San Juan

Dawn Of Empire, 1898: The US Invades Cuba

Dawn Of Empire, 1898: The US Invades Cuba

San Juan

It was hot.

Unlike their Spanish enemies, who were clothed in light leather shoes and cotton, American soldiers had come to the tropics in blue flannel shirts, heavy leather shoes, and brown woollen trousers.

Now Lt Col Roosevelt, Col Wood, and their First Volunteer Cavalry Regiment, the “Rough Riders”, were stalking through thick jungle in search of battle.

They needed to find the Spanish and beat them, quickly.

(For part one of this story, click left on 'Press Ganging Up On Spain: Newspapers, Politicians, And The Spanish-American War').

Cuban Jungle Hills
Cuban jungle hills (image: Anagoria)

It was late June, and the summer would soon bring an assortment of tropical diseases, the most common of which, described by Evan Thomas in The War Lovers, was yellow fever, or “the black vomit”:

“The mosquito-borne infection essentially melted soft tissues so that sufferers bled from the nose and gums, rectums and genitals, and vomited up something that looked roughly like coffee grounds but was actually stomach lining and intestine. Howling and ranting as they bled from every orifice, patients had to be tied down in bed so they would not splatter the infection around the wards”.

What wasn’t understood at the time was that it was the improper storage of rations that contributed to the 14 deaths from disease for every one from combat.

Hardtack, an unsalted baked flour biscuit, was dry and safe but boring and insufficient nutritionally.

It was supplemented with sugar, potatoes, salt and pepper, coffee, yeast, dried beans, and beef. The meat, of course, was the likely Achilles heel.

For their part, officers got better sanitation, at least on the boat ride over, and were thus theoretically less susceptible to disease.

Though, at 39, with middle age setting in, Roosevelt still had more chance of dying of yellow fever than he did of becoming a war hero, but that hadn’t stopped him coming.

Pugnacious and energetic, he personified better than anybody much of America at the time – it was restless, idealistic, and in search of a war. And having done as much as he could to bring one about, Roosevelt had since left the government to participate in it.

1800s America
Cowboys round up cattle in Colorado (image: Library of Congress)

A commission in the Rough Riders, meant to be a regiment of cowboys, had suited his independent, wild card personality – though, as it had turned out, Rough ‘Riders’ was a misnomer.

Limited transport ship space caused many of the men, and all of the horses (save the officers’) to be left behind.

Still, this “splendid set of men” had adjusted to life as infantry. Roosevelt described the south-westerners as: 

“…tall and sinewy, with resolute, weather-beaten faces, and eyes that looked a man straight in the face without flinching. They included in their ranks men of every occupation; but the three (most numerous) types were those of the cow-boy, the hunter, and the mining prospector… They were hardened to life in the open… Some of them came from the small frontier towns, but most were from the wilderness, having left their lonely hunters’ cabins and shifting cow-camps to seek new and more stirring adventures beyond the sea.”

In time, Roosevelt’s literary, political, and military adventures would make a legend of the Rough Riders, and turn him into a sort of American Winston Churchill. 

As it happened, Churchill himself was in Cuba in 1895 as a military observer with the Spanish.

It’s where he is said to have developed his taste for Cuban cigars.

He left in 1896, though not before having been sniped at by Cuban guerrillas.

Spanish snipers wait in the jungle (image from 'San Juan Hill 1898' by Angus Konstam © Osprey Publishing, part of Bloomsbury Publishing)

Now it was the Spanish who would do the sniping, while hiding in the depths of the jungle like the guerrillas they’d fought - the strategy was to delay as much as possible, so that disease could finish their numerically superior but less acclimatised opponents. 

In actual fact, they probably over-estimated the Americans’ ability to fight large-scale battles.

A lot had changed since the Civil War, and isolated postings at scattered outposts had become the norm – Rough Riders weren’t the only ones shaped by the frontier.

Although it looked intimidating, below the surface, the gears of the American military machine were creaking at the seams with having to supply and field an army that had rapidly swelled in the wake of war fever and the onrush of volunteers. 

Still, Spain’s problems were far worse, and they’d be the ones to truly struggle with fighting en mass again.

Soldiers in Cuba had been playing the anti-guerrilla game for so long, dispersing in small groups to root out freedom fighters, that regiments by this point existed as largely administrative bodies only.

A large social gulf between the over-supply of upper-crust junior officers and their ‘peasant’ men didn’t help matters. 

But at the outset, the numbers did at least look good for Spain on paper.

Governor Blanco had 160,000 troops in Cuba, while America would use the 20,000 men in its V Corps to do the main fighting there.

But the US had many other soldiers to hand, and although a lot would end up fighting in other Spanish colonies, Blanco didn’t know exactly how many American troops he’d face in Cuba, nor where they’d strike.

His men were thus spread out, and his force weakened. 

He hadn’t been wrong to hedge his bets. Havana, where the USS Maine had blown up – the literal flashpoint for relations with Spain, and America’s ostensible rationale for going to war – was the most obvious target.

But, when the US found out the core of the antiquated, dilapidated Spanish navy was at port in Santiago, they struck there. Seizure of Cuba’s second-largest city would be almost as fatal a blow as taking Havana, and the prospect of also sweeping up much of the enemy’s fleet in the dragnet was a temptation too good to resist.

Theatre of operations around Santiago (image from 'San Juan Hill 1898' by Angus Konstam © Osprey Publishing, part of Bloomsbury Publishing)

So the Americans had landed, unexpected and unopposed, 14 miles from Santiago at Daiquiri.

Amphibious operations are innately difficult, and some men did drown coming ashore, but the mere start of the war was in itself a moment of triumph for one of the men who’d accompanied them.

The newspaper tycoon William Randolph Hearst had championed the Cuban struggle for independence in his New York Journal, and had two of his men embedded with Roosevelt’s Rough Riders.

For one of them, Edward Marshall, it was no easy assignment.

“The oppressiveness of the heat,” Marshall recalled later, “made us gasp and sweat.”

As he slogged through the humidity, he heard a cuckoo.

Hadn’t there been reports that the Spanish used the birds as a warning signal?

His mind must have raced, while the soldiers around him talked about how much they wanted a cold beer, and their officers told them to keep quiet.  

Then it started – rifles cracked in the distance, and in an instant, bullets were zipping through the leaves. 

Two men dropped; Roosevelt flapped, stumbling forwards awkwardly with his sword caught between his legs.

Col Wood, “Old Icebox”, was true to his name, calm and collected, though privately he wished he’d taken out that $100,000 life insurance policy for his family.

Next, according to Thomas:

“Roosevelt was peering around a palm tree when a bullet thudded into the trunk, sending a cloud of dust and splinters into his ear and eye. In the span of three minutes nine of his men were hit.”

Probably not friendly fire then - but where were the damned shooters?

Just then, another reporter, who was right next to Roosevelt and would do much to elevate his reputation in the press, spotted the enemy.

He may have had sciatica so badly he could barely walk, but the square-jawed Richard Harding Davis had soldiered on enough to keep up, and would prove himself useful. 

“There they are, Colonel, look over there; I can see their hats near that glade,” he said to Roosevelt, pointing to a valley on the right.

Instantly, the Rough Riders showered the area with bullets, and the Spanish broke cover and ran over a nearby hill.

General Joe Wheeler, the commander of the cavalry and a veteran of the Confederacy was momentarily transported back to the Civil War.

“We’ve got the damn Yankees on the run!” he yelled.

As the larger Spanish force and the Americans bumped into each other, the Battle of Las Guasimas erupted, Rough Riders and ‘Buffalo’ soldiers in the 10 Regular Cavalry piling in.

The Battle of Las Guasimas (image: Library of Congress)

It was over quickly enough. The Spanish had soon been overwhelmed by superior numbers and fell back to the hills.

The difficulty was finding them.

The Spaniards were armed with a highly reliable 7mm five-shot bolt-action rifle, the 1893 Spanish Mauser, which used smokeless powder.

Ideally, the Americans were also equipped with the state-of-the art .3 inch (7.62mm) five-shot Krag-Jorgensen bolt-actions, or carbine variants for the cavalry.

These also used smokeless powder, but were less reliable than the Spanish side-arm - and in any case, shortages meant that many of the newer troops were given the obsolete Trapdoor Springfield Model 1873s.

Without smokeless powder, these advertised the firer’s position with a black cloud, though, thanks to Col Wood’s connections, he’d managed to avoid equipping his Rough Riders with these ‘contraptions’. 

But the Americans did have the social cohesion the Spanish lacked.

Although racist by today’s standards, Roosevelt and many with him were proud of the multi-cultural/international flare of their regiment, which included at least one Englishman and Australian, and even native Americans.

One Pawnee named Pollock is said to have joked about his own lineage before battle, turning to the regimental barber and asking: “Do you cut hair?”

The man answered: “Yes”; and Pollock continued, “Then you’d better cut mine…Don’t want to wear my hair long like a wild Indian when I’m in civilized warfare”.

Black troops’ conspicuous gallantry also inspired respect, despite the war providing a fight against a common enemy through which northern and southern troops, ranged against each other during the Civil War, could come back together.

