declared ‘I affirm that it is possible to bring expeditionaries to Cuba, despite the vigilance of the federal agents and the many spies that infest these territories.’

‘I don’t suppose that you are thinking of returning to filibustering and coming to the aid of the Cubans,’ ventured one of his friends, while O’Brien was taking furious draws on his pipe.

‘Well, then, it would not upset me to do that,’ Captain Dynamite replied.  ‘In the first place, I don’t have many good memories of the Spaniards, and the life of a pilot in port is very monotonous. For a long time now, I have had genuine sympathy for the idea of Cuban independence.’

‘John,’ said another of his friends, ‘I know Mr John D. Hart, the owner of the Bermuda, and I am going to tell him about our conversation.’

On the following day, 14 March 1896, Mr. Hart came calling upon Johnny O’Brien, after having consulted with the chiefs of the Cuban emigrés, who eventually confirmed their faith in Don Tomás [Estrada Palma] after an acrimonious debate.
‘Captain,’ Mr. Hart began to say, ‘I have called upon you today to discuss how we can aid Cuba by bringing General García’s expedition there.  The recent setbacks and betrayals have produced such an effect upon the Cubans that, unless General García arrives in Cuba with his arms, the general reticence of the contributors who live there will become a real danger.  If we cannot get the General there, the Cuban fighters will wait defenceless and eventually will have to surrender or be killed.  I have a good boat, and I am disposed to risk it in the hands of a man of resolve, loyal and able, like yourself.  I cannot offer much for your services, which may end up costing you your life.  The revolutionary treasury can offer you $500, but there is glory in this enterprise itself, aiding a people struggling to be free.’

‘Mr. Hart, the economic part of your offer does not interest me,’ responded O’Brien.  ‘Yes, I am happy to help the Cubans’ cause.  Years ago, I offered myself to the revolutionaries, among them General Maceo, and the only thing I regret is that this invitation has been delayed so long.  You can count on me.’

‘When will you be ready to set sail?’ Mr. Hart enquired.

‘I am ready to go right now,’ was the response.  ‘Despatch the ship as if it were going to Veracruz, and we will leave tomorrow morning.  Tell General García and his men to go to Atlantic City by train that same night and I will pick them up by boat along the coast.  They should go by the last train so that they will not have to linger too long there, and they should keep away from the town.  You can get a little rowboat on shore to take them out to sea where they can board the Bermuda, which will be waiting there for them.  If all goes well, the ship will be there in front of Atlantic City tomorrow around noon.  If a coast guard vessel follows us, I will take measures during the day to shake it off before nightfall. Then Monday morning we will take the general and his companions on board.’

All went according to plan.   The Bermuda was loaded up with war materiél when it left New York, supposedly heading for Veracruz.   Surreptitiously, the Cuban revolutionaries slipped on board near Atlantic City and headed off toward Cuba.  Coming face to face with Captain Dynamite, Calixto García said to him, with the same pessimism that had dominated his previous reversals in fortune, ‘I never thought that I would see Cuba again.’

‘Do not worry about that, General,’ said O’Brien.  ‘This time you will disembark in Cuba.’

‘That is what they all said,’ replied the old soldier.

‘But I have never been the one to make that promise to you, have I?’ interrupted the old sea dog.

‘Certainly not,’ admitted García.

‘Well then, accept my word of honour.  This time you will return to your fatherland.’

Two weeks later, in Marabí, Baracoa, General Calixto García returned to Cuba, after an absence of many years and having been taken out of the country as a prisoner. A good number of patriots disembarked with him, along with more than twelve hundred guns intended to energise the revolution.  After the brief stopover, as he was bidding goodbye, Calixto García became overwhelmed with emotion when he said to O’Brien, ‘Captain, you have kept your word.  Where others lied to me, you did not.  We will never forget you.  I hope that you will continue in the service of Cuba, because we need it.’

