A filibuster today brings to mind U.S. senators stalling legislation. But the filibusters of yesteryear referred to a different sort of disruptor, also known as a freebooter, and those active in the New River territory dealt in international intrigue. One of them was Napolean Bonaparte Broward, who would later become Florida’s governor.
Americans who supported Cuba’s independence from Spain were running guns or lending their vessels to the cause. At the time, our future governor was one of three owners of a speedy oceangoing tug named the Three Friends.
The tug’s fearless captain, “Dynamite Johnny” O’Brien, got his name from a voyage he helmed transporting 60 tons of dynamite to Colombia. The captain faced a hurricane, a hysterical crew and an electrical storm, but he prevailed, according to historian Stuart McIver.
McIver’s research reveals that in May 1897, the sternwheeler Biscayne, cruising somewhere along the New River, was loaded with guns and ammunition destined for Cuba. (Sternwheelers were steamboats driven by a single paddlewheel at the stern.)
At a position further downriver, this cargo was to be downloaded onto the cutter Dauntless. That was captained by none other than Broward’s notorious tugmaster, Dynamite Johnny O’Brien.
Meanwhile, a special agent from the Treasury Department named Benjamin Hambleton was vacationing here and sailing near the New River inlet. He spotted the Biscayne in waters normally too rough for a sternwheeler.
When the waters calmed, the Biscayne docked alongside the Dauntless for the transfer of the armaments. But the spying Hambleton bore down on them, hopping into his rowboat and shouting, “In the name of the law, I command you to stop putting those arms on that vessel. You are all under arrest.” Hambleton scrambled aboard with his shotgun but was unceremoniously disarmed and tossed back into his rowboat.
Meanwhile, another U.S. vessel, the Marblehead (one of just a few ships that could outpace the Dauntless) happened onto the scene and interrupted the loading. Dynamite Johnny and the Dauntless sped off.
All this as a war was brewing.
Two years before the New River incident, Cuban nationalists inspired by Jose Marti began a campaign against Spanish rule. Many Americans sympathized – not only with the Cubans’ right to self-rule but also with an eye on the sugar trade. The “Cuba Libre” movement even established offices in Florida and held fundraising events across the U.S.
The effort grew as Spanish and Cuban military leaders grew more brutal.
Our newspapers had a field day, drumming up calls for U.S. intervention. President Grover Cleveland resisted, and so did his successor, President William McKinley. McKinley, however, began military preparations. Teddy Roosevelt was then serving as Secretary of the Navy and was an aggressive supporter of war with Spain.
In January 1898, the U.S. Navy sent the USS Maine to the Havana harbor to protect American citizens on the island. A month later, a mysterious explosion sunk the cruiser and killed all 266 aboard. While there was no proof of a culprit, an outcry ensued and the U.S. immediately set up a blockade of Cuba.
Spain, the country that once controlled all of Florida, declared war on the U.S. and the U.S. reciprocated. Thus began the Spanish-American War, which resulted not only in Spain’s defeat in Cuba, but also in its colonies around the world including the Philippines, Puerto Rico and Guam.
And Dynamite Johnny and the Dauntless? After a six-hour chase, the Marblehead caught up to them.
Since the unloading operation had been interrupted back on the New River, cargo was still piled on the docks. A U.S. lieutenant approached one of the men there amidst the rifles wrapped in burlap and boxes clearly marked “.43 caliber.” The U.S. officer pointed to a box of cartridges and asked one of the boatmen held there, “What are these, sardines?”
Clearly, these officials had little interest in prosecuting the gunrunners.
And the Dauntless crew? Days after they were apprehended at sea, they appeared before a Key West court, where they were freed “due to a lack of evidence.”
In less than two weeks, Dynamite Johnny and the Dauntless “filibusters” were back in business.








