By Dave McCormick


As the Kentucky Regiment entered Quintayros Plaza a Spanish sentinel called out three challenges, hearing no response from the oncoming Kentucky militiamen, he fired his weapon. This alerted the 15 soldiers defending the jail to respond with a deadly barrage, that wounded a few of the Kentuckians, including their commanding officer, Colonel Theodore O’Hara, who suffered a wound to his thigh. The Kentucky Regiment known as the Kentucky Filibusters, was a diverse mix incorporating members from all social strata: unemployed laborers, tradesmen, store clerks, lawyers, and physicians. This was a group of hale and hearty Americans, not a ragtag bunch.

Of other fighting units, American and Cuban, the Kentuckians were the first to land on the shores of Cuba and performed as the van of the operation. They were the first to shed blood in in battle; their casualty rate represented one-third of the total casualty count. And these Kentuckians came close to altering the future of Cuba.


A Veteran of the Fourth Regiment, Kentucky Foot Volunteers, who served in the Mexican War, Lieutenant Colonel William Preston was approached Cristobal Mâdan, a pro-independence Cuban on the matter of a Cuban invasion. Preston was tapped to form a force of between two and four thousand soldiers ready to storm Cuban shores. When Preston declined, Madan approached Colonel John Williams, Preston’s regimental commander during the Mexican American War with the same proposition. Williams possessed the fighting credentials needed. As a member of a volunteer company from Clark County, Kentucky, he took part in both the assault on Veracruz and the fight at Cerro Gordo. Williams accepted Mandan’s proposal with one of his own; he would need $8 million to amass a force of 4,000 filibusters. On November 13, with the deal set Williams was named Major General of the proposed military corps. But this arrangement was short lived. With President Taylor’s staunch support of the 1818 Neutrality Act, Mandan informed Williams the invasion of Cuba was deferred until President Taylor left office in 1853. But within days General Narciso Lopez advanced the idea of his organization’s independent invasion strategy of its own.

Three Kentuckians, who had served as officers during the Mexican conflict in 1847, the earlier mentioned Colonel Theodore O’Hara, along with Colonel Pickett, and Major Hawkins, avowed their facilities and readiness to raise a contingent of Kentuckians to aid General Lopez in his efforts to see an independent Cuba or possibly a Cuba annexed by the United States. And what’s more these Kentucky gentlemen would foot the bill themselves. On February 28, 1850, Lopez’s second in command, General Ambrosio Jose Gonzalez, agreed to the proposal with O’Hara leading the van. More than 200 Kentuckians, and a number of Louisianans and Mississippians, equaled a total American force over 600 strong.

On March 12, writing from Elizabethtown, Kentucky, Colonel O’Hara contacted militia Captain William Hardy, directing him to “recruit a number of men to aid in revolutionizing the Island of Cuba.” Hardy, a former sergeant in Company B, Second Regiment, of the Kentucky Foot Volunteers, had seen the elephant during the assault on Veracruz where he suffered a wound to his face. Hardy’s was a tall order: “raise a contingent of five hundred men in northern Kentucky and southwestern Ohio; procure one hundred thousand dollars, one thousand muskets, five hundred uniforms, one hundred swords, and one hundred kegs of gunpowder.”

Hardy employed a creative deception in order to sidestep the Neutrality Act. Lecturing in Covington, he let it be known he was assembling a company to prospect for gold in California. Hardy let it be known that time was of the essence, as the party would soon quit Kentucky for New Orleans.

Although the Kentucky contingent was to fight alongside Cuba, Separatists’ nativism reared its ugly head as O’Hara directed Hardy: “We want the best quality of young, adventurous Americans. No Dutch or foreigners of any kind, and as many Kentuckians as possible. Men who can be relied on in all emergencies.”

At the same time, O’Hara guaranteed Hardy the rank of Major. Hardy’s brother, Richardson, joined the filibuster regiment as a lieutenant. Richardson would later write a 94-page narrative of the Cuban expedition entitled, The History and Adventures of the Cuban Expedition.

The volunteers of Kentucky filibuster Regiment were generally from the Blue Grass state’s northern counties: Jefferson, Shelby, Franklin, Scott, Boone, Kenton, and Campbell. These seven counties were interconnected via rough roadways that offered egress to the Ohio River port cities of Louisville and Covington.

Aside from Colonel Theodore O’Hara, Lieutenant Colonel John Thomas Pickett, Majors Thomas Theodore Hawkins and William Hardy, others rounded out the expedition’s officer corps; they included Adjutant Henry Theodore Titus, Quartermaster Thomas P. Hoy, Surgeon Dr. Samuel S. Scott, and Chaplain Reverend John McFarland McCann. In all, six companies made up the Kentucky Regiment. The six companies were all led by captains: John Allen of Shelbyville, Company A; W. T. Knight of Shelbyville, Company B; John Allen Logan of Shelbyville, Company C; Albert W. Johnson, of Scott County, Company D; Henry H. Robinson of Covington, Company E; and Fielding C. Wilson, of Louisville, Company F. Twenty lieutenants completed the Kentucky officers.

