Skip to main content

“The Gray-Eyed Man of Destiny”

July 2024
14min read

The daring epic of the filibusters reached a lurid climax when little William Walker captured the sovereign state of Nicaragua

For a young American who wanted excitement and adventure along with a chance to get rich quick, the United States of a hundred years ago offered plentiful opportunity. The adjustment of the Oregon boundary with Great Britain in 1846, the decisive victory over Mexico and the acquisition of about half the territory of that unfortunate republic in 1848, and then, almost immediately afterward, the discovery of gold in California—all these opened avenues of adventure tor men of mettle and daring.

There was, as well, lor the truly reckless or the desperate, an even more alluring outlet than settling new lands or prospecting for gold, and this had the promise that the gold they were after had already been mined. The men who followed this highly dangerous way were called filibusters—a term used then in its most masculine sense, meaning freebooters, and not, as now, windy and obstructive politicians. These exuberant daredevils tried to seize by force of arms various Latin American countries, usually with the sincere belief that they were the instruments of the “Manifest Destiny” of the United States to acquire and civili/e the chaotic and wartorn republics to the south.

The extremists of this imperialistic faith fervently believed that the United States, following its destiny, would eventually annex the entire Western Hemisphere from the Arctic snows to Cape Horn. And in 1856 they came very close indeed to success in Nicaragua, when William Walker made himself president of that harassed republic, the only time in history a native-born American has become the head of another sovereign nation. If Walker had then acted with discretion the whole history of the Americas might have been changed, for he and most of the other rampaging filibusters were proslavery southerners whose enthusiasm for American expansion was linked with the desire to gain new lands for that “peculiar institution.”

The times favored a spirit of enthusiastic nationalism and an unshakable conviction of the superiority of the United States over all other nations. Few Americans then cared what the rest of the world thought of them—what they thought ol the rest of the world was all that mattered. Even the federal government caught the fever of expansion; the Administration of President Franklin Pierce (1853–57) approached Russia about the purchase of Alaska, broached the matter of annexation with the king of the Hawaiian Islands, attempted to buy Cuba from Spain, and made overtures toward the purchase of a large naval base in the Dominican Republic. None ot these efforts succeeded at the time, however, and the only tangible gain of territory was the land acquired along the Mexican border by the Gadsden Purchase of 1853.

Most of the filibusters, who sought to gain by force what their government could not acquire by diplomacy, were men of the frontier with a good leavening of Mississippi River men of the “hall-horse-hall-alligator” type. There was a certain proportion ot barflies and drifters from the slums of the big cities, but the officers and hard core of these adventurers must have been a magnificent lot of men, the pick of the frontiersmen of the time. An English explorer wrote of some of William Walker’s followers in Nicaragua: “Tall, upright, broadshouldered men they were nearly all. Their heads were well set on, hands and feet small, muscles like iron … the very pick of the Western States—men highly thought of even there for reckless daring. … They were simply the most good-natured, goodtempered fellows I ever met with.”


The filibusters used two general methods of operation. The first was a slainbang landing on the coast of one of the southern republics and the proclamation of a new government with the invaders holding all the key offices. But this forthright procedure was so blatantly crude and smacked so of piracy that it outraged public opinion not only in the country attacked but throughout the world; it never gained more than the initial local success of surprise.

The more successful method was for a group of Americans to enlist as a distinct corps in one of the warring factions in the new Spanish-speaking republics. For a while these volunteers were eagerly sought by the revolutionary leaders because of their superb fighting qualities; they were recruited by promises of sizable tracts of land—the idea being that these soldiers of fortune, after victory was attained, would settle down as solid citizens to enjoy the rewards of victory. The danger, however, was that these adventurers, as a compact and disciplined body, would seize the government itself. This is exactly what William Walker and his loi lowers accomplished in Nicaragua, in the RIibuster which came nearest to permanent success.

