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Teddy Roosevelt and the “Rough Riders” in Cuba

Aptly known as the “Rough Riders,” the 1st US Volunteer Cavalry Regiment came into being shortly after a mysterious explosion sunk the USS Maine in Havana Harbor on February 15, 1898. 

The 6,000-ton battleship had arrived in Cuba the month earlier ostensibly to protect American interests in the face of growing political and social unrest, though then Secretary of the Navy John Long asserted that its presence constituted nothing more than a “friendly visit.”

The source of the explosion that tore the ship apart and killed more than 250 officers and sailors has always been disputed and controversial, but the Navy’s official position was that it was caused by a Spanish mine, and as they say, the rest is history. 

Whatever the case, the incident propelled young Teddy Roosevelt and an eclectic band of volunteer soldiers into the national and international spotlights.  

The Call for Volunteers 

In the decades after the Civil War the American military was relatively small, unorganized, and underfunded, all of which made it particularly ill equipped for foreign entanglements.

However after the incident in Havana the public clamor for retribution reached a fevered pitch, and President William McKinley ordered his underlings to cobble together a mobile yet potent expeditionary force. 

Spurred on by the supposed attack on American sovereignty along with a deep seated desire to expel colonial Spanish forces from the small island nation less than 100 miles off Florida’s southernmost tip, the conditions were ripe for intervention as the growing independence rebellion continued to destabilize Cuba. 

The various forces would be led by Colonel Leonard Wood and former Assistant Secretary of the Navy and newly appointed Lieutenant Colonel Teddy Roosevelt – a staunch and vociferous proponent of Cuban independence.

Volunteers were originally to be recruited almost exclusively from the Arizona, New Mexico and Oklahoma Territories, largely because their hot inhospitable climates were similar to what the soldiers would experience in Cuba, and the response was so overwhelming that many otherwise fit and able men had to be turned away.  

In addition, at Roosevelt’s insistence, applicants from other parts of the country were also selected, and Rough Riders ultimately included eastern bluebloods, Union and Confederate Civil War Veterans and both Native and African Americans, though most were trappers, prospectors and mountain men from the rugged American Southwest. 

Though from widely varying backgrounds, all were skilled horsemen who refused to shy away from a good fight. 

Training and Equipment

The mass mobilization and transportation of thousands of men from all over the country led to the spread of multiple diseases and a stunningly high death rate in the early going. 

After arriving at the training facility in San Antonio, Texas, many men succumbed to the ravages of typhoid fever and tuberculosis. 

Nonetheless, since most of the recruits were already experienced horsemen, marksmen and outdoorsmen, their training focused on basic drills, protocol, and even the subtle nuances of military etiquette. 

Lieutenant Colonel Roosevelt used his political connections to ensure that his men were equipped at least as adequately as regular Army units, but their uniforms were decidedly more cowboy-ish.  

Including floppy felt hats, blue flannel shirts, heavy trousers, boots with gaiters and ochre handkerchiefs knotted around their necks, the Rough Riders were easy to distinguish from the regular soldiers they’d fight alongside, but their heavy garments would become annoyances and disadvantages in Cuba’s tropical jungles.   

In addition to bedrolls, tents, and gear for their horses and mules, the men were equipped with 5-shot, .30-caliber Model 1896 Carbines, Colt revolvers and Bowie knives, and their firepower increased drastically thanks to a last-minute gift from a wealthy supporter consisting of two tripod-mounted, 7 mm Mauser M1895 Colt–Browning machine guns.

Departure from the United States

Of the nearly 2,000 men who’d trained in Texas, nearly 20% died or were rendered unfit for duty thanks to the aforementioned illnesses.

By the time the healthy soldiers departed for Tampa many had lost close friends and morale was exceptionally low, but despite this unforeseen turn of events, in late May of 1898 more than 1,000 volunteers boarded Southern Pacific trains bound for South Florida. 

Due to logistical issues associated with their rushed departure however, many of their horses and pack mules were left behind. 

Hence, the cavalry men later facetiously referred to themselves as “Wood’s Weary Walkers,” because nearly all of their fighting in Cuba was done on foot. 

Upon arriving on Cuban soil on June 23, 1898, the men promptly unloaded their provisions, set up camp and waited patiently for orders. 

Battle of Las Guasimas

Having barely settled into camp life, the following day the Rough Riders were instructed to march to nearby Las Guasimas, but due to a lack of horses and pack mules, keeping everyone supplied and fed wasn’t easy.

Each soldier carried with him only enough rations and ammunition to last a few days, and since the Rough Riders weren’t accustomed to heavy marching like their cohorts in the infantry were, the humid conditions took a heavy toll.  

Advanced reconnaissance squads discovered a number of Spanish positions in and around Las Guasimas, and later that afternoon the Rough Riders marched to within a mile of the enemy, set up camp and made final preparations for the assault that would begin the following morning at first light.