Devoted Until the End of His Days

The Bermuda returned to the seas and returned to the United States, where O’Brien was charged with being in violation of the North American neutrality laws.  Estrada Palma received Captain Dynamite as a hero, which, in fact, he was, and the exiles’ Revolutionary Delegation invited him to join their work as chief of navigation.  Johnny O’Brien accepted their offer, with the declaration that he was doing so because of the sympathy that Cuba’s cause inspired in him.  Almost immediately, the Spanish espionage network discovered that the famous filibuster had come to an agreement with the mambises and made him an object of careful surveillance.  One day, Mrs O’Brien doused one of these thugs with boiling water when he lingered outside;  others were caught in the terrible bear traps that Captain Dynamite had set out in the yard when they tried to sneak into her house.  In both cases, before freeing the busybodies, O’Brien told them, in the most energetic terms, what he thought of Cuba’s Governor Valeriano ‘the Butcher’ Weyler, of the Spanish Minister in the United States Enrique Dupuy de Lôme, of Spanish Prime Minister Antonio Cánovas del Castillo, and of the Spanish colonial regime in general.  He made them promise to repeat his words to their superiors when they reported the misfortunes they just suffered at his hands.

Cubans had been encouraged by the success of the Bermuda.  Following O’Brien’s advice, other smaller expeditions came to Cuba, and disembarked all or part of their cargo, but in order to maintain the war throughout the entire country, to complete the invasion, and to construct the trail, logistics demanded that the boats be much bigger. For these reasons, the foreign community organised new expeditions on the Laurada and the Dauntless, undoubtedly the most important ones ever despatched by the overseas Cubans. Before the aforementioned ships were sent out, however, the Irish-American Juan O’Brien had paved the way with small disembarkations which were ultra-useful, of men and equipment in various places throughout the island.  His had been a mere tugboat, but the man himself was to dedicated to bigger things.

In those days, Spanish diplomats, federal agents and spies of all types worked in conjunction to bring Captain Dynamite to trial for having violated the United States’ laws of neutrality.  But, wherever the picturesque sea wolf was betrayed to lawmen, juries declared him to be innocent.  He had always handled his affairs with great caution in order not to leave evidence that might incriminate himself.  Under O’Brien’s personal direction and others who acted according to his instructions, the expeditions continued to arrive in Cuba.  The available boats were old and almost unserviceable; some were mere tugboats which resulted in extremely dangerous adventures on the high seas.  However, Johnny O’Brien was never once shipwrecked while in the Cuban service and always made his haul with all possible precision.  The revolutionaries had twice risked their lives in order to serve their Fatherland, and they would stop at nothing to complete the task.

In December 1896, Captain Dynamite weighed anchor in the port of La Fernandina, carrying the expedition of Colonel Rafael Pérez Carbó, while some friends entertained the customs administrator with a game of poker.  The distracted official boasted that it was impossible to beat him.  This time, the expeditionary boat was just a little tug, the Three Friends, later to become famous as a filibuster’s ship; on board it had guns, munitions, machetes and a twelve-pound cannon called Hotchkiss.  On 19 December 1896, the Three Friends approached in order to obscure the predetermined rendezvous point for the disembarkation in the jurisdiction of Cienfuegos.  Johnny O’Brien was at the wheel.

‘Break port and head for the sea at full speed!’  shouted the old contrabandista.

‘It seems to me that you are outrunning a shadow,’ said Colonel Federico Pérez Carbó, one of the chiefs of the Department of Expeditions and who had not yet seen the enemy ship.

‘You think so?’ O’Brien laughed, ‘Wait a minute and you will see that I am right.’

The Three Friends barely escaped when a detonation exploded from the bow of the persecuting cannoner and lit a blaze.  The cannonball landed very close to the tug while O’Brien was saying to Pérez Carbó  ‘There we have what you had called a lively shadow, colonel.’  Almost immediately, two more Spanish ships appeared, making it evident that they had fallen into a trap intended to capture the Three Friends or else to sink it.  O’Brien ordered the cannon Hotchkiss to be armed at the stern, secured with rope, and aimed at their pursuers.  One of the sailors, Mike Walsh, had been an artilleryman in the United States navy, and he was put in charge of the cannon.

‘If you would permit me to handle it,’ said Walsh, ‘I guarantee that I will induce many pains in Spanish stomachs with these little pills.’

