The Rough Riders

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The Rough Riders

Towards the end of the nineteenth century, William McKinley defeated
Grover Cleveland for the presidency and there was a huge push for the
United States of America to expand beyond its continental boarders.

(Lorant, p. 281) With an enthusiasm for a new urge for international
Manifest Destiny, the American people wanted to match Europe^s imperial
power by making America^s weight felt around the world. (Boger p.714)

The extent of expansionism was felt in the Pacific Ocean with the
occupation of the Hawaiian Islands and Guam, but the most famous
example of Americas enthusiasm for international assertiveness came in
the Caribbean with the war for Cuban independence against Spain. (Boger
p.714) The Spanish-American war was a war that made the United States
emerge as a world power and has sense been thought of as the most
popular war in American history. (Lorant, p. 281) As John Hay had
said, ^It has been a splendid little war, begun with the highest
matters, carried on with mag! nificent intelligence and spirit,
favored by the fortune which loves the brave.^ (Lorant, p. 297) Words
that truly captured the feelings of all Americans at the time. In the
American people^s eyes, the war was not won by political jargon or a
decisive Naval campaign, but by a rugged Lieutenant Colonel and his
band of outlaws, cowboys, and Harvard polo-players, more commonly known
as the Rough Riders. (Lorant, p. 295) Although the war was not won by
Roosevelt^s Rough Rider charge up San Juan Hill, the battle gave the
war its romantic essence, which still fills history books today.

Roosevelt^s Rough Riders were a key part in the fight for Cuban
Independence by brave yet unconventional means that made them one of
the most popular fighting forces in American history.

Soon after McKinley^s presidential victory in 1896, he appointed
Theodore Roosevelt to the office of Assistant Secretary of the Navy
under John D. Long. (Lorant, p. 281) The main problems of the time
were the occupation of Cuba by Spain and the fact that relations with
Spain were steadily worsening. American sympathy was with the Cubans
who were rebelling against the corrupt and evil Spanish overlords.

(Lorant, p. 281) Americans attitude towards the Cuban people was
mainly on humanitarian motives, but other reasons came into play to
push the United States into a fight. The first reason was being
economic. (Lorant, p. 281) The trade with Cuba, which had been one
hundred million dollars in 1893, was badly disrupted by the
insurrection. (Lorant, p. 281) Another reason was geo-political.

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United States had always wanted to control the Caribbean area, with all
it^s islands and opportunities. The United States badly needed ports
for it^s growing Navy and the United States!
wanted to protect the approaches to the present site of the Isthmain
canal linking the Atlantic and Pacific oceans. (Lorant, p. 281) As if
the fire needed anymore fuel, Joseph Pulitzer^s New York World and
William Randolph Hearst^s New York Journal continually published a
series of Cuban atrocity stories which told of the inhumanities of the
Spanish government, lead by the Spanish commander, General Weyler, who
herded non-combatant Cubans into concentration camps where 200,000
Cubans died. (Lorant, p. 282) More reports kept following in about
rapes, robbery, and unspeakable crimes. Although the American people
wanted to act, McKinley, and Cleveland before him, wanted to remain
neutral. Roosevelt disagreed with the decision and was convinced the
United States should fight for the independence and civil liberties of
Cuba. (Lorant, p. 282) Roosevelt was constantly trying to persuade
others, including McKinley, into listening to his beliefs on the
matter of war and was alway! s trying to bring the Navy to full
strength. Roosevelt felt that diplomacy is ^utterly useless,^ without
force behind it and that, ^the diplomat is the servant, not the master
of the soldier.^ (Lorant, p. 282) But more often than not, Roosevelt
was over stepping his boundaries and McKinley was set on giving Spain
the opportunity to reform their ways. Reform would not come in enough
time. Several events determined the destiny of Spain. The first was
being a letter intercepted in February of 1898 by a Cuban revolutionary
agent and turned over to the New York Journal. (Lorant, p. 282) The
letter was from Enrique de Lome, the Spanish Minister in Washington,
and stated that President McKinley was ^weak and a bidder for the
administration of the crowd, besides being a would-be politician who
tries to leave a door behind himself while keeping on good terms with
the jingoes in the party.^ (Lorant, p. 282) This infuriated the
American people, believing that Spain was taunting the United States,
not to mention the complete lack of respect for the President. Spain^s
arrogance was a complete slap in the face as far as Roosevelt and the
American people were concerned. Still, McKinley rema! ined unmoved by
the letter and remained neutral about Spain. The next chain of events
would prove to be disastrous for Spain. The U.S.S. Maine while at
anchor on a ^peaceful^ mission in Havana harbor, Cuba, was blown-up and
sank with the loss of two hundred and sixty lives. (Lorant, p. 283)

The explosion was thought to be either set by the Spanish, Cuban
provocateurs or an internal explosion on the ship, but the American
people were thoroughly convinced the Spanish government was responsible
for this horrible act of terrorism. Still Roosevelt argued intensely
for war but McKinley waited for terms for change. Without proper
authority, Roosevelt cabled Commodore Dewey, the head of the American
Naval forces, to hold the Spanish fleet on the Philippine islands and
to be prepared for war by keeping plenty of munitions and coal aboard
his vessels. (Lorant, p. 282) Then, After a long investigation in
Cuba, a Spanish underwater mine was determined to be the cause of the
explosio! n of the U.S.S. Maine. (It was later determined that an
inner coal fire was the cause of the explosion.) With the report of
the underwater mine racing across the country, on April 11 1898,
President McKinley delivered his War speech to Congress. (Lorant, p.
282) With ^Remember the Maine^ on the lips of all Americans, the
country prepared for battle, including an elated Theodore Roosevelt.
(Grantham, p. 51) Roosevelt immediately resigned his post as Assistant
Secretary of the Navy, ordered a new uniform from Brooks Brothers, half
a dozen pair of spectacles, some horses and was off to join a brand new
volunteer regiment in Texas. (Lorant, p. 282)

Although friends warned Roosevelt that to resign his post in the Navy
Department might mean the end of his political career, he ignored the
warnings because he felt he needed to prove himself in battle. (Lorant,
p. 295) Congress had authorized the recruitment of three volunteer
cavalry regiments in the United States and territories of the West and
Southwest. . (Lorant, p. 295) General Russell A. Alger, the Secretary
of War, was ready to place Roosevelt as the head of one of the
regiments, but Roosevelt declined the offer and proposed that his
friend Leonard Wood, a young Army surgeon, should be given the
command. Roosevelt settled for the rank of Lieutenant Colonel. .
(Lorant, p. 295) After several names were labeled to fit the new
regiment, the Rough Riders, as it was came to be known, was formed and
became one of the most extraordinary fighting forces ever to be
assembled in the United States military. . (Lorant, p. 295) The Rough
Riders was made up of hard riding cowbo! ys, iron-tough gamblers,
native Americans, and recruits whose relations with the law were
strained at best. On the other side of the spectrum, from the East
came adventurous college boys from Harvard, polo-players, and Long
Island fox hunters. . (Lorant, p. 298) The Rough Riders were a motley
and undisciplined regiment but was physically tough and were excellent
shots and horsemen. Most of all and especially to Roosevelt^s liking,
they were eager to fight. Colonel Wood had joked, ^ If we don^t get
them to Cuba quickly to fight Spaniards there is a great danger that
they^ll be fighting one another.^ (Jeffers, p. 170) They trained all
day long starting at 5:50 am and ending at 9:00 p.m., with constant
mounted and ground drilling to instill the discipline of military
life. They wore their blue shirts, loosely knotted handkerchiefs
around their necks, brown pants, and leggings, boots and
slouched-brimmed hats that quickly became the regiments trademark. The
rifles they carr! ied were regular army carbines and they were also
issued army revolvers. Sabers, the traditional symbol of the cavalry
were not issued because of their ineffectiveness in battle. (Jeffers,
p. 175) The men quickly grew used to the life of a cavalry soldier.

