Dynamite Johnny O'Brien: 'A Captain Unafraid'

Note Johnny with the Piratic Bandana

Have a read below to find out more about this captivating, mad, "Irish-American Maurader!" This is a blog post from my own "Ildaite Blog" that I thought I'd share with you all. I am currently working on a documentary film concerning "Dynamite" Johnny O' Brien called "A Captain Unafraid." Here is a link to the facebook page for the film  "A Captain Unafraid" is currently being funded through Indiegogo. Here is the link to the "A Captain Unafraid" campaign. Share the links at will! 


Captain “Dynamite” Johnny O’ Brien was born in 1837, in the old dry dock section of New York, almost on the banks of the East River[i]. His parents hailed from Longford and Cavan, Ireland. “Being of Irish parentage I was favourably disposed towards dynamite on general principal,” he once exclaimed. Johnny learned to walk in a cradle of shipyards. He ran away to sea at the age of 13.[2]Though he began his career as a ferryman-guiding vessels over the notorious waters of Hell Gate, New York-he quickly became known as a filibuster, that is-an illegal transporter of arms. Johnny saw it as his patriotic duty to supply those in need with arms and ammunition–“We [Americans] should not forget that we were rebels once ourselves, and warmly welcomed filibustering aid from France.” Though Johnny was involved in revolution and ruction across the Americas, it was through his involvement with the Cuban War of Independence that he gained true fame, or perhaps, lasting notoriety.

Captain O Brien’s parents were most likely married in the parish of Killinkere, county Cavan. They were friends and neighbours of the parents of General Philip Sheridan who lived in that townland. General Sheridan was a leading figure on the Union side in the American Civil War. Philip’s birth is shrouded in mystery-as his mother seems to have fabricated a U.S. birthplace for him. She (and many others) hoped Philip might become president of the U.S.[3]

Dynamite Johnny received his sobriquet, not for the many tons of dynamite he ferried to Cuba, but for sixty tons he brought to Panama in 1888. Panama was part of Colombia at the time, and (according to Johnny) sixty tons of dynamite was enough “to blow the whole of Colombia off of the map.” This was before dynamite was de-natured; in other words, it could explode at the slightest jarring. A wealthy Cuban of revolutionary proclivities had purchased The Rambler (which was the largest yacht in New York Yacht Club). He intended to change the political map of Colombia and had also purchased 60 tons of dynamite to help him on his way. Having looked far and wide for a captain to ferry the dynamite (to no avail), the Cuban heard whispers of a daredevil[4] captain named Johnny O’ Brien. A meeting was arranged between the two and Daredevil Johnny “cheerfully signed up” for the job. The dynamite was loaded while the vessel was anchored at the Statue of Liberty and soon the expedition was well under way. The beginning of the voyage passed uneventfully, but when the yacht entered the Gulf of Mexico a savage lightening storm blew up. Johnny’s hair started to “crackle like a hickory fire” when he ran his hands through it. Every time he touched a piece of metal he felt a slight shock. Thinking it was his last moment on earth-from the corner of his eye-Johnny saw a spark alight-a sailor contriving to light his pipe. At this moment (having failed to inform his crew that the hold was full of dynamite), Johnny climbed down to the bottom of the ship and tied down the boxes of sudden death single-handedly (as they had begun to roll around). Eventually, the storm passed and they reached the port of Colon without further incident. When the sailors saw box after box being unloaded-emblazoned with the word Dynamite, Johnny said his crew would have ended his life, had they not been “suffering considerably from heart failure.”

Though Johnny looked for trouble and fortune on many’s the foreign shore, in his own country, he aided both the Confederate and Union causes in the American Civil War. He was appointed third officer of the Union ship The IllinoisThe Illinois (along with other vessels) intended to ram an “iron clad” Confederate warship-The Merrimac. This was the first iron steam ship built by the Confederates and was wreaking havoc off the coast of Virginia. Johnny received his officership at the tender age of 25, more for the kamikaze nature of the mission, than any perceived greatness the Union forces felt he might have possessed[ii]. At any-rate, the fracas never occurred, as General Goldsborough never ordered the Union fleet to engage the Merrimac. Johnny said of Goldsborough-“I do not like to call a dead man a coward but I will say that General Goldsborough was the most cautious and conservative American I have ever known.”

Hot on the heels of his station aboard The Illinois, Johnny’s next expedition was smuggling arms to his supposed enemy-the Confederate States of America, through the Mexican port of Matamoros. Once the arms arrived in Mexico, they were smuggled over the border to Brownsville, Texas. Johnny shipped out as mate and sailing master aboard The Deer, but due to the inadequacies of the captain Johnny was given the job of captaining the ship. He was promptly informed that what he believed was general merchandise in the hold, was in fact-munitions of war that were to be ferried to Texas to aid the Confederate cause. This didn’t discourage Johnny, and he dove into the task at hand with relish-“When I was let into the secret I was enthused rather than in any degree deterred from carrying out the expedition, and threw my whole heart into it.” Involved in conflicts from Haiti to Colombia, and from Mexico to Honduras, in many ways he was a rebel without a cause, that is, until he found his cause in the late 19th century Cuban War of Independence.


The final Cuban insurrection against the Spanish Crown was inspired and lead by José Martí. Martí is considered Cuba’s founding father. The similarities between José Martí’s revolution, and the Irish rebellion of 1916 are striking. Like Pádraig Pearse (the main instigator of the 1916 rebellion), José was both poet and revolutionary. Both men also envisioned a blood sacrifice and Martí’s words were as explicit as those of Pearse-“The reddest and slightest of poppies grows atop neglected graves. The tree that bears the sweetest fruit is the one with a dead man lying at its roots.”[5] [iii]

Martí (who died in one of the first skirmishes of the war) had been its guiding light and inspiration. He organised the planned rebellion from bases in New York and Florida, and his death was a major blow for the Cuban insurgents. Informants had plagued the Cuban struggle also, and many’s the expedition was scuttled by Spanish spies. With much success, the Spanish had taken to paying off ship captains to tell them where they intended to land. Once the rebels were ashore, the Spanish would emerge from their hiding place and kill each and every rebel.[iv]

The Cuban Junta, from their New York waterfront base, soon heard tell of Dynamite Johnny, and his previous filibustering exploits. Having tried their lot with many crooked captains, they put their trust in Johnny. Johnny, for his part, did not need to be asked twice and his first trip to aid the Cubans was soon underway, ferrying- “2500 rifles, a 12 pounder Hotchkiss field gun, 1500 revolvers, 200 short carbines. 1000 pounds of dynamite, 1200 machetes, an abundance of ammunition” and one-General Calixto Garcia-to the Island[v]. Dynamite Johnny’s first expedition was a roaring success, and soon Garcia was encamped in the mountains of Old Oriente Province, where, along with the guns Johnny had supplied, he vigourously engaged the Spanish forces. Johnny put in his lot with the Cubans, more out of sympathy with the Cuban cause than for any monetary gain involved. The Cubans were broke and, according to Johnny, there was more money to be made piloting legal cargo from New York-than ferrying armaments and men to Cuba. Of course, the attendant thrill of adventure must have also played a part in Johnny signing up for the job!

Johnny’s nemesis during the War was the head of Spanish Forces in Cuba-Valeriano “The Butcher” Weyler. Valeriano was mightily frustrated by Johnny’s expeditions. When Valeriano was asked his opinion on Johnny by a reporter, he gave it succinctly:“We will get him, and I will hang him from the flagpole of Cabaña Fortress.” When he heard of Valeriano’s declaration, Johnny replied through the same channels,“I will make a landing within plain sight of Havana on my next trip to Cuba. If we should capture you, which is much more likely than that you will ever capture me, I will have you chopped up into small pieces and fed to the fires of the Dauntless.” A few short months later, in May 1897, Johnny landed the Dauntless (and a large cargo of munitions) within three miles of the presidential palace (where Valeriano was sometime ensconced) and within one mile of Cabaña fortress.

