As is known, one of the reasons for the failure of Cuba’s Ten Years’ War against the Spanish colonial power (1868-1878) was the small number of expeditions to land on the Cuban coast with military supplies for the Liberation Army. The Cuban revolutionary leadership in exile was aware of this, and from 24 February 1895, the date on which the independence struggle broke out for a second time, it assigned priority to the task of importing supplies for the revolutionary forces. Efforts were concentrated in the United States and came mainly from among the tobacco workers, though other elements of the Cuban émigre population were involved to a lesser extent. To make the enterprise more effective, an Expeditionary Department was created, with a constitution approved on 2 August 1896. Colonel Emilio Núñez was placed at its head.

Among the ranks under his command, special importance was attached to those who were to command ships, since they would be responsible for their vessels’ safe passage - not just in the face of harsh sea conditions, but also if confronted by United States and Spanish gunboats.

Foremost in these duties for his skill and daring was a captain of Irish origin, John "Dynamite" O’Brien. Recruited by John D. Hart, he joined the Cuban struggle in early 1896. As owner of the steamer Bermuda he was able to use the ship for transporting supplies to the independence forces. He had accepted the contract ‘more out of sympathy with the Cuban cause than for the small amount of money that was offered’. Nevertheless, he took his duties so seriously that he replaced the entire crew and ‘not even to his own family did he confide his commitment or whereabouts’ (García del Pino 1996:46). In order to put the United States authorities off track, supplies were shipped in boxes labelled as medicine or codfish. O'Brien had already been accused of filibustering and sent for trial. Yet undaunted and in spite of constant surveillance by the United States police, he decided to undertake the difficult task of bringing to Cuba Major General Calixto García, one of the leaders of the Cuban Revolution.

The researcher Gerardo Castellanos has described the dangers of the crossing:

On Sunday Captain O’Brien on the 'Bermuda' calmly set out through the narrow bay, bound for Veracruz. He was soon surrounded by a number of tugs bearing customs officers and newspapermen, all hopeful of taking the expeditionary force by surprise. These were disappointed however, as the cargo had been carefully hidden. At Sandy Hook the curious were dispersed by a snowstorm. O’Brien took the opportunity to head east, and only when he was so far out from land that not even the smoke from his funnel could be seen did he take his true course south, heading towards Atlantic City. The rest of the expedition had been assembled in that city, to leave from there on Monday morning, the sixteenth. […] These took to a fishing boat in Great Egg Harbour and unfurled the agreed sign, a white flag. The transfer was carried out so speedily that it went unnoticed by anyone in the vicinity, and when the police’s suspicions were aroused the Bermuda had already been at sea for four days (Castellanos García 1927: 166).

During the voyage, the Irish captain made good use of his navigational skills, bringing the expedition to a safe conclusion by landing on 24 March 1896 near the city of Baracoa, in the extreme east of the island of Cuba. The shipment consisted of 3,000 rifles, a million rounds of ammunition, two artillery pieces, a printing press, revolvers, medicine and food. A few months later these supplies were to enable Major General Calixto García to mount an offensive in Cuba’s eastern province.

Francesco D. Pagliuchi, an Italian crew member, described the scene as they made land:

The dark ship […] was surrounded by a flotilla of small boats, moving rapidly like an army of ants. Each one bore away its arms and returned to get more. A subtle breeze from the coast wafted tropical fragrances towards us. In a few hours the men had finished their work. We would have loved to shout 'Viva Cuba Libre!' at the top of our voices, but we were only a couple of miles from the port of Baracoa. We contained our enthusiasm and left as silently as we had arrived (Pertierra Serra 2000:80).

By June, O'Brien was captain of the steamer Comodoro, and had signed on for another expedition. This time he brought to Cuba 400 rifles, 500,000 rounds of ammunition, 300 machetes, 2,500 pounds of dynamite, an electric battery, 5,000 feet of wire cable, together with medicine, surgical and other equipment (García del Pino 1996: 55). Again in August the tireless Irish seaman set out for Cuba. Commandeering the Dauntless he landed on the coast of Camagüey 1,300 rifles, 100 revolvers, 1,000 machetes, 800 pounds of dynamite, 46,000 rounds of ammunition, an artillery piece, a half tonne of medical supplies and several hundred saddles (García del Pino 1996:60).

O'Brien was to undertake another voyage to Cuba in March 1897. He set out from Cayo Verde, at the southern tip of the Bahamas, as captain of the steamer Laurada. A number of distinguished crewmen were on board: generals Joaquín Castillo Duany and Carlos Roloff; José Martí Zayaz Bazán, son of José Mártí, Cuba’s national hero, together with the internationalist Alphonse Migaux, a veteran of the Franco-Prussian War who had made his military skills available to the Cubans. On this occasion, too, the supplies transported were substantial: 2,050 rifles, 1,012,000 rounds of ammunition, two artillery pieces, 3,000 artillery rounds, 3,000 pounds of dynamite, 750 machetes, a machine-gun, torpedoes, clothing and other materials. The shipment was used in the assault and capture of the city of Las Tunas under the command of Lieutenant General Calixto García. This event contributed greatly to the resignation of the infamous Valeriano Weyler, the infamous head of the Spanish government on the island.

“Dynamite” almost lost his life in one of those perilous voyages. He left for Cuba on 22 January 1898 aboard the steamer Tillie, a small, dilapidated vessel. Forty-seven miles out from the United States coast, she began to founder. The crew took to the boats. Pagliuchi described the fateful moments:

On my boat were Captain O’Brien, the captain of the ship, several sailors and a few Cuban volunteers - fourteen in all. After we had moved away from the ship the captain, upon seeing that she was not sinking as fast as expected, urged us to try to save her […] Once the boat was salvaged, O’Brien ordered us […] to push her forward. We rowed for five endless hours in the face of fifteen-metre high waves, until we saw the largest sailing ship then afloat: the 'Governor T. Eames', a fine ship […] she was coming to rescue us. Finally, the 'Tillie' was swallowed up by the waters (Pertierra Serra 2000: 91).

But nothing would stop the intrepid Irishman. He resumed his freedom-fighting adventures on 14 February 1898. At the helm of the Dauntless, he arrived uneventfully to the coast of Camagüey. On this occasion the expeditionary force was composed of 24 men, among them general Eugenio Sánchez Agramonte. Yet again the revolution was furnished with large quantities of war material, thanks to “Dynamite” and his decision to serve the Cuban revolutionary cause.

Once the 1895 campaign was over O’Brien piloted the steamer Wanderer to Pinar del Río, in the west of Cuba. Mission accomplished, he returned to Key West. However, shortly before the conflict ended, O’Brien was one of the protagonists of the epic of the ship Three Friends. Let us return to the testimony of Pagliuchi, who accompanied O’Brien on that voyage and left an account worthy of a movie script: