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The Fight for Santiago. The "Rough Riders" charging up the San Juan Hill, July 1st, and driving the Spanish from their entrenchments. Illustration from McClure's, October 1898

Original title: "Colonel Roosevelt and his Rough Riders at the top of the hill which they captured, Battle of San Juan Hill." US Army victors on Kettle Hill about July 3, 1898 after the battle of "San Juan Hill(s)." Left to right is 3rd US Cavalry, 1st Volunteer Cavalry (Col. Theodore Roosevelt center) and 10th US Cavalry. A second similar picture is often shown cropping out all but the 1st Vol Cav and TR.

Teddy Roosevelt's horse Little Texas led the charge up San Juan Hill during the 1898 Spanish American War

Spanish-American War: 25th Infantry and the Rough Riders at San Juan Hill, 1898

Charge of San Juan Hill during the Spanish American War

Roosevelt joined the U.S. Volunteer Cavalry Regiment which became known as the Rough Riders to fight in the Spanish-American War. He served from May-September, 1898 and quickly rose to colonel. On July 1, he and the Rough Riders had a major victory at San Juan charging up Kettle Hill. He was part of the occupying force of Santiago.

A black and white photo of a painting done in 1898 of Theodore Roosevelt fighting with the Rough Riders in the Spanish American War.

Painting depicts a charge by American troops that led to the capture of the strategically important San Juan Hill during the Spanish-American War, Cuba, July 1, 1898. (Photo by Hulton Archive/Getty Images)

Teddy Roosevelt and the Rough Riders 1898 Spanish American War.The Spanish–American War was a conflict in 1898 between Spain and the United States, effectively the result of American intervention in the Cuban War of Independence.

This is the regimental standard of the 1st U.S. Volunteer Cavalry, better known as the "Rough Riders." The flag was used at San Juan Hill. It is based on the Model 1887 Regular Army cavalry flag, and was hand paimted by Horstman Brothers of Philadelphia.

This is the uniform of a comandante (major) in the Talavera Light battalion. This unit fought at San Juan Hill.

Black soldiers in Spanish American War. Historians say that the Buffalo Soldiers (blacks) charged San Juan Hill before Teddy Roosevelt but in that era it would be politically incorrect to give credits to the black soldiers.

Soldiers pose with Gatling Gun at Cavite. Philippine American War. The Gatling gun saw much action during the Spanish American War. It gained fame in Cuba giving support fire while Theodore Roosevelt and the Rough Riders assaulted San Juan Hill. Several examples were later shipped and used in the war in the Philippines. 

JULY 02: Cuba, 19th century. Humorous illustration on the Spanish-American War concerning Cuba, 1898. Caricature. (Photo by DeAgostini/Getty Images)

The 1st United States Volunteer Cavalry, as is its correct name, was one of three Volunteer Cavalry regiments raised for the Spanish American War and the only one of the three to see action in 1898. The original nickname for the regiment was "Wood's Weary Walkers" after its first commander, Colonel Leonard Wood and in acknowledgment of the fact that despite being a cavalry unit they ended up fighting on foot as infantry.

This image illustrates the typical Spanish soldier on campaign that Americans would face in the fight for Santiago. He is dressed in a Guayabera pattern tunic and trousers of rayadillo.  His jipijapa straw hat is standard for the tropics.  The accoutrements are Model 1886 pattern with some improvements for the Mauser rifle he carries.  This equipment is made of black leather with a brass belt plate embossed with the regimental number "43".

Arsenio Linares y Pombo (1848 – 1914) was a Spanish military man and government official. Born in Valencia, he earned the rank of lieutenant in 1868 and participated in operations against rebellions in Cuba, and in the Carlist Wars on mainland Spain. He occupied posts in the Philippines, Madrid, and Melilla, and later returned to Cuba.

The Spanish–American War was a conflict in 1898 between Spain and the United States, effectively the result of American intervention in the ongoing Cuban War of Independence. American attacks on Spain's Pacific possessions led to involvement in the Philippine Revolution and ultimately to the Philippine-American War.

cables had many key junctions. From the shore near Cienfuegos, cables connected to Havana, the port of Santiago, and then branched off to other Caribbean islands such as Jamaica. The three cables were cut, at sea in several places, disrupting much of the communications between the Spanish and their operations in Cuba. For the mission, the cruiser Marblehead, the gunboat Nashville, and the revenue cutter Windom were dispatched under the command of Captain Bowman H. McCalla.

Webb Cook Hayes was also a Medal of Honor recipient from the Spanish American War

Remember the Maine! Feb. 15, 1898: The USS Maine sinks near Havana, Cuba, helping to spark the Spanish American War. This is part of the metal nameplate from the wreck.