The American side included the 1st Volunteer Cavalry, the 1st Regular Cavalry and the 10th Regular Cavalry made up of African American “Buffalo” soldiers, all of which were supported by artillery.

At Las Guasimas total strength was approximately 960 Americans and 600 pro-independence Cuban “rebels,” but Spanish forces were securely entrenched in hillside positions from which they enjoyed a number of distinct advantages over their attackers. 

First, the rugged terrain acted as a funnel allowing them to concentrate fire and other defensive efforts in a few localized areas, and in addition the Spanish had the high ground and were equipped with fast firing rifles and smokeless ammunition that didn’t reveal their positions with telltale puffs of white smoke.  

Just before General Young’s Army regulars attacked, artillery battalions began softening up enemy positions with 1.65-inch (41.9 mm) Hotchkiss mountain guns.  

Then starting the advance through the vine-choked thicket, many of the men found that the heat and terrain were even more debilitating than the enemy fire. 

Hungry, exhausted and dehydrated from the previous day’s march, many couldn’t keep up with the main force, and scores shed their shirts, dropped their bundles and collapsed where they were.

By some estimates, by the time the fighting reached its peak less than half the men who’d set out were actually in the action, but shortly after the assault began Teddy Roosevelt roused his Rough Riders and ordered them into two groups to support the regular’s flanks.

Together the combined forces pushed the Spanish back to their second line of defense, and by 9:30 AM they’d abandoned their positions altogether. 

During the roughly 90-minute battle the Rough Riders suffered eight dead and nearly three dozen wounded, but the lopsided victory set the stage for subsequent engagements.  

Battle of San Juan Hill

Fresh off success at Las Guasimas, on the first of July TR and the Rough Riders began marching the eight miles (13 km) to San Juan Hill, but again as was becoming maddeningly common, they had no specific orders other than to keep the 1,000+ Spanish soldiers there occupied.

It was thought that their mere presence would prevent the Spanish from retreating under the intense American artillery bombardment that was about to commence, while the main attack would come from Brigadier General Henry Lawton’s division against an even larger force at El Caney just a few miles away. 

Collectively, San Juan Hill, El Caney and others formed what was known as the San Juan Heights. 

When the artillery barrage began the volunteers found themselves dangerously close to the exploding shells, but instead of falling back they advanced up San Juan Hill, or Kettle Hill as it was often called.

Stopping within a few hundred yards of the Spanish positions, they cook cover among tall grass to avoid sniper and return artillery fire. 

Pinned down and in an increasingly worsening position, Roosevelt became irate at his superiors’ unwillingness to provide him with actionable orders.   

To rectify the situation he dispatched a number of messengers to the command post, and finally received word that he and his men were to continue the assault directly up the hill’s exposed face. 

Perched atop his trusty steed Texas, Roosevelt rallied the men to their feet, and though he later stated that he’d have preferred to be on the ground with them, his elevated position helped his voice carry farther and allowed the troops to see him over the dense foliage, but it also made him a prime target for snipers. 

Urging his men not to fall behind like some had done in the previous battle, he’s said to have drawn his sidearm and warned everyone that he’d fire on those who did.  

This apparently elicited a hearty chuckle from the Rough Riders, after which the assault began.  

As soldiers from various units began creeping up the hill amidst heavy fire, Roosevelt came to the conclusion that the “slow and steady” approach wouldn’t win the day in the face of overwhelming fire, and moments later he whipped the volunteers into a full-on charge. 

Though some regular Army units didn’t match their pace, others were stirred by the reckless if impressive show of bravado and joined in with equal enthusiasm. 

In a series of short rushes between which the units alternately stopped to provide cover fire, the soldiers stormed up Kettle Kill as cracks and muzzle flashes from Hotchkiss and Gatling guns erupted behind them. 

In an even more decisive victory than at Las Guasimas, Kettle Hill was taken in less than an hour, and shortly thereafter the whole of San Juan Heights had been wrested from the Spanish defenders. 

According to official records, of the nearly 500 men who charged up San Juan Hill, approximately 90 were killed or wounded, while six disappeared and were never seen again. 

Siege of Santiago

Located along Cuba’s far southeast coast, the port city of Santiago was the next step in liberating the island after the victories at Las Guasimas and San Juan Hill.

In fact, the primary objective of the larger Fifth Army Corps’ invasion had been the capture of Santiago de Cuba. 

As Spain’s last remaining stronghold, the harbor was chock full of heavy cruisers, hence taking it was key. 

With the city encircled and the situation becoming ever more dire, the Spanish Navy issued orders for the ships to leave port as American and Cuban forces closed the noose, ultimately pushing the remaining enemy troops into a relatively small central area. 

Just two days after the victory at San Juan Heights, the US Navy destroyed much of Spain’s vaunted Caribbean fleet including two destroyers and four armored cruisers. 