The ‘Buffalo Soldiers’ caused at least some of their white comrades to question the Jim Crow segregation in the south and the ‘separate but equal’ principle (which was, in practice, anything but) handed down by the Supreme Court’s Plessy v. Ferguson decision in 1898. 

'Buffalo Soldiers' of the 25th Infantry at Fort Keogh, Montana, 1890 (image: Library of Congress)

Likewise, respect for Hispanic soldiers, both those they fought with and those they fought against, also increased in the coming months.

But racism still reared its ugly head.

The motley, irregular, and badly armed Cuban freedom fighters, for whom the war was ostensibly being fought, were thought of scornfully.

A Francis M McArty of the Rough Riders’ A Troop, said of them:

“Would I enlist again in case of further trouble in Cuba? No, I don’t think I would to fight the Spanish, but if I got a chance to go back to whip those dirty, thieving Cubans, who will neither fight nor work, I think that I would embrace the opportunity”.

Although they were on a high after the jungle skirmish, the Americans needn’t have been so confident.

The Spanish, not sure if this might be a diversion to draw them away from Santiago, had deliberately fought a running battle as they alternated engaging the enemy with falling back.

Trenches, barbed wire, and fortified buildings awaited the Americans in the hills outside the city, to which the Spaniards had now fled.

They certainly weren’t complacent – a mere 10,000 men were spread out between the city and the surrounding heights.

Their food supply was dwindling and the aqueduct (and thus water supply) threatened. They’d fight tooth and claw for every hill.

American infantry cut through barbed wire and charge towards El Caney (image from 'Harper's Pictorial History of the War with Spain' Vol 2)

The first was El Caney, a village in the heights turned into a fortress, from which a hail of Mauser bullets rained down on the Americans as they approached. One American participant described the battle thus:

“We can’t see them, and they are shooting us to pieces”.

One of those ‘shot to pieces’, and seriously wounded, was James Creelman, another of Hearst’s reporters:

“Opening my eyes, I saw Mr Hearst… a straw hat with a bright red ribbon on his head, a revolver at his belt, and a pencil and notebook in his hand.

"The man who had provoked the war had come to see the result with his own eyes and, finding one of his correspondents prostrate, was doing the work himself”.

According to Thomas, Hearst was “radiant with enthusiasm” as he interviewed Creelman about the “splendid fight” before rushing off to get the story to print.

Incredulous, Creelman later wrote in protest to his boss:

“After being abandoned without shelter or medicine and practically without food for nearly two days—most of the time under constant fire—you can judge my condition… That I am here and alive is due simply to my own efforts. I had to rise from my litter and stagger seven miles through the hills and mud without an attendant… I must get to the United States in order to get well. I expect no gratitude but I do expect a chance for my life”.

The Spanish suffered more – upon entering the fort at the centre of the village, after overwhelming and shooting down defenders at close range, the Americans found a horde of dead and wounded and floors wet with blood.

With Cuban guerrillas cutting them off, only 80 of the 520 soldiers defending the village made it back to Santiago when they were ordered to retreat.

But this was not down to any particular skill on the part of the attackers.

One British observer who witnessed the final attack on the village asked an American counterpart: “Is it customary with you to assault blockhouses and rifle pits before they have been searched (shelled) by artillery?” 

The truth is, the Americans were out of practice.

The determined Spanish defenders had not been beaten most efficiently, but rather by mass numbers.

Lack of experience, planning, reconnaissance, and poor logistical preparation meant that artillery was not maximally effective, and that when the obsolete black-powder emitting field guns did fire, they only had a limited ammunition supply with which to do so.

A country pathway within about 18 miles of San Juan Hill in southern Cuba

On a roll, the Americans plunged down narrow jungle trails towards the ultimate prize: San Juan Hill, the site of Spain’s main defence outside the city.

Yet here too, Spanish fire was intelligently employed on bottlenecks where the trails crossed streams. 

In 'San Juan Hill, 1898', Angus Konstam says that more than 400 men ended up as casualties as they were funnelled through one of these death zones - 'Bloody Ford' (the other was dubbed 'Hell's Pocket'). In his memoir 'The Little War of Private Post', Charles Johnson Post is even more explicit, giving a total of 709 casualties sustained whilst crossing through both these points, 85 of whom were killed.

As Konstam informs us, confusion and poor planning on the American side dogged this stage of the assault: 

“The signal Corps had inflated an observation balloon, and, tethered to a wagon, it accompanied the troops as they marched down the trail. It also served as a perfect range marker for the Spanish. ‘Huge, fat, yellow, quivering’, it drew heavy fire, and Maj Maxwell commanding the balloon detachment quickly became the most unpopular man in the army”.