‘Ah, young man,’ O’Brien replied, ‘discharge the cannon as often as you can, because our lives depend on it.’           
‘Now this is glory!’ exclaimed Walsh, and then, taking the megaphone in his own hands, shouted in the direction of enemy boats, ‘Prepare yourselves for a burial at sea!’

In effect, shortly after the attack of the cannon Hotchkiss, he made his only shot which almost sank the Three Friends, but the grenade exploded with precision on the bridge of the cannoneer, which was a half a mile away, killing thirteen men and wounding a dozen more. With that, the persecution ended, and the small Three Friends continued its voyage until it discharged the expedition.

Governor Weyler’s rage knew no bounds.  A spy sent by his secretary Congosto offered the sum of twenty-four thousand pesos to O’Brien in order to discover the whereabouts of the next expedition.  The Dynamite Captain refused the bribe, and then brought the formidable Roloff-Castillo Duany expedition to Cuba on board the Laurada, which disembarked in Banes, and, without the loss of a single crate, turned over its cargo to the revolutionaries.

‘Captain O’Brien has eluded us until now,’ thundered a furious Weyler, ‘but that same audacity will allow him to fall into our hands.  Sooner or later we will capture him and when we do, instead of executing him as we will do with the Cubans who accompany him, we will hang him ignominiously from the flagpole of La Cabaña, in view of the whole city.’  O’Brien’s response was characteristic and elicited a great guffaw from his men, at Weyler’s expense. He taunted back:  ‘To show my disdain for you and for those you obey, on my next trip to Cuba I will disembark within sight of Havana. Maybe I will even enter into the bay itself and take you prisoner.  If I capture you, I will cut you to pieces and feed you to the boiler of the Dauntless.’

In the month of May 1897, in the Dauntless, O’Brien discharged half of his cargo at Nuevitas and took off with the rest, heading toward Havana, where he arrived on 24 May. Under the watchful eyes of the coast guard and garrison, he unloaded the other half a mile from El Morro. He had complied with his promise to Weyler.  Thus, this valiant and incorruptible man continued to risk his life for Cuba in boats great and small, under sail and steam, as many as he could charter, to carry arms, munitions, medicines, clothing, et cetera, to a people struggling for independence.  His name had been turned to a legend of unforgettable, heroic deeds.

On 15 February 1898, at the wheel of the Dauntless, O’Brien disembarked an expedition in Nuevas Grandes and, in the course of a few hours, landed another a little further along in the bay of Matanzas.  Upon his return, while he was in the Florida Keys, O’Brien learned of the explosion of the USS Maine in the bay of Havana, and quickly realised that open war between Spain and the United States would soon follow.  A few weeks later, at the beginning of hostilities, Estrada Palma put Johnny O’Brien, Captain Dynamite, in the command of the Alfredo, the first ship of war that flew the Cuban flag freely in foreign waters.  His plans had been devised specifically for O’Brien, so that he could dedicate himself to the service of the expeditions; chance of circumstances had converted it into the first boat of free Cuba. 

‘Now I sail under my own flag,’ said Captain Dynamite, gazing upon the Cuban flag flying proudly in the air. 

Johnny O’Brien, the intrepid Irish-American filibuster who had risked his life many times for the independence of Cuba, ended his long and illustrious career as a captain in the Cuban Coast Guard and Pilot of the port of Havana in the independent republic that he had helped to create,  but which never compensated him as fully as it should have.

Herminio Portell Vilá



1. The original article appeared as “John O’Brien, el Capitán Dinamita” in Herminio Portell- Vilá,  25 biografías de americanos ilustres, (Havana: Editorial Minerva, 1944), pp.353-367.

2. Herminio Portell-Vilá, (1901-1992) was a professor at the University of Havana, where he once taught a young Fidel Castro.   He left the country for Miami shortly after the Revolution, where he worked for the Voice of America, was Director of the American Security Council, and continued to write his historical studies.  Over the course of his long and distinguished career, he was the author of: Narciso López y su época (1930),  Céspedes: El Padre de la Patria Cubana (1933), Medio siglo de “El Mundo”: Historia de un gran periódico 1901-1951 (1951), Benjamín Franklin: El primer americano universal (1956), History of Cuba in its Relations with the United States (1973),  Nueva Historia de la República de Cuba (1990), and Finlay: Vida de un sabio cubano (1990).

