On April 6, 1897 Roosevelt received word that he had been appointed Assistant Secretary of the Navy. Roosevelt was well fitted for the position, as he had become somewhat of an expert in naval warfare during the research for his book Naval War of 1812. In the book Roosevelt preached how the United States, since the War of 1812, had let its navy decline. He maintained that the United States still needed to strengthen its navy both to protect American interests and to keep the Europeans from breaching the Western Hemisphere. Roosevelt was a strong nationalist and an expansionist, and without a strong navy his aspirations for the nation could not come to fruition.

Roosevelt along with Secretary of the Navy John Long began building the navy. To the extent public opinion and Congress would allow, they added cruisers and battleships. Roosevelt wrote in his autobiography,

"I abhor unjust war. I abhor injustice and bullying by the strong at the expense of the weak, whether among nations or individuals. I abhor violence and bloodshed. I believe that war should never be resorted to when, or so long as, it is honorably possible to avoid it. I respect all men and women who from high motives and with sanity and self-respect do all they can to avert war. I advocate preparation for war in order to avert war; and I should never advocate war unless it were the only alternative to dishonor. I describe the folly of which so many of our people were formerly guilty, in order that we may in our own day be on our guard against similar folly."

Yet despite this Roosevelt was beating the war drum as loud as anyone in the country. Roosevelt was preaching intervention in Hawaii to keep the Japanese from taking it. He was making a strong argument for building a canal through Central America to make it easier for our fleet to move between the two great oceans. And loudest of all he was looking for a fight with Spain to flex our strength against one of the weakest of the European colonial powers. Roosevelt summed up his reasons for wanting war with Spain in his autobiography,

"Our own direct interests were great, because of the Cuban tobacco and sugar, and especially because of Cuba's relation to the projected Isthmian Canal. But even greater were our interests from the standpoint of humanity. Cuba was at our very doors. It was a dreadful thing for us to sit supinely and watch her death agony. It was our duty, even more from the standpoint of National honor than from the standpoint of National interest, to stop the devastation and destruction. "

A rebel faction in Cuba was fighting desperately to overthrow the Spaniards. In an effort to destroy the rebellion the Spaniards began a policy known as reconcentrado. According to this policy all of the people were relocated from their land into camps. Any one not in a camp was then considered to be a rebel and was thus executed. Problems in the camps quickly developed as the water went bad, food supplies fell short, and sanitary conditions became atrocious. Hundreds died of disease in the camps.

During the summer of 1897 Secretary Long, due to health problems, took long vacations away from Washington leaving Roosevelt in charge. Roosevelt for his part thrived on the power, and was often brought into consultation with McKinley. In this way he earned the trust of the President and Secretary Long.

The war hawks were screaming in this country for intervention, however, McKinley, a very good politician, was sitting back waiting to find out how public opinion would go. Rioting in Cuba prompted the American consul to request the U.S. send a warship for their protection. McKinley, after resisting the request for a short period of time, finally got permission from the Spaniards to send the battleship Maine to Havana's harbor. The ship arrived the first week in February 1898 and tensions remained high. On the evening of February 15 a horrific explosion pierced the night sky as the ship's hull was blown to shreds. When the smoke cleared all but the mast of the ship and a small portion of its superstructure lay on the bottom along with approximately 250 Americans. The blast brought both fence riders and peace lovers alike to the side of the war hawks in America, and the cries could be heard around the country "Remember the Maine! To Hell with Spain!" Quickly the American's prepared for war.

The Navy Department worked franticly after the explosion o the Maine to prepare for war. Secretary Long was still suffering from health problems and on the weekend of February 25 left the office for a much-needed rest. Roosevelt for his part flew into action. He poured over the maps, repositioned ships, and stockpiled fuel and ammunition in strategic locations. Most importantly Roosevelt sent the following confidential note to Commodore George Dewey.

"Secret and confidential. Order the squadron except Monocacy to Hongkong. Keep full of coal. In the event of declaration of war Spain, your duty will be to see that the Spanish squadron does not leave the Asiatic coast, and then offensive operations in Philippine Islands. Keep Olympia until further orders.

Long was somewhat surprised by Roosevelt's rash actions in his absence, but for the most part let most of his orders stand. The U.S. with Roosevelt's help was closer to war with Spain than ever. When investigations in the explosion of the Maine showed overwhelming evidence that the ship had not exploded from an internal explosion, but had been blown up from the outside, McKinley was forced by the wave of public opinion to declare war with Spain. McKinley sent the request for military intervention to the Congress on April 11, 1898 and after about a week of debate in Congress the country and Roosevelt would have their war.

Since his father had told him to "make his body" as a child, Roosevelt had pushed himself to the limits to prove himself. When war finally came there could be no denying TR from his chance to prove himself in battle. In his letters Roosevelt expressed these opinions in the following comments. "It does not seem to me that it would be honorable for a man who has consistently advocated a warlike policy not to be willing himself to bear the brunt of carrying out that policy_" "I have a horror of people who bark but don't bite." Although many of his friends advised against him going to war, Roosevelt would not be denied that opportunity as his father had been at the request of his mother during the Civil War.

When McKinley and Long were convinced of Roosevelt's determination to fight, they agreed to help him. The war cry was so strong, that in his home state of New York he had little chance of getting a commission. In stead he opted for raising a special unit of cavalry from the west which had just been authorized by Congress. Roosevelt approached Secretary of War Russell Alger and reminded him that he himself had once been a cowboy and a hunter in the west and thus was fully qualified to be a part of this special commision. Alger agreed that TR was qualified and offered him the command of one of the regiments. Roosevelt knew of his own lack of military experience and knowledge as to how to outfit such a regiment, and thus declined the command, and instead opted for a lieutenant-colonelcy under Leonard Wood. Roosevelt knew that there were