It was eventually shot down, collapsing into a river near Lt John ‘Black Jack’ Pershing, an officer of the Buffalo Soldiers in the 10 Cavalry.

Map of San Juan Hill operations (image from 'San Juan Hill 1898' by Angus Konstam © Osprey Publishing, part of Bloomsbury Publishing)

He’d go on to command the American Expeditionary Force when the Zimmerman Telegram debacle brought the US into World War One.

Also there, by this point, was Roosevelt. Col Wood had been moved up to brigade command to replace a general who’d come down ill, and now Roosevelt was the sole commander of the Rough Riders. 

His 'crowded hour' would begin as a charge straight up Kettle Hill, a rise adjacent to San Juan that needed to be taken first.

With his men behind, and Buffalo soldiers on his flanks, Roosevelt rode his mount ahead of his men until it was wounded, at which point he continued the charge on foot. 

The Rough Riders on Kettle Hill by Mort Kunstler (image: The National Guard)

It was a rout. The small number of defenders ran straight for San Juan, leaving the Rough Riders and supporting troops crowding the top of the hill, where fire could be poured on San Juan just beyond.

Combined with Gattling-gun fire that raked the positions at the top for a full eight minutes, infantry were able to dash up the next slope. 

Roosevelt and the Rough Riders at the top of Kettle Hill (image by from 'Roosevelt's Rough Riders' by Alejandro de Quesada © Osprey Publishing, part of Bloomsbury Publishing)

When they reached the top, they discovered, to their pleasant surprise, that the Puerto Rican troops at the top had dug their trenches at the topographical, or absolute, top of the hill, meaning they’d created dead ground through which attacks could pass unmolested.

Digging trenches instead at the ‘military top’ a little further down, would have given them a clear view and field of fire over the entire hill.

The Puerto Ricans were soon overwhelmed.

To their left, Roosevelt had gained permission from superior officers to lead a second charge, and he cobbled together an assortment of cavalrymen from Kettle Hill that he then led up San Juan, on the right of the infantry.

Spanish soldiers next to the Puerto Ricans, only 200 of them in all, were soon facing, and overwhelmed by, 2,000 American cavalrymen (fighting on foot). 

Again, because of poorly dug and angled trenches, the Spanish defenders were unable to fire on the Americans for much of their advance up the slope, and a hurried exchange of fire took place at close range when the Americans got to the top.

Roosevelt fired back after being shot at by two Spaniards: 

“I closed in and fired twice, missing the first and killing the second (with my revolver)… Most of the fallen had little holes in their heads from which their brains were oozing.”

Trench fighting is what led the Spanish to suffer so many head wounds.

According to Alejandro de Quesada’s ‘Roosevelt’s Rough Riders’, the revolver was a special double-action Colt 1895.

His brother-in-law retrieved it for him from the Maine wreckage, and it was later engraved with “From the sunken battleship Maine” on one side, and “July 1st 1898, San Juan, carried and used by Col. Theodore Roosevelt” on the other.

The Rough Riders, victorious (image: Library of Congress)

In all, the Americans suffered 200 men killed and 1,100 wounded in the assaults on El Caney and San Juan, to the Spanish 215 killed and 375 wounded.

But as the Spanish had far fewer soldiers, 520 odd each at El Caney and San Juan - they’d lost more than half their force.

The Americans, despite their mistakes, had lost only a comparatively light 10 percent to death or wounds.

From there, Santiago itself was taken in the next two weeks. Admiral Cervera, encumbered as he was with bad ships, tried to make an heroic run out of the bay, but his tiny fleet was quickly surrounded, pummelled, and forced to surrender.

The Americans cheered him and his men for the bravery they displayed when they finally caught up with and took them prisoner. 

Victory had come quickly, but the Americans had still not missed the disease window.

4,000 men were hospitalised and Roosevelt used political pressure to have the army brought home.

Black and National Guard troops from the Deep South, thought to be less susceptible to tropical diseases, garrisoned the captured island in their stead while surrender terms could be worked out.

Spanish American War
Roosevelt (third from right, bottom row) and other officers who were cited for gallantry (image: Theodore Roosevelt Collection, Harvard College Library)

Terms were finally agreed to in December, 1898. According to Angus Konstam:

“(It was) an unmitigated disaster (for Spain). Apart from the loss of prestige, territory and lives, the war had another long-term impact. The army felt let down by the people and politicians… This, combined with industrial growth and political instability, helped sow the seeds for the Spanish Civil War (and fascism)”.