^Above all,^ Roosevelt wrote in his book The Rough Riders, ^every man
felt, and had constantly instilled into him, a keen pride of the
regiment, and a resolute purpose to do his whole duty uncomplainingly,
and, above all, to win glory the way he handled himself in battle.^
(Jeffers, p. 177) The term Rough Rider did not sit well with the
soldiers in the beginning. They did not want people to think they were
some kind of sideshow. They wanted to be known as a ^ regiment that
may be of rough riders, but they will be as orderly, obedient, and
generally well disciplined a body as any equal number of men in any
bunch of the service.^ (Jeffers, p. 151) The reason why the Rough
Riders were such good soldiers was largely due t! o the fact that they
counted the cost before entering the regiment. (Grantham, p. 51) All
members of the Rough Riders were prepared for their own deaths and the
death of their enemy. (Jeffers, p. 154) The Rough Riders had become a
full military regiment and had the pride to match any in the regular

While the Rough Riders were training in San Antonio, Texas, Commodore
Dewey won the first victory in the war in the Philippines. (Lorant, p.
283) One of the main reasons for this decisive victory was due to the
state of readiness he had assumed on Roosevelt^s orders while Assistant
Secretary of the Navy. Dewey sailed from Hong Kong with his squadron
and on the night of April 30, he slipped into Manilla Bay, where the
Spanish fleet lay at anchor. At dawn he closed into range before
giving his famous order of, ^You may fire when ready, Gridley.^
(Lorant, p. 295) Five times he passed the Spanish fleet, raking it with
heavy gunfire. The Spanish fleet was successfully destroyed.

Now it was time for the ground troops to make their way to Cuba for the
land war. Lack of transportation and horrible accommodations made the
journey from Key West, Flordia very difficult and uneasy for men who
were mostly used to being on open pastures, not open waters. (Lorant,
p. 296) The vessels allowed standing room only because of the capacity
of the ships were stretched to twice the expected limit. (Lorant, p.
296) Upon the arrival of Cuba, ruff seas and lack of sufficient docks
caused many of the boats to capsize, resulting in the loss of
ammunition, rifles and food. The ruff seas also took the lives of two
Rough Riders coming ashore in the choppy waters. (Jeffers, p. 209)
The conditions on shore did not get any better. Heat and humidity
along with strange surroundings caused for an unsettling setting for a
war. While landing, they were not met by any of the expected
resistance in the town of Daiquiri because the Spaniards fled after
being bombarded with shell! s from the war ships in the harbor.
(Jeffers, p. 209) They were met by a group of four hundred Cuban
insurgents who were brandishing rifles from several periods of history,
and proved only to be useful as scouts for the army. (Jeffers, p. 209)
Another problem that arose was the fact that the Rough Riders were a
mounted cavalry but on their way to Cuba there was no room for the
horses. The Rough Riders soon became known by the regular army troops
as ^Wood^s Weary Walkers.^ (Jeffers, p. 210) Even with all the
difficulties that had arisen, the Rough Riders were still ready to

Their mission was to push towards the main town of Santiago were the
main concentration of Spanish soldiers had been stationed. (Jeffers, p.
215) Two days after their arrival in Cuba, while advancing through
thick jungle in the mountains at Las Guansimas, the Rough Riders were
introduced to their ^baptism of fire.^ (Lorant, p.296) Although the
skirmish was brief, Richard Davis, a news correspondent who accompanied
the regiment, said the skirmish was ^the hottest, hastiest fight I ever
imagined.^ (Jeffers, p. 215) Sixteen Rough Riders lost their lives and
another fifty were wounded. (Jeffers, p. 215) As the men were being
wounded they continued to fight. One of the soldiers who was mortally
wounded through the hip, asked for his canteen and his rifle and
continued to fight until he died. (Jeffers, p. 220) This was a common
occurrence and showed the strong personal fortitude of the Rough
Riders. The battle was considered a victory, which was the first for
the Rough Riders ! and an embarrassment for the regular army brass
that produced little effectiveness. (Grantham, p. 51) They set camp in
the small town called Sevilla of Las Guansiamas. There was little food
and other supplies which Roosevelt considered this a failure of the
Army Commisionary Department as one more evidence of the nations
unprepardness for war. (Jeffers, p. 222) But despite all the problems,
Roosevelt wrote, ^From the generals to the privates, all were eager to
march against Santiago.^ (Jeffers, p. 223) After a long look of
Santiago, the commanders decided to take the trenches on San Juan Hill
in order to have the high ground advantage over the town and the fort
of El Caney. On July 1st and 2nd, at San Juan Hill, the Rough Riders
would endure their greatest test with the capture of the Spanish
entrenchment at the summit of the hill.

