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Learn more about
Theodore Roosevelt's
military service

    Colonel Theodore Roosevelt

      1st Volunteer Cavalry, U.S. Army and Medal of Honor Recipient

Promoted to Colonel on 31 July 1898 at Santiago de Cuba Big ImageBig Image

Medal of Honor Citation

Lieutenant Colonel Theodore Roosevelt distinguished himself by acts of bravery on 1 July, 1898,
near Santiago de Cuba, Republic of Cuba, while leading a daring charge up San Juan Hill.

Lieutenant Colonel Roosevelt, in total disregard for his personal safety, and accompanied
by only four or five men, led a desperate and gallant charge up San Juan Hill, encouraging
his troops to continue the assault through withering enemy fire over open countryside.

Facing the enemy's heavy fire, he displayed extraordinary bravery throughout the charge,
and was the first to reach the enemy trenches, where he quickly killed one of the enemy with
his pistol, allowing his men to continue the assault. His leadership and valor turned the tide
in the Battle for San Juan Hill.

Lieutenant Colonel Roosevelt's extraordinary heroism and devotion to duty are in keeping with
the highest traditions of military service and reflect great credit upon himself, his unit,
and the United States Army.

Place and date:     San Juan Hill, 1 July 1898.
Citation Date:       16 January 2001.
        Video of the Medal of Honor Ceremony                     Original Muster Roll                     The Round Robin Letter                     Conduct of The War Congressional Testimony

Learn more about
The Rough Riders

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Military Service

Theodore Roosevelt joined the New York National Guard on 1 August 1882. T.R. was commissioned a 2nd Lieutenant, B Company, 8th Regiment.
T.R. was promoted to Captain, and resigned his commission in 1886.
The National Guard Association's most prestigious award is the Theodore Roosevelt Leadership Award for Company Grade Officers

The Rough Riders : A Brief History

On May 6, 1898, Theodore Roosevelt resigned his post as Assistant Secretary of the Navy and volunteered to head a cavalry unit that would fight in Cuba
against Spain in the Spanish-American War of 1898. This cavalry unit eventually came to be known as "Roosevelt's Rough Riders". Volunteers were assembled
from Arizona, New Mexico, Oklahoma, and Indian Territory and included cowboys, gamblers, hunters, prospectors, Buffalo soldiers, college boys, and Native Americans.
The term "Rough Riders" was adapted from Buffalo Bill's famous rodeo show called "Buffalo Bill's Wild West and Congress of Rough Riders of the World".

Theodore Roosevelt was commissioned as a Lt. Colonel in command of the 1st Volunteer Cavalry, a unit part of the 1st Cavalry Bridage that was commanded by
Colonel Leonard Wood. The Rough Riders trained at Fort Sam Houston in San Antonio, Texas. Although the official uniform was a slouch hat with a blue flannel shirt,
brown trousers & leggings, boots, and polka-dot handkerchiefs, Theodore Roosevelt nevertheless had his uniform tailored by Brooks Brothers in Boston.

The Rough Riders (1060 soldiers and 1258 horses & mules) departed San Antonio on May 29, 1898, via the Southern Pacific Railroad and headed toward Tampa, Florida to
await eventual embarkation to Cuba. The unit was bivouacked on the grounds of the Tampa Bay Hotel, currently the site of Plant Hall on the campus of the University
of Tampa. On June 8, 1898, the Rough Riders boarded the ship Yucatan and began to disembark at Daiquiri, Cuba on June 22, 1898.

The Rough Riders fought gallantly throught the Battle of San Juan Heights, losing 5 officers and 95 enlisted men. After the armistice, the Rough Riders returned
to the U.S. and disembarked at Montauk Point, New York, on August 14, 1898. The unit was disbanded on September 15, 1898.

The Battle of San Juan Hill

On July 1, 1898, the Rough Riders were ordered to engage 760 Spanish soldiers defending the San Juan Heights.
The battle that made T.R. famous was actually fought on Kettle Hill, and below is a point-by-point account of the battle.

The numerals on the text description correspond to the numerals on the map below:

I : 13:00 hrs
After taking heavy casualties for almost two hours, the situation facing the troops and Rough Riders is not improving. A gathering of senior officers
meeting behind the Bloody Ford decides that San Juan Heights should be assaulted immediately, to avoid further needless casualties. Messages ordering
the assault are immediately sent down the line of troops and Rough Riders.

II and III : 13:05 hrs
Lt. Col. Theodore Roosevelt and his Rough Riders are in reserve facing the Spanish outlying position on Kettle Hill. He orders the regiment forward, and
troopers from other cavalry regiments deployed in front of them join in the charge. To the left of the charging Rough Riders, the rest of the American
line is also moving forward, heading for San Juan Hill.

IV : 13:15 hrs
Although the main attack on San Juan Hill is pinned down in the open by the withering Spanish fire, the Rough Riders charging Kettle Hill reach the crest.
The outnumbered Spanish defenders retreat back down the other side, heading for the safety of the Heights behind them. With this forward position in
Rough Rider hands, the right flank of the advance is secure.

V : 13:20 hrs
Fire support from Lt. Parker's four Gatling guns, positioned in front of the Bloody Ford, pins down the Spanish defenders around the blockhouse on San Juan Hill.
Further supporting fire comes from the Rough Riders on Kettle Hill.

VI and VII : 13:30 hrs
Lt. Ord of Gen. Hawkin's Brigade leaps up and leads a renewed charge up Kettle Hill. Once across the open ground, the assaulting troops are protected from
Spanish fire by the crest of Kettle Hill itself. As they near the summit the supporting fire ceases. The Americans crest the hill and storm the defences
around the blockhouse. Although many defenders have fled, a few remain to contest their position. Lt. Ord is killed as he jumps over the Spanish trench
in front of the blockhouse. Within minutes the defenders are overwhelmed: many retreat, including the wounded Gen. Linares, who has come to observe the battle.
The blockhouse is now in American hands.

VIII : 13:35 hrs
Theodore Roosevelt on Kettle Hill pleads with his superiors to be allowed to continue the assault against the northern part of San Juan Heights.
Gen. Sumner assents, and Roosevelt leads around 500 assorted Rough Riders and cavalrymen down the hill and up the ridge beyond. Fire support is provided
from the remaining Rough Riders and cavalrymen on Kettle Hill. After a brief resistance, the Rough Riders capture the ridge: all of the Heights are
now held by American troops.

IX : 13:50 hrs
The American troops lining San Juan Heights are now in a precarious position. Subjected to increasing fire from the Spanish defending Santiago, they try
to dig in as best they can. The exchange of fire will continue for the rest of the day, but the Heights are to remain securely in American hands.


We thank Osprey Publishing for their generous permission to reprint this map
taken from pages 74 and 75 of Angus Konstam's
San Juan Hill 1898: America's Emergence as a World Power
Osprey Military Campaign Series #57