Dynamite Johnny O’Brien – East River Pilot and International Arms Smuggler

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I was reading the Brooklyn Eagle’s August 25, 1943 edition in the archive when I came across the fascinating story of  “Dynamite” Johnny O’Brien who was the most famous gunrunner of his generation and a hero not only in Cuba, but in much of Latin America. The article was written by a man called Heffernan who spoke about his recollections of Greenpoint.  One of his recollections was that O’Brien often drank in a bar on Greenpoint Avenue was  and the captain also often used to moor his three masted schooner in Newtown Creek.  I cannot prove that O’Brien ever lived in Greenpoint, but he certainly spent a good bit of time there. It is very likely his brother Peter lived here.

Like many other nautical  people who later settled in Greenpoint, Johnny O’Brien was born on April 20, 1837 near the East River in what was called “The Dry Dock” section of Manhattan . His parents were farmers from County Longford, but in New York O’Brien’s father worked as a machinist at the East River shipyards. O’Brien was related to the famous Civil War Cavalry General Phil Sheridan. The O’Brien and Sheridan families even came to this country on the same ship

“My childhood playground,” O’Brien often said, “was the neighboring shipyards,” where he learned to spin oakum and wedge treenails into boats. He also  learned to sail and navigate on his older brother Peter’s ferry– then merely  a large rowboat with a sail – crossing the East River to Greenpoint. His brother would later work for years as  one of the pilots on the Greenpoint ferry,but Johnnie was so intoxicated with the sea that his parents finally let him leave home at 13 to sign on as a cook on a fishing sloop. He eventually piloted fishing and sailing yachts, served as apprentice on the pilot boat Jane, and spent time on a Union ship during the Civil War.

It was, however, during the Civil War that Johnny discovered his greatest passion- gun running, or as it was known then, fillibustering. Although he had been in the Union Navy, Johnny evidently was a sailor on board a ship that carried rebel guns to Mexico where they were later  smuggled back to the south.

“Being constitutionally disposed to giving orders rather than obeying them,” O’Brien took the required navigation training for a command rank as a pilot in the Hell Gate Pilots Association, forerunner of today’s Sandy Hook Pilots Association. He earned the nickname “Daredevil Johnny”  because of the chances he took, he nevertheless he  always got through the then treacherous currents between the East River and Long Island Sound without mishap.

Johnny was already almost fifty years old when he began to sail as a filibuster to Latin America. In 1885 he made several voyages to help the Colombian rebels. He soon was assisting rebels in Honduras with supplies of weapons too. O’Brien was a short man with a thick gray handlebar mustache and the proud stance of a buccaneer. But there was no bravado about him, a New York Tribune reporter wrote. “He is one of the most daring and clear-headed that ever lived, a man with a hair trigger intelligence that enabled him to act as swiftly as he could think.”

He soon became involved with Cubanos who were trying to liberate their country from Spanish Imperialism. The work was very dangerous because he could have been arrested by United States customs agents or by the Navy since there were laws that prohibited sending weapons to the Cuba. Spanish authorities would have summarily shot him had they ever caught him.

It was in 1888 that he earned his nickname.  A wealthy Cubano had purchased sixty tons of explosives and the yacht the Rambler, but needed a captain to sail it to Cuba. In those days people did not know how to denature dynamite for travel so that traveling with it was highly risky, especially on the seas.  a fearful storm full of lightning hit the ship and boxes of  the dynamite got loose from their  moorings and began to slide around the hold. Had they hit one another they would have exploded and sunk the ship. The storm was shaking the ship so violently that there was danger that anyone who went below to secure the boxes might be hit by the large cases and suffer harm. The crew was so frightened by the prospect of entering the hold that they refused. O’Brien entered the hold and managed to secure the violently tossing boxes of dynamite. He not only fastened the cases in the hold but also earned his famous moniker.