Walker’s filibustering career had begun two years before—with a fiasco. In the autumn of 1853 he had descended with forty-odd followers on Lower California and proclaimed it an independent republic with himself as president. When reinforcements arrived he extended his sway on paper by a proclamation annexing the neighboring state of Sonora to his newly established nation ami the San Francisco newspaper Alta California aptly noted, “It would have been just as cheap and easy to have annexed the whole of Mexico at once, and would have saved the trouble of making future proclamations.” The whole affair was ridiculouns on ihe surface but not so funny to some of the people immediately in Walker’s way, for he had a deadly determination and never hesitated to execute anyone who obstructed his purpose. Chased out of Lower California, he managed to lead 33 surviving followers back to safety across the border below San Diego on May 8, 1854, which happened to be his thirtieth birthday.

But from this initial defeat Walker was to go on to become the grand master of the filibusters. One would imagine that the leader of such hard-bitten daredevils must have been a man of splendid physique and overwhelming personality. But Walker was nothing of the sort. He was about as innocuous looking as a man could be. Only about five feet, five inches in height, he weighed just over a hundred pounds. Mis hair and eyebrows were tow-white and his pale lace was covered with the freckles which usually go with such coloring. His expression was heavy and lie was taciturn to an extreme, but when lie spoke he gained attention with the first word uttered. His eyes were his striking features: all noticed their piercing gray coldness and he became known as “the gray-eyed man of destiny.”

Born in Nashville, Tennessee, in 1824 of ScotchIrish ancestry, Walker had studied medicine in Europe but turned to the law in Nashville and New Orleans upon his return. Then lie became a journalist and moved to California, where he edited a newspaper in San Francisco, but later he practiced law again in Marysville until in October, 1853, he sailed with followers from Sun Francisco for his invasion of Lower California.


His first humiliating failure in that expedition taught Walker a lew lessons but in no way cured him of the filibustering lever. In 1855 he was off again, this time to Nicaragua. There, instead of making a rash and forthright landing, he gained entry as the leader of a band of soldier-colonists who were to serve under the banner of the Outs (who happened to be the Liberals) in the current revolution. His followers became citizens of the country by a simple declaration of intention and were promised grants of land when their newly adopted cause 1IVOn victory.

In Nicaragua Walker found a green and fertile land whose fragrant orange groves, sparkling lakes, and smoking volcanoes had so tarried away an early English monk that he had called it “Mahomet’s Paradise.” The little country had achieved a shaky independence alter the downfall of the Mexican emperor in iS^sj, but ever since had been kept in turmoil by civil warla re. Nicaragua had a special importance for Americans, in these years between the Gold Rush and the Golden Spike, because through it ran the favored route to California—a relatively comfortable passage from one ocean to the other by river and lake boat and a short stretch of road.

Walker’s first move was to gain control of this Transit route, which would give him his vital supply line for recruits and equipment from the United States. On a sunny June morning he assembled his little army outside ihe Legitimist (i.e., Conservative) stronghold of Rivas, which controlled the road section of the Transit route, ‘and about noon he led them on a reckless frontal charge into the town.

At the first shots, his native allies turned tail and left the fifty-odd Americans to fight ten times their numbers. The invaders met a steady and deadly fire as they charged toward the central plaza with wild yells and cheers (the usual head-on tactics of filibusters) and were soon forced to take shelter in several adobe houses where they were surrounded by the enemy. The Legitimists then set fire to the shelterin houses and an immediate retreat became imperative to save the survivors. The Americans sallied forth with cheers and shouts and, before the enemy could meet this unexpected offensive, pushed through the streets to the outskirts of the town. Several of the wounded were too seriously hurt to move, and these were immediately butchered by the Legitimists and their bodies burned. The enemy losses, however, were ten times those of the Americans, and thereafter no sober natives ever wanted to shoot it out at close range with the gringos.