The explosion of the U.S.S. Maine in Havana harbour indirectly led to Johnny’s retirement from filibustering. The sinking of that ship triggered the Spanish-American-Cuban War-thus negating the worth of Johnny’s job of ferrying illegal armaments to Cuba-those same cargos could now be ferried to their destination perfectly legally. Johnny always maintained that the explosion of the ship was most likely accidental, but the U.S. was convinced the Spanish were involved. Whoever perpetrated the action, or however it occurred, within six months, the Spanish-American War was over, and U.S. dominion now extended over the Philippines, Guam, Puerto Rico and other islands. Cuba was spared U.S. ownership because the Teller Amendment forbade such an action. The Teller amendment called for U.S. liberation of Cuba, not permanent occupation (perhaps due to the large Cuban communities in New York and Florida). More tellingly, Henry Teller (who proposed and drafted the Teller Amendment) was a Republican senator from Colorado, and he wanted to prevent Cuban sugar cane from competing with his own states sugar beet crop. His declaration read “we (the United States) hereby disclaim any disposition of intention to exercise sovereignty, jurisdiction, or control over said island except for pacification thereof, and asserts its determination, when that is accomplished, to leave the government and control of the island to its people.” Oh how history’s ball of yarn unravels and reason turns on a whimsical die! Follow the money, others might say. During the Spanish-American War the media had a huge part to play. In the American press, the war became an exotic (and often hyperbolic) drama. The most popular anecdotal story of the war in the U.S., relates the time when illustrator Fredric Remington cabled from a relatively peaceful Havana-"there will be no war." The supposed reply from his U.S. H.Q. came,"you furnish the pictures, I'll furnish the war." 

Theodore Roosevelt (who later became president) was promoted to Colonel when he arrived in Cuba. He jumped into the conflict with gusto, and captained the famed “Rough Riders” to victory at the decisive battle of San Juan, near Havana. The American Ambassador to Britain at the time, John Hay, when writing to Roosevelt after the hostilities had ended, famously declared the conflict to have been "a splendid little war." For Roosevelt (and many others) it added to U.S. territories abroad, galvanised the scattered factions of The Civil War into patriotism, and took the eyes of the U.S. media off domestic concerns. 

Photographic Portrait of Johnny, by Pirie MacDonald


Johnny found himself settling down at the age of 61. Perhaps he was tired of revolution and ruction? Or maybe there was no more rebellion to be had? The U.S’s Golden Eagle had now spread its wings firmly over the Americas, and Johnny would be hard pressed to find a theatre in which to play the game of war, without playing by the rules, and playing by the rules was something he was loath to do, “Any man that can’t disobey an order ain’t worth shucks.”[vi] Johnny was offered a position as chief Havana Harbour Pilot by the first president of Cuba-Thomas Estrada Palma. He took the job gladly, but a law was passed subsequently which made it compulsory for Cuban pilots to be Cuban citizens. Johnny could not be both a Cuban and an American citizen. He was on the point of resigning (as he would not renounce his American citizenship), but the Cuban’s waived the rule for him, and he continued the job with his pride restored, and his patriotism intact-becoming both a Cuban and American citizen.

On March 16th, 1912, Dynamite Johnny captained the resurrected warship "U.S.S. Maine" on its final journey to its proper burial three miles out from Havana Harbour. “The Maine” was raised from its watery grave in commemoration of those who went down with the ship and all those who had died in the insurrection. Johnny O’Brien was sole captain of the resurrected vessel and referred to it as “the proudest moment of my life”. The Maine was surrounded by a flotilla of 50 vessels and the entire population of Havana lined the city’s walls, as cannons fired minute guns in commemoration of those who had perished in the war. Imagine the scene: Johnny, dressed in his best morning suit, a starched white shirt and bow-tie, the sole crew member of the resurrected battleship, standing alone on deck, “a little black clad figure,”[vii] defying the huge vessel. From the warship’s masthead flies the stars and stripes, the “biggest and handsomest navy ensign”[viii] he has ever seen. A flotilla of 50 vessels circles the Maine, all thronged with sailors. Starboard of the ship is the great Cabaña fortress-ramparts lined with soldiers, cannons firing minute guns. To port-the old city of Havana-her whole population thronging the roofs and sea walls. Then, Johnny opens the valves in the bulkhead and the waters rush into the ship. He climbed down the ladder on March 16th, 1912, while concurrently in New York, 20,000 people marching in St. Patrick’s Day parade paused, and all the church bells rang for the war dead. Not once did Johnny look back at the sinking vessel, flinching neither to “God, chance nor the impatient hand of destiny.”[ix] Down went the Maine, slowly, smoothly, then the decks-exploding with the air pressure, hurtling masses of flowers which had been laid on its deck into the air, and the flag “Old Glory vanished under the foam with a flash of red white and blue as vivid as a flame.”[x] According to newspaper reports, before the Stars and Stripes sank beneath the waves, Johnny took it in his hand and kissed it.[xi]

