While the United States tried to preserve strict neutrality in the struggle between Spain and Cuba, Americans were getting sick of watching the Cubans being slaughtered. After damage had been done to United States-Spanish relations, the United States battleship Maine, anchored off Havana, exploded, killing 260 crewmembers. "Remember the Maine!" became the battle cry throughout the United States. Congress declared war on April 25, 1898.
Rough Riders
The most famous of all the units fighting in Cuba, the "Rough Riders" was the name given to the First U.S. Volunteer Cavalry under the leadership of Theodore Roosevelt. Roosevelt resigned his position as Assistant Secretary of the Navy in May 1898 to join the volunteer cavalry. The original plan for this unit called for filling it with men from the Indian Territory, New Mexico, Arizona, and Oklahoma. However, once Roosevelt joined the group, it quickly became the place for a mix of troops ranging from Ivy League athletes to glee-club singers to Texas Rangers and Indians.
Roosevelt and the commander of the unit Colonel Leonard Wood trained and supplied the men so well at their camp in San Antonio, Texas, that the Rough Riders were allowed into the action, unlike many other volunteer companies. They went to Tampa at the end of May and sailed for Santiago de Cuba on June 13. There they joined the Fifth Corps, another highly trained, well supplied, and enthusiastic group consisting of excellent soldiers from the regular army and volunteers.
The Rough Riders saw battle at Las Guásimas when General Samuel B. M. Young was ordered to attack at this village, three miles north of Siboney on the way to Santiago. Although it was not important to the outcome of the war, news of the action quickly made the papers. They also made headlines for their role in the Battle of San Juan Hill, which became the stuff of legend thanks to Roosevelt's writing ability and reenactments filmed long after.
Source: Hispanic Division Library of Congress
The Medal of Honor Issue
The Medal of Honor was awarded to twenty-eight men in the battle for Santiago, but Roosevelt failed to secure it. The people loved him, but Washington did not. Although several people in high positions campaigned for him to get the medal, it was not to happen in his life time.
Colonel Roosevelt…led a very desperate and extremely gallant charge on San Juan Hill, thereby setting a splendid example to the troops encouraging them to pass over the open country intervening between their position and the trenches of the enemy. In leading this charge, he started off first, as he was supposed to, with quite a following of men, but soon discovered that he was alone. He then returned and gathered up a few men and led them to the charge…an extremely gallant one, and the example set a most inspiring one to the troops in that part of the line [and] had a very encouraging effect and had great weight in bringing up the troops behind him.
— A recommendation to Secretary of War Alger that Roosevelt be presented the Medal of Honor.
Over one hundred years later, he would finally be recognized for his bravery leading charges at Kettle Hill and San Juan Heights during the Battle of San Juan Heights in Cuba. On January 16, 2001, Theodore Roosevelt became the first President to receive the Medal of Honor, the highest award for Military Service given in the United States. Accepting the award from the President on behalf of the Roosevelt family is great grandson Tweed Roosevelt.

President Clinton presenting Medal of Honor to Roosevelt's
great grandson Tweed Roosevelt, January 16, 2001.