It was a badly beaten group of survivors who reassembled in a cacao plantation outside the town. But Walker got them safely back to their base and in August led them on another foray against the enemy force, which, though ten times as large, had consumed so much brandy to rouse their courage before the battle that the Americans won an easy victory. Walker now decided on the one really brilliant stroke of generalship in his career. The entire Legitimist army was at Rivas, leaving Granada, the government seat, undefended. Walker loaded his entire force, now increased to 350 by recruits from the United States and native volunteers, on the Transit Line’s steamer, sailed them up Lake Nicaragua and advanced at night on the unsuspecting city. They surged over an unmanned barricade and rushed at the double into the main plaza, encountering only a few scattered shots from the skeleton garrison, who then turned and fled. In a matter of hours, with the loss of one soldier, Walker was master of the enemy capital.

By his capture of Granada, Walker put himself in a position which might very possibly have led in time to his dominance of all Central America and even, just possibly, to the eventual conquest of Cuba as well, and its consolidation into a Central American-Caribbean empire of sorts, which, based on slavery, would be a firm ally of the southern states. It was a stirring prospect and the chances are that Walker dimly glimpsed its glitter. His failings, however, were a stubborn refusal to heed the advice of experienced advisers and an overwhelming impatience, the occupational disease of almost all dictators. And these faults betrayed him.

For a while, however, he played his newly won trumps with considerable skill. First, he released about a hundred political prisoners rotting in chains and dungeons under Granada’s great cathedral. The day after the capture of the city he attended Mass at the cathedral, accompanied by many of his officers, and soon won the powerful support of the clergy by his respect for church property and traditions. Two weeks later the Legitimist commander acknowledged defeat and came into Granada to arrange a peace. Walker put on a great show for his entry by lining the streets and the plaza with his heavily armed followers and also armed and paraded a large number of male travelers stranded in the city because of the closure of the Transit route.

The result was a treaty which ended hostilities and named Patricio Rivas, an innocuous Legitimist, temporary president of the united republic. It appointed William Walker as commander in chief of the combined armies. The Legitimist garrison at Fort San Carlos and another farther down the San Juan River then abandoned their posts, and the Transit Line was again open to free movement. Landing with 58 men, William Walker had, in effect, captured Nicaragua in a little more than four months.

But only a few months later, in February, 1856, war broke out with Nicaragua’s southern neighbor, the republic of Costa Rica, which raised an army of 9,000 men and declared war on Walker’s “bandits.” To compound his difficulties, Walker rashly decided to seize the steamers and properties of the Transit Company. Commodore Cornelius Vanderbilt had built up this line and had given, at first, every aid and assistance to Walker, who, he hoped, would bring peace and order to the revolution-wracked country. But Walker, whose knowledge of warfare in the financial jungle was limited, chose to line up with a faction seeking to oust Vanderbilt from control.

The old Commodore’s wrath, when he heard of the confiscation, was said to have been terrible beyond description. He not only suspended the sailing of all Transit ships to Nicaragua, thus cutting Walker’s supply line, but began intriguing both with the Costa Ricans and with Walker’s puppet, President Rivas. Shortly after the Costa Rican army crossed the border, President Rivas went into revolt and appealed for help to the three little countries to the north—Guatemala, El Salvador, and Honduras. Walker met this crisis by assuming formal control of the government. On July 12, 1856, with a grand parade through the main square of Granada, he took the oath of office as president of Nicaragua. The American minister to Nicaragua, John H. Wheeler, a friend of Walker’s, rashly took it upon himself to recognize the new government, but when the news reached Washington, Secretary of State Marcy recalled Wheeler and forced his resignation.

Some of Walker’s proclamations, during the months between his formal accession to power and his downfall, were drastic. He confiscated many of the natives’ estates to raise money, placed English on an equal legal basis with Spanish, and made changes in the land laws with the frank purpose of placing “a large portion of the land of the country in the hands of the white race”—meaning his own followers. Most potentially fateful was his decree relegalizing slavery, which had been abolished thirty years before. The significance of this decree was that Walker, rebuffed in his diplomatic overtures to the government at Washington, was casting his lot with the southern states in the impending Civil War. There is reason to believe that some of the southern leaders shared Walker’s dream of a Latin American slave union as an ally in their own struggle.