As the troops set up at the foot of San Juan Hill, the United States
artillery forces opened fire on the Spanish troops guarding the hill.
The Spanish quickly returned fire and the exact strength and position
of the enemy was not known. The troops had become pinned down at the
foot of the hill by a heavy barrage of artillery fire. (Jeffers, p.
223) While the men hid behind whatever they could find for protection,
Roosevelt sat upon his horse ^Texas^ with his revolver drawn (which he
given by his brother-in-law from the sunken Maine), shouting and riding
among his men so they would be ready for the charge. He wore a dark
blue shirt, with yellow suspenders with silver fasteners. (Jeffers, p.
230) He was determined to set an example of courage, but he also set a
tempting yet elusive target for the Spanish^s German Mauser rifles. As
Roosevelt and the other commanders waited for a signal to start the
upward charge, men all around were being picked off by the Spanish.
With gr! eat frustration, Roosevelt sent messenger after messenger to
find a general to give the forward charge command. He was finally
given the welcomed command to move forward and support the regular army
troops hesitated to advance because of confusion in the orders. So
Roosevelt led his Rough Riders up the hill in front of everyone else.

With the 9th regiment in front, the 1st on the left and the 3rd, 6th,
and 10th behind, the troops soon saw the Lieutenant Colonel charging up
the hill with his regiment following loyally behind and joined in the
gallant charge. (Jeffers, p. 232) The regiments soon became
intermingled with Roosevelt spear heading the charge in what he called
^my crowded hour.^ (Jeffers, p. 234) From all sides the troops were
overpowering the Spanish lines. Roosevelt managed to kill two
Spaniards on his way up the summit. The Rough Riders, the 9th and
scattered members of the 1st cavalry scrambled up the hill. Roosevelt
breathlessly reached the top and almos! t immediately the Rough Riders
and the 9th swarmed around him. The Rough Riders, along with other
members of the regular and volunteer troops, had successfully taken San
Juan Hill but American history would assign the glory to only one man,
Theodore Roosevelt. (Jeffers, p. 237) But their glory was shot lived.

Immediately, the Spanish troops started firing and shooting cannons at
the men on top of San Juan Hill and the rest of the regular army troops
battling to reach the summit. (Jeffers, p. 237) Roosevelt immediately
led a heavy charge of all the troops, both regulars and volunteer
straight into the fire in the trenches to give coverage for the
advancing men. White and black soldiers became intermixed during the
attack but advancing as one causing the Spaniards to flee or
surrender. Roosevelt had fragments of six cavalry regiments under his
command. Finally, the regiments took over the trenches and managed to
capture food and supplies. They found shovels, trenching too! ls,
picks, coffee, and food found still hot on the stoves. (Jeffers, p.