But though this catastrophic defeat was one of the final nails in the coffin of Spain’s once vast colonial empire, the Battle of Santiago de Cuba was still far from over. 

With the ship’s big guns silenced permanently and the last remaining troops running low on provisions and ammunition, the Rough Riders and Army regulars began a methodical door-to-door clearing of the city, while behind the scenes American and Spanish diplomats met to negotiate the inevitable surrender. 

By late July terms had been finalized and the remaining 9,000 Spanish soldiers laid down their arms.

Though on the surface Cuban independence was the agreement’s crown jewel, the United States acquired Guantanamo City and San Luis, as well as Puerto Rico, Guam and the Philippines. 

Ironically this unprecedented acquisition of foreign territory elevated the United States to the status of bonafide colonial power, which you may recall, leaders like McKinley and Roosevelt claimed to detest. 

In addition, the Spanish-American War marked the first time that the US intervened in a foreign conflict, a trend which – think Korea, Vietnam, Panama, Somalia, and Afghanistan – has lasted to the present day.

Return home

During their short stay in Cuba Rough Riders contracted everything from malaria and dysentery to yellow and typhoid fevers.  

Some died from their ailments, while the lucky ones were transported back to the United States aboard quarantine ships. 

The remaining Rough Riders came ashore at Montauk, New York in mid August and were met by their counterparts who’d been left stateside. 

Though those who hadn’t made the trip felt as if they’d let down their comrades and missed out on an epic adventure, Roosevelt famously stated that they’d done their duty no less than those who’d gone, fought and died. 

For the healthy volunteers a month-long celebration ensued, during which the group was presented with a number of unofficial mascots including a wild eagle from New Mexico and a mountain lion from Arizona. 

Then on September 15, the men were ordered to return their gear to the US federal government, to whom it actually belonged.  

Now jobless and without a war to fight, members of the 1st US Volunteer Cavalry disbanded, but not before Colonel Roosevelt commended their efforts, expressed his great pride at being one of them, and reminded them rather sullenly that there was little else to do but integrate back into society. 

Then the men bid one another adieu and headed back to their homes and families all over the country, but many found the transition to civilian life a difficult one. 

Previously held jobs had been filled, most of the ones that were available were mind numbingly boring, and due to sickness and injury some men were unfit for any meaningful work at all.

To make matters worse veterans benefits were almost nonexistent, and though a number of wealthy supporters donated funds to see the neediest volunteers through the trying time, many were too proud to take advantage of the largesse. 

After the war and a term as New York’s Governor, Theodore Roosevelt was chosen as President McKinley’s Vice Presidential running mate in his bid for a second term, and after his assassination in September of 1901, TR was sworn is as the youngest president in American history. 

Later on while writing his memoirs he described the Spanish-American War as a “splendid little war,” perhaps because his actions there largely helped rocket him to political stardom, and in addition the resounding victory over Spain solidified America’s place as an emerging world power with both imperial and interventionist aspirations.

In fact tTR regularly used his “bully pulpit” to shift America’s stance away from isolationism to actively and unabashedly protecting and promoting the country’s interests abroad. 

During his nearly two full terms in office, Roosevelt was among the Navy’s biggest proponents because he recognized this branch of the military for what it was – the proverbial “big stick” with which America could wield its growing might around the globe. 

Working with allies in Congress, Roosevelt increased the size, budget and efficiency of the Navy more rapidly than had ever been done in a similar timeframe. 

Despite their brief service, TR and the Rough Riders became timeless legends, thanks largely to Roosevelt’s own published accounts of their exploits.

All told, just more than 5,000 Americans died during the Spanish-American War, and for his actions on San Juan Hill Roosevelt earned a recommendation for the Congressional Medal of Honor. 

That said, the honor was ultimately denied, and according to legend TR didn’t take the news particularly well. 

Despite admirable service, the African American soldiers of the 10th Cavalry never received the notoriety that the Rough Riders did, though one of their commanding officers – Captain “Black Jack” Pershing who’d go on to lead American soldiers during World War I – was awarded the Silver Star. 

Outdoorsman, conservationist, president, family man and Rough Rider Theodore Roosevelt passed away from a pulmonary embolism at the age of 60 on January 6, 1919. 

Surprisingly the last Rough Rider, a man named Jesse Langdon, lived for another half century, and the surviving volunteers had annual reunions in Las Vegas until the mid-’60s, by which time their numbers had dwindled down to just a few men who were so aged and frail that they could no longer make the trip. 

In 1948 the US Post Office issued a commemorative stamp to honor the Rough Rider’s victories in Cuba, but ironically it didn’t feature a grinning, scarf and spectacle clad TR, but instead the likeness of a little known Captain named Owen O’Neill who was gunned down by Spanish Mausers while leading regular Army soldiers up San Juan Hill. 

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