None of these decrees ever went into effect because Walker’s time was running out. By October he was under attack from the south by the Costa Ricans, and from the north by the combined armies of Guatemala, El Salvador, and Honduras. In this crisis Walker decided to evacuate Granada and to move his headquarters to the volcanic island of Ometepe on Lake Nicaragua. In order to deny his enemies the prestige of a conquest, he left his second in command, Charles Frederick Henningsen, a British soldier of fortune, at Granada with orders to destroy the city utterly.

Henningsen organized his men into demolition detachments and systematically began to blow up and burn the buildings section by section, while the hysterical natives streamed out of the city. Henningsen’s men naturally found loot and wines and spirits in most of the houses they entered. Henningsen was unable to restrain his officers and they, in turn, lost all control of their men. As nightfall came, the city became an obscenity with flames shooting skyward, clouds of smoke hugging the roof tops, and groups of howling drunk, smoke-blackened filibusters screaming and reeling through the streets in an orgy of plunder and destruction. For two days and two nights this bedlam of annihilation rose to a crescendo as the crazed Americans drank and plundered, smashed and fired buildings, fell in a drunken stupor from which they would be awakened, likely as not, by the kicks of yelling and singing comrades, to rise dizzily and stagger on to smash and fire other buildings in the raging inferno of explosions and smoke—and to drink some more.

The enemy forces presently attacked the city from three different sides and one column seized the Guadalupe church, which stood on the street running between the wharf on Lake Nicaragua and the main plaza where Henningsen was rallying his men.

After setting fire to all the surrounding buildings, he began to fight his way, foot by foot, down the street toward the wharf. At first, many of the Americans were still half drunk, and some took to the bottle again in the face of such imminent danger. Somehow Henningsen finally got them sober and into a kind of order. A filibuster named Calvin O’Neal, whose brother had fallen in the first onslaughts, came to Henningsen in a frenzy of raging grief and asked permission to charge a body of 400 or 500 Guatemalan soldiers who could be seen forming in the distance. His commander gave him 32 picked Rifles. What followed was later described by Walker:

“O’Neal, barefooted and in his shirt sleeves, leaped on his horse, and calling on his Rifles to follow, dashed into the midst of the allies as they formed near the old church. The men, fired by the spirit of their leader, followed in the same fierce career, dealing death and destruction on the terrified foe. The allies were entirely unprepared for O’Neal’s sudden, clashing charge, and they fell as heedless travellers before the blast of the simoom. The slaughter made by the thirty-two Rifles was fearful, and so far were O’Neal and his men carried by the ‘rapture of the strife’ that it was difficult for Henningsen to recall them to the Plaza. When they did return it was through streets almost blocked with the bodies of the Guatemalans they had slain.”

By the next morning Henningsen had concentrated his forces in the main plaza and could count his strength. He had lost 23 men killed or captured and could muster only 227 soldiers fit for duty; he was burdened with 73 wounded and some 70 women and children and sick.

Two days later, on November 27, after blowing up a church on the plaza and destroying the nearby buildings (Henningsen was still carrying out his orders amidst the inferno), he poured a heavy artillery fire into the Guadalupe church and captured it by an immediately following assault by 60 picked Rifles. At once he moved all his forces and supplies into this large, strong building and prepared to withstand a siege until Walker could relieve him from the lake. His men had recovered from their debauchery and were willing to work and fight for their lives and for the protection of all the noncombatants. But the crowded and unsanitary conditions in the church, the food of mule and horse meat, the night chills and rains, and the stench from the unburied enemy dead outside brought much sickness to the 400 Americans huddled together, and cholera soon appeared as a far more dreadful foe than the enemy.