The steamer Martha Washington departed after dark on April 4, 1850, from Cincinnati, enroute for New Orleans. The Martha Washington set in at Covington, just long enough to board 50 Kentucky volunteers. Next stop Louisville, where about 40 filibusters from that area came aboard.

When the Martha Washington reached Evansville, Indiana, Major Hardy encountered Colonel O’Hara with his small Frankfort contingent aboard the steamer Saladin. Both ships steamed south. The Martha Washington reached Freeport, Louisiana, just three miles to the north of New Orleans on April 11th. The filibusters went ashore and secured lodgings. The following day the Saladin reached New Orleans, after setting in at Henderson, Kentucky, to pick up a pair of filibusters.

On April 13th with all the filibusters amassed at New Orleans, General Lopez convened with the filibuster officers to ensure all would be set for the invasion of Cuba. The April 14, 1850, edition of the New Orleans Picayune ran the following: “some sort of an expedition is about to start against Cuba,” But delays in sailing from New Orleans caused dissent among the Kentuckians. Most of the 200-plus Kentuckians marched in protest to St. Charles Hotel, the officers’ headquarters. The men simmered down upon Major Hardy’s word that they were leaving soon for California. A few disheartened Kentucky filibusters returned home. This seemed an odd statement, seeing that it was the talk of the town, and of several newspapers regarding the expedition to Cuba. At 9 p.m. on April 25th, the Kentucky filibusters left aboard the barque Georgiana under the loud huzzahs of well-wishers. During the darkness of 2 a.m. on the 26th, a fishing boat emerged beside the Georgiana. Climbing on board were Kentucky filibuster officers, Major Hawkins and Lieutenant Albert W. Johnson. Secreted aboard the Georgiana were 250 muskets along with ten thousand ball cartridges. It’s hard to fathom, that despite all the talk in New Orleans environs regarding an expedition to Cuba 17 filibusters who had fallen for Hardy’s ruse, of manning picks and shovels in the gold fields of California, not wielding muskets in Cuba, were not happy. Colonel O’Hara faced the complainants, “the expedition was going to Cuba to engage in a revolution.” Those loath to continue to Cuba could go back to New Orleans via the tug that would carry the Georgiana out to open waters. This proved a hallow statement because the tug moved on so swiftly after towing the Georgiana, that “no opportunity was given them to get on board the tug to return home.”

On May 14th the brigantine Susan Loud with 170 Louisiana Regiment filibusters, the Creole with the Mississippi Regiment of 170 men, and 20 or so tailings from Kentucky and Louisiana, and the Georgiana with well north of a 200-man Kentucky contingent, assembled on the leeward side of Contoy Island. It was while at Contoy that General Lôpez issued the following statement, those who “did not wish to go to Cuba could now have permission to return to the United States in the Georgiana.” The 17 who had balked had grown to 38 who boarded the Georgiana, but of that number only two were from Kentucky. Those returning home were treated to derogatory tongue-lashing by Captain W. T. Knight from the Creole’s deck.

The total contingent of filibusters now at about 610 (several newspapers erroneously reported the numbers well into the thousands) were packed aboard the Creole. An hour past midnight on May 17th, the vessel left the confines of Contoy Island for Cuba. There were things to be sorted; uniform shirts of red flannel, along with a black cloth cap with a lone-star cockade, were distributed among the volunteers. As the ship cut through the water under moonlight, weapons were distributed among the men. The 50 54-caliber “Mississippi” rifles, the best of the arms, went to the Kentucky riflemen. The Louisiana Regiment was armed with antiquated flint muskets, while all the officers were armed with sabers and equipped with the Jennings’ Patent Rifles, that fired lead cartridges at the staggering rate of 15 shells per minute. The majority of the enlistees fastened Bowie knives and pistols in their waist bands.

On May 19th once again, under the cover of 2 a.m. darkness, the Creole steamed into Cardenas Harbor. It had been slow sailing due to the poor quality of coal to feed the boilers. The filibusters were also vexed by a delay in going ashore; of all things this was due to too narrow of a plank that ate up over an hour of valuable time, for the entire 600-plus filibusters to alight from the Creole. Colonel O’Hara’s and his Kentucky Regiment were the first contingent ashore. The invasion was on! Lieutenant Colonel Pickett and two companies double timed the mile-and-a-half trek to railroad yard to secure the locomotives. This foray was followed by Colonel O’Hara, with the remaining four companies of Kentucky filibusters, under orders of General Lopez, to rush directly into town and seize the infantry barracks. This would prove a trying task. A mad scrambling ensued as O’Hara’s lack of direction had him marching his men in circles; that is until he ran into General Lopez who pointed out the way. O’Hara’s band had advanced two blocks towards the garrison’s barracks when “Halta! Qui vive! Que vive! was uttered by the aforementioned sentinel. O’Hara, replied, “Friends and Lopez.” Apparently not the response the Spanish sentinels wanted. This alerted the 15 Spanish soldiers to respond with a deadly barrage that let loose a violent volley with one of the rounds inflicting O’Hara’s wound to the thigh. With O’Hara down, Major Hawkins took over command of the Kentucky filibusters.