Out of the four hundred and ninety Rough Riders who had marched into
the battle for San Juan Heights, eighty nine had been killed or
wounded, the heaviest loss suffered by any regiment in the cavalry
division. (Jeffers, p. 241) Roosevelt attributed the heavy losses to
the fact that his men had done the charging. That the Rough Riders had
suffered more heavily than their opponents was a point of pride for
Roosevelt. Everyone who had witnessed both charges on San Juan Hill
and the trenches agreed that they had occurred only because of the man
who had led them. Roosevelt was highly regarded by everyone fighting
against the Spanish, which was made known by a recommendation sent to
secretary of War Alger that Roosevelt be awarded the Congressional
Medal of Honor, which is the highest honor awarded to a soldier, and
was signed by Colonel LeonardWood. (Jeffers, p. 243) Great admiration
had also been directed toward the Rough Rider regiment received a new
Official name, the 11th United States Horse. (Jeffers, p. 248) But
no one admired the Rough Riders more than the man who trained and led
them into their place in history. Roosevelt proudly wrote, ^ In less
than sixty days the regiment had been raised, organize, equipped,
drilled, mounted, dismounted, kept for a fortnight on transports and
put through two victorious aggressive fights in very difficult country,
the loss in killed and wounded amounting to a quarter of those
engaged. This is a record, which is not easy to match in the history
of the volunteer organization^. It may be doubted whether there was
any regiment which made such a record during the first months of any of
out wars.^ (Jeffers, p. 248) Still, though the infantry fought hard,
the war was not decided by their bravery. It was the Navy who
delivered the final blow by destroying the Spanish fleet trying to flee
into open water from Santiago harbor. Because of the mismanag
To Roosevelt, the war had been a glorious adventure, proof of his
physical courage and his abilities as a leader. Roosevelt had become
one of the most popular men in America and a permanent figure in
history. (Hill, p. 15) On the final day of the Rough Riders, the
troops all met at Camp Wilkoff and presented their Lieutenant Colonel
with a bronze bronco buster. After the cheering had stopped, Roosevelt
addressed his beloved Rough Riders. ^ I am proud of this regiment
beyond measure. I am proud of it because it is a typical American
regiment. The foundation of the regiment was the cowpuncher^No gift
could have been so appropriate^The men of the West and Southwest ^
horseman, rideman, and the leaders of cattle ^ have been the backbone
of this regiment, which demonstrates that Uncle Sam has another reserve
of fighting men to call upon if necessity arises. Outside of my own
immediate family, I shall never show a strong ties as I do toward you.

I am more than pleased that y! ou feel the same for me. Boys, I am
going to stand here, and I shall esteem it a privilege if each of you
will come up here. I want to shake your hands, I want to say goodbye
to each of you in person.^ (Collin, p. 105-106) With wet eyes, the men
of the 11th United States Horse filed before Roosevelt to say goodbye
to a man who had lead them into battle and into history. Roosevelt^s
Rough Riders were a rare bread of men who had lived, trained, and
fought hard to accomplish a goal many thought would never be possible,
to emerge victorious against difficult and harsh odds to become one of
the renowned regiments ever to be assembled. (Beale, p. 43) Americans
will always remember them as the Western cowboys and the Eastern
polo-players who were lead by a man of immeasurable character and
spirit in a fight that lead them down the path into their place in


1). Beale, Howard K. Theodore Roosevelt and the Rise of America to World
Power. Johns Hopkins Press, Baltimore, Md. 1956 p.14-55

2). Boger, Paul S. The Enduring Vision: A History of the American People. 2nd Edit.
Vol.2. D.C. Heath and Company. Lexington, Mass. 1993. P.714

3). Collin, Richard H. Theodore Roosevelt, Culture, Diplomacy, and Expansion: A
New View of American Imperialism. Louisiana St. Univ. Press, Baton Rouge, La. 1985. P. 3-30

4). Grantham, Dewey W., Editor. Theodore Roosevelt. Prentice-Hall,
Inc. Englewood Cliffs, NJ 1971. P.46-54

5). Gatewood, Willard B. Theodore Roosevelt and the Art of Controversy.
Louisiana St. Univ. Press, Baton Rouge, La. 1970. P. 3-30

6). Hill, Howard C. Roosevelt and the Caribbean. Univ. of Chicago Press, Chicago,
Ill. 1927. P. 1-17

7). Jeffers, H. Paul. Colonel Roosevelt. John Wiley and Sons, Inc. New York, N.Y.
1996. P.134-273

8). Lewis, WM. Draper. The Life of Theodore Roosevelt. United Publishers. 1919.

9). Lorant, Stefan, The Life and Times of Theodore Roosevelt. Doubleday and
Company, Inc., Garden City, N.Y. p. 281-332

10). Morris, Edmund. The Rise of Theodore Roosevelt. Coward, McCann and
Geoghegan, Inc. New York, N.Y. 1979. P. 565-662

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