As the twentieth century rolled in, and on, Johnny declared filibustering to be “in the dumps”.[xii] It seems, his like were the stuff of legend even before he died. The weary old filibuster travelled home from Cuba just before his death to see snowfall on New York’s Harbour once more before he died[xiii]. Johnny was once asked if he ever feared death, he replied, “I never feared that imminent deadly breach.” He passed over that breach on June 22nd, 1917, as the scorching New York summer rolled in. Dynamite Johnny died at Hotel America, 105 East Fifteenth Street, Manhattan. He was buried in Sailor’s Cemetery, City Island, with the Cuban government in charge of the services.[xiv] Johnny’s simple gravestone looks out onto the waters he sailed so often on. As the title of his ghost written autobiography states, he truly was, A Captain Unafraid.

[i]  A Captain Unafraid, 1912, Johnny’s ghost written autobiography by Horace Smith. Harper and Sons. Page 6.
[ii] A Captain Unafraid, 1912, page 10.
[iii] From the speech Pinos Nuevos by José Martí “La amapola más roja y más leve crece sobre las tumbas desatendidas. Él arbol que da mejor fruta es el que tiene debajo un muerto.”
[iv] A Captain Unafraid, 1912, page 77
[v] A Captain Unafraid, 1912, Page 80
[vi] Tugboat, The Moran Story by Eugene F. Reid and Louis Moran. Page 288
[vii] The Maine Sinks To Her Ocean Grave, New York Times article, date unknown.
[viii] The Spanish War, An American Epic by G.J.A. O Toole. Norton, 1984. Page 598.
[ix] The Spanish War, An American Epic. Page 400.[x] The Spanish War, An American Epic. Page 400.
[xi] Dynamite Johnny O’ Brien-Cuba’s American Hero, Marian Betancourt, article in Irish America Magazine, Dec/Jan 2003.
[xii] Memories of Two Wars, Fredrick Funston, 1911. Chapter 1: To Cuba as A Filibuster.
[xiii] New York Times, Dynamite Johnny O’ Brien’s obituary, June 22, 1917.
[xiv]Tugboat, The Moran Story, by Eugene F. Reid and Louis Moran. Page 291.

1. The dividing sections of the article are chapters from Johnny’s autobiography “A Captain Unafraid” ghost written by Horace Smith. 
2. The Masonic Standard, New York, Vol XVI, No 52, December 30, 1911, states that Johnny was 15 when he ran away from home. The article describes Johnny as a veteran of Masonry. Having been a member of Excelsior Lodge. No 195 since 1867. In “A Captain Unafraid,” Johnny says he was 13 when he absconded from home. 
3. Historian William F. Drake, in his book Little Phil (The Story of General Philip Henry Sheridan), maintains Philip was born at sea (thus not a U.S. born citizen) which precluded him from becoming president. Dynamite Johnny’s mother’s maiden name was Bridget Sheridan and she (according to Johnny’s autobiography “A Captain Unafraid”) was a relation of Philip Sheridan. “A Captain Unafraid” also states that both Johnny and Philip’s families emigrated together on the same boat.
4. Johnny’s first nickname was Daredevil Johnny.
5. This quote comes from a speech of Martí’s entitled Los Pinos Nuevos, in which Martí attempts to galvanize the spirit of his people for the fight to come; and perhaps to come to terms with his (and their) destined martydom on the altar of patriotism. It was given in Tampa in 1891-just a few short years before Martí died and his country was decimated by war.

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Tags: Cuba, Dynamite Johnny, Military History, United States, history

Comment by Charles G O' Brien on May 11, 2014 at 7:18pm

The second image in the blogpost is by A Captain Unafraid's illustrator - John O' Leary!

Comment by Ryan O'Rourke on May 16, 2014 at 5:04am

Excellent stuff, Charles.  Thanks for posting this.


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