What followed was a flurry of action, so intense that it was impossible to give a clear account of the battle for Cardenas. Frenzied fighting with rifle, pistol, saber, and bowie knife, was going on, on all fronts: The center square, the Governor’s mansion, the army barracks, and from roofs of buildings on the plaza. The Spanish firing from barred windows exacted a toll on the filibusters, wounding several, and the whirling lancers on horseback, only heightened the chaos. The Spanish put up a fierce resistance. But by 8 a.m. the Spanish put down their weapons in surrender. A number of those who surrendered joined Lopez’s contingent, but the Cubans would not, as they feared a Spanish retaliation against such a small American force. The filibusters set up quarters in the plaza. As they had not rested and had nothing to eat in 24 hours; so, their main concern now was finding food and catching a catnap. But first it was time to bury the dead; the Kentucky Regiment reported eight, killed and wounded. That toll would rise.

But their repose was short lived. At 4 p.m. word arrived; Spanish soldiers braced with artillery were on their way to Cardenas. Fearing the enemies’ larger numbers, General Lopez thought it best to remove his men to the Vuelta Abajo region of western Pinar del Rio. There “he would find a force organized and ready to support him.” Lopez informed Major Hawkins of the large Spanish force advancing on Cardenas and gave orders for the Kentuckians remain in Cardenas’s Quintayros Plaza to serve as a rear guard. But there was no time for that. The Spanish had already arrived and had skulked into the Plaza unnoticed. They opened a barrage of deadly gunfire. John McCann, the Kentucky Chaplain suffered a wound to the chest. But that was not the worst of it; the Spaniards fell upon McCann with bayonets and lances. Enraged, Captain Albert Johnson ordered “fire” and Johnson noted, “all five [Spaniards] fell upon the body of McCann….” At another area of the Plaza, a contingent Spanish Lancers charged the Kentucky filibusters, and fired into their lines. At a gallop, they drove into Captain Logan’s Company. Logan caught the brunt of the onslaught. He was “terrible mangled” being “shot through the calves of both legs” and was transported by his men to the Creole. Less than half the number of lancers that charged Logan’s position, managed to reach Captain Allen’s company. Seven were killed and their commander paid dearly, “riddled with more than fifty balls.”

It was a trying day for the filibusters, suffering 26 killed along with another 60 wounded. The Kentucky contingent lost an additional three officers and five enlistees and suffered another 19 wounded. Logan moved from the wounded legions, adding a number to the fatality’s column, as he passed away at midnight. Hours later “his remains were sowed up in a blanket, with 30 pounds of lead at the foot, and consigned to the Florida Straits.”

Heading home in defeat, the Creole found itself in a cat-andmouse game on the 21st of June, with the Spanish warship, the Pizarro. The filibusters arrived at Key West, just 100 yards out front of the Pizarro.

There was a lot of blame to go around for the failure of the Cuban Expedition. One of the Kentuckians voiced that “the fatal error [was] landing at Cardenas, instead or going to Mantua in the first place…” Colonel O’Hara faulted, “the fatal consequence of an indiscriminate enlistment or men,” especially the “riffraff ” and “blackguard rowdies” who joined the Louisiana Regiment. Cristobal Madan queried how O’Hara “embarked in a movement having only Gen. Lopez for a leader,” rather than a more capable American officer. But in the end, none of that speculation mattered. On June 30, 1850, the expedition leaders were indicted for violating the Neutrality Act. Of the Kentuckians, O’Hara, Pickett, and Hawkins were charged for their actions. Brought to trial in New Orleans three times, produced three hung juries. The Federal Government gave up and dropped the charges.

Had the expedition proved successful the men were to receive the same pay as they would if serving in the U.S. Army. At the end of one year, or at the success of the expedition, the men would receive $4,000 USD, or the same value of land in Cuba. Hardy explained these high inducements were offered, due to the level of danger involved. But, Howard Jones, in his work Crucible of Power: A History of American Foreign Relations to 1913, takes issue with those numbers. He states the rewards were $1,000 and 160 acres of land and all [the filibusters] could pillage.

* * *

© 2025 By Dave McCormick

With a master’s degree in Regional Planning from the University of Massachusetts David McCormick was employed by the City of Springfield, Massachusetts, for several years. Now retired he works as a freelance writer; his articles have appeared in Army Magazine, Michigan History, Naval History, and Pennsylvania Heritage, among others.

* Views expressed by contributors are their own and do not necessarily represent those of MilitaryHistoryOnline.com.