Conversely, while the US honoured Cuban independence, it was emboldened by victory, and added Puerto Rico, the Philippines, Saipan, and Guam to its territory.

It didn’t stop there:

“The Americans basked in their new position as a world power, and Hawaii and Panama were soon added to the list of overseas territories. The Spanish American War set a precedent for involvement in the Caribbean and the Pacific and set the American battle lines for war in the Pacific between 1941-5. American involvement in the Caribbean still continues today”.

A Republican campaign poster for 1900

Upon getting home, Roosevelt became Governor of New York, and soon found himself on McKinley’s re-election ticket as his vice-presidential running mate in the 1900 campaign. 

The war in Cuba was featured prominently on the campaign poster, with Cuba shown ‘liberated’ from oppressive Spanish rule, a partial counter to the Anti-Imperialist League’s arguments against America’s new overseas possessions.

In time though, their arguments would prove more relevant: dead American soldiers in the Philippines had genitals cut off and stuffed in their mouths, while live Filipinos were water-boarded.

The brutality empire brought with it engendered national soul searching.

"Well I hardly know which to take first!" A political cartoon shows Uncle Sam surveying a menu of possible colonies (image: Library of Congress)

Technically, of course, Cuba wasn’t really an imperial possession, but there too American corporate involvement would be a legacy of the 1898 war, and one that would contribute to instability, then revolution and communism. 

But that was in the future. Roosevelt had still managed to get his own ‘good war’ and it made a legend of him.

Not bad for a man who, as Naval Secretary, was in a better position than anybody else in the country to suspect that the USS Maine explosion was, in fact, the result of a coal fire igniting the magazine, and not a Spanish mine.

But this uncomfortable truth would have dampened the appetite for more warships and crippled naval expansion and empire.

And in any case, the committee investigating the blast hadn’t needed too much help to ignore Professor Alger, who Roosevelt had accused of ‘taking the Spanish side’ by suggesting a design flaw was actually to blame for the explosion.

The war would happen because Roosevelt, and enough other influential people, wanted it to.

When McKinley was assassinated by anarchist Leon Czolgosz in 1901, Roosevelt became president and would remain so until 1909.

The assassination of President McKinley (image: Library of Congress)

Hearst, who’d offered his yacht to the Navy and attempted to enlist, had been told to get a commission and missed his chance to fight.

As a mere ‘war correspondent’ his story wasn’t nearly as impressive as his rival Roosevelt’s, and when he also entered politics, he didn’t do nearly as well.  

Remaining outspoken throughout his life, he criticised American involvement in World War One, and, as a right-winger, Franklin Roosevelt’s New Deal.

But in later life, while near death in 1950, he worried that his papers were getting obsessed with communism. He cabled his editors:  


He died in 1951, unable to hold back the tide of McCarthyism. 

As president, Roosevelt turned out to be decidedly less bellicose than expected, instead ‘talking softly and carrying a big stick’.

But out of office, and with the advent of war in Europe, he slammed President Wilson for not getting involved, and then, when America did enter the war in 1917, he asked for a division to command.

When one wasn’t forthcoming, he told Wilson’s advisor Colonel House: “I’m only asking to die”.

House, who was by this point sick to death of Roosevelt’s meddling, retorted: “Oh? Did you make that point quite clear to the President?”

Hearst's reputation for yellow journalism used against him; and Roosevelt shown warning Europe to stay out of the Americas

Instead, his sons would see combat in World War One far more intense than anything he’d experienced in Cuba.

This was much to Roosevelt’s liking. He’d said he would rather see his own children die than grow up to be weaklings. 

In 1918, his youngest, Quentin, did just that, getting shot out of the sky while manoeuvring his plane, the axel of which was returned to the Roosevelts as a grim memento. It hung in the family home.

But it didn’t fulfil its purpose as proud monument, and, as he spent hours in the room trying to read, Roosevelt was consumed instead by sorrow, finally writing to his daughter-in-law that: “It is no use pretending that Quentin’s death is not terrible”.

A few months after the armistice, he suffered a blood clot in the night and died. One of his surviving sons wrote to another:


Click here for Part 1 of this story.

For more on the war in Cuba, read San Juan Hill 1898 by Angus Konstam. For information on the Rough Riders, read Roosevelt’s Rough Riders by Alejandro de Quesada. And for more military history, go to Osprey Publishing.

To get information on the politics surrounding the Spanish-American War, read The War Lovers: Roosevelt, Lodge, Hearst, and the Rush to Empire, 1898 by Evan Thomas.

By then ex-President Roosevelt shown in Allentown, Pennsylvania, in 1914