Working for the Cubans was dangerous for another reason. The movement was also riddled with spies and agents who would betray the rebels. Spain had an elaborate ring of spies who followed the Cuban rebels. Many ships were run aground by traitorous pilots who were paid by the Spanish who were waiting on the shore. The rebels were executed on the spot by the Spaniards who had set the traps.  The Cuban rebels had obtained a ship called the Bermuda, but unbeknownst to them one of the pilots was a traitor who had agreed to take the ship into a cove where Spanish vessels lay waiting to pounce on the rebel ship. Johnny had navigated the ship into Cuban waters when he gave the wheel of the ship over to the double-crossing pilot. Johnny was suspicious and quickly realized that he was being betrayed. He grabbed the pilot and threw him off the bridge before quickly righting the vessel. The pilot was shot and thrown overboard.  One of the rebels on board was the Cuban general Garcia who said, ” We will never forget you. YOu have kept your word where our own have betrayed us. ” All in all Dynamite Johnny made about forty successful trips to Cuba and he became so infamous that the Spanish offered him a bribe large enough to make him a rich man if he had given up gun running. O’ Brien refused the offer and became sympathetic to the Cuban rebels.

One reason why Johnny was able to evade the Spaniards so often is that their ships were slower, however, one time he chanced upon a Spanish steamer that was faster than his craft and there was no way to outrun her. There was panic on the part of the Cubans on the ship because they could not outrun the Spanish war ship, which was mounted with guns capable of sinking O’Brien’s unarmed ship. Dynamite Johnny was absolutely cool and level-headed in this dangerous situation and he realized that part of the cargo was a piece of field artillery destined for land combat, but not meant to be fired from a ship at sea. Simply firing the gun could blow up O’Brien’s vessel, which was loaded with boxes of highly volatile nitro. Nevertheless it was the crew’s only chance, even though firing the gun and hitting the Spanish ship seemed like a miracle. The crew quickly assembled the gun and lashed it to the bulwark of the ship and one of the Americans who was aiding the Cubans had been a gunner’s mate on the battleship Maine. When they pulled the cord to fire the gun nothing happened and terror gripped the ship,but the next time the gun did fire and they hit the pilot’s house of the Spanish ship ending the chase.

As O’Brien told the story, his repeated success  so angered Captain-General Weyler, then the ruler of the island, that he sent a message to the daring filibuster, through an American newspaper man, somewhat as follows: “Tell O’Brien that we will get him, sooner or later, and when we do, instead of having him shot along with his Cuban companions, I am going to have him ignominiously hanged from the flag-pole at Cabana, in full view of the city.” Cabana is the old fortress across the bay, visible from nearly all parts of Havana. To this, O’Brien sent reply saying: “To show my contempt for you and all who take orders from you, I will make a landing within plain sight of Havana on my next trip to Cuba. I may even land an expedition inside of the harbor and take you away a prisoner. 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 months later, this little Irishman, whom Weyler denounced as a “bloodthirsty, dare-devil,” and who may have been a dare-devil but was not bloodthirsty, actually carried out a part of this seemingly reckless threat. He landed a cargo within a mile and a half of Morro Castle. In May, 1897, two carloads of arms and ammunition were shipped from New York to Jacksonville where they were eventually transferred first to a tugboat and eventually to O’Brien’s ship the dauntless right under the noses of Federal Customs agents. Off Palm Beach, General Nunez and some sixty Cubans were taken from a fishing boat, according to a prearranged plan. The Captain landed most of the Cuban passengers and the weapons under the very guns, such as they were, of Morro Castle, and within about three miles of the Palace of Captain-General Weyler. All that time, a force of insurgents under Rodriguez and Aurenguren was operating in that immediate vicinity, and was in great need of the supplies thus obtained. Some of the dynamite O’Brien landed was used the next day to blow up a train on which Weyler was supposed to be travelling, but in their haste the Cubans got one train ahead of that carrying the official party. The row that Weyler made about this landing was probably never  forgotten by the subordinates who were the immediate victims of his rage.

After Cuban independence the newly independent government offered him a position as head pilot in Havana harbor if he would become a Cuban citizen. O’Brien did not want to become a citizen of Cuba and got the job anyway.  One of his jobs was taking the remnants of the battleship Maine, which had blown up in Havana harbor, and bringing them out to sea where they were sunk. O’Brien was the last man to set foot on the Maine.

At the end of his life O’Brien wanted to return to New York and see one last winter.  He died in 1917 at the age of eighty. I read that an Irishman is making a documentary film about his life. He has a facebook page.


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