3. The Pinkerton National Detective Agency was founded by Allan Pinkerton in 1850, and specialised in several nefarious jobs: infiltrating the work forces of factories and mining companies to root out potential unionizers, private military contracting work, and guard duties on the frontier.

4. See James L. Nelson, The Reign of Iron: The Story of the First Battling Ironclads, the Monitor and the Merrimack, (New York: HarperCollins, 2004).

5. Alberto Dangold Uribe, Rafael Núñez : regenerador de Colombia, (Madrid: Anaya, 1988);  James William Park,  Rafael Núñez and the Politics of Colombian Regionalism, 1863-1886, (Baton Rouge: Louisiana State University Press, 1985);   Gonzalo España,  La Guerra Civil de 1885: Núñez y la derrota del radicalismo, (Bogotá: Ancora Editores, 1985).

6. Darío A. Euraque,  Reinterpreting the Banana Republic: Region and State in Honduras, 1870-1972,  (Chapel Hill: Univ. of North Carolina Press, 1996);  Kenneth V. Finney,  In quest of El Dorado: Precious Metal Mining and the Modernization of Honduras, 1880-1900,  (New York: Garland Publishing, 1987);  Mario Argueta,  Cronología de la reforma liberal hondureña,  (Tegucigalpa: Univ. Nacional Autónoma de Honduras, 1982).

7. Philip Sheldon  Foner,  Antonio Maceo: The "Bronze Titan" of Cuba's Struggle for Independence, (New York: Monthly Review Press, 1977);  José Luciano Franco,  Antonio Maceo en Honduras, (La Habana, Unión Interamericana del Caribe, 1956).



- Ferrer, Ada,  ‘Rustic Men, Civilized Nation: Race, Culture and Contention on the Eve of Cuban Independence’ in  Hispanic American Historical Review 78, #4 (November 1998): 663-686.

- Franco, José,  Ruta de Antonio Maceo en el Caribe  (Havana: Nuevo Mundo, 1961).

- Hume, Edgar Erskine,  ‘Captain Thomas O’Hara and Cuban Independence, 1850-1851’ in Bulletin of the Pan-American Union 71 (1937): 363-367.

- Pérez, Louis A.,  Cuba Between Empires 1878-1902 (Pittsburgh: University of Pittsburgh Press, 1983).

-----.  Cuba in the American Imagination: Metaphor and the Imperial Ethos  (Chapel Hill: University of North Carolina Press, 2008).

-----.  ‘Cubans in Tampa: From Exiles to Immigrants 1892-1901’ in  Florida Historical Quarterly 57:2 (October 1978): 129-140.

-----.  ‘Vagrants, Beggars and Bandits: Social Origins of Cuban Separatism, 1878-1895’ in Hispanic American Historical Review   90, #5 (December 1985): 1092-1121.

-----.  ‘Tan cerca, tan lejos: Cuba y los Estados Unidos, 1860-1890’ in  Temas 8 (Oct-Dic 1996): 4-9.

- Poyo, Gerald  ‘Key West and the Cuban Ten Years’ War’ in  Florida Historical Quarterly 57, #3 (1979): 289-303.

- Roig de Leuchsenring, Emilio,  Cuba no debe su independencia a los Estados Unidos (Havana: La Tertulia, 1960).

- Schwartz, Rosalie,  ‘Bandits and Rebels in Cuban Independence: Predators, Patriots and Pariahs’ in  Biblioteca Americana 1:2 (1982): 91-120.

- Tone, John Lawrence, War and Genocide in Cuba, 1895-1898 (Chapel Hill: University of North Carolina Press, 2006).

Copyright © Society for Irish Latin American Studies, 2010

Published: 02 March 2010
Edited: 12 October 2010

Portell Vilá, Herminio, 'John O’Brien: Captain Dynamite of the Cuban War for Independence, 1868-1898' in "Irish Migration Studies in Latin America" 7:3 (March 2010), pp. 339-348. Available online  (www.irlandeses.org/imsla1003.htm), accessed .

The Society for Irish Latin American Studies

 Copyright Information