A ministering angel appeared amidst these terrible scenes, Mrs. Edward Bingham, the wife of an invalid actor who had brought his family to Nicaragua to take up one of Walker’s grants of land to American settlers. From the time of her arrival she had nursed in the American hospitals, and in the Guadalupe church she constantly tended the sick and wounded with magnificent courage and complete self-sacrifice which gained her the deepest gratitude of all the soldiers. Finally, worn out and weak, she became another victim of the dreaded cholera and died within a few hours. Her children perished with her, but her invalid husband survived all the horrors of the siege and eventually reached California safely. Of all the Americans in Nicaragua this splendid woman showed the finest spirit.

For two harrowing weeks Henningsen held out while Walker stood off Granada in the lake steamer Virgen, watching for a chance to extricate Henningsen’s forces. Then, during the first week in December, 300 recruits arrived from New Orleans and San Francisco, well-equipped men in fine fettle and spoiling for a fight. Of these, 160 were organized as a relief force and placed under the command of the cavalry leader, Colonel John Waters. Waters landed his men and silently led them toward the city. By dawn he had stormed over all the enemy, barricades and had joined Henningsen, with a loss of about a fourth of his men. The Americans, who had been slowly extending their lines from the Guadalupe church down the street toward the water, quickly seized the wharf and embarked the survivors on the Virgen without enemy opposition.


General Henningsen, before he boarded the rescuing steamer, cast one last look back at the ruined city. Then he thrust a lance into the ground and to it attached a piece of rawhide upon which he had written, Aqui fué Granada —“Here was Granada.”

Walker was not licked yet. He still commanded 900 men and controlled the Transit route, over which he expected several hundred reinforcements. But his enemies included, along with four sovereign states, the redoubtable Commodore Vanderbilt. Early in the autumn of 1856 the Commodore had dispatched to Costa Rica a young secret agent named Sylvanus Spencer with a well-planned scheme to seize the Transit route and bottle up the filibusters. With a small Costa Rican force and a boldness worthy of Walker himself, Spencer swooped down on one of Walker’s garrisons, seized the river steamers, and cut off the filibuster reinforcements. By April, 1857, Walker’s force was trapped at Rivas, with no hope of escape. By arrangement with the Central American armies he surrendered to an American naval officer, Commander Charles H. Davis, and was spirited off to New Orleans, where he received a hero’s welcome.

Three more times William Walker and his followers attempted to invade Nicaragua without success. On the last attempt Walker surrendered to a British naval officer, who turned him over to the Honduran authorities, from whom he received short shrift. On September 12, 1860, he met his death before an adobe wall at the hands of a firing squad, an end which he had decreed so often for his political enemies. He was buried in an unmarked grave which Joaquin Miller commemorated in his poem “That Night in Nicaragua.” Despite his ruthlessness and unappealing personality, Walker held the constant loyalty of many of his followers through all his later failures and, surprisingly enough, that of many of the natives as well. His men were beyond description daring. His able lieutenant, General Henningsen, years later wrote a fitting epitaph for these Homeric men of Nicaragua:

“I was on the Confederate side in many of the bloodiest battles of the late war; but I aver that if, at the end of that war, I had been allowed to pick five thousand of the bravest Confederate or Federal soldiers I ever saw, and could resurrect and pit against them one thousand of such men as lie beneath the orange trees of Nicaragua, I feel certain that the thousand would have scattered and utterly routed the five thousand within an hour. All military science failed, on a suddenly given field, before assailants who came on at run, to close with their revolvers, and who thought little of charging a battery, pistol in hand. …

“Such men do not turn up in the average of everyday life, nor do I ever expect to see their like again.”

Enjoy our work? Help us keep going.

Now in its 75th year, American Heritage relies on contributions from readers like you to survive. You can support this magazine of trusted historical writing and the volunteers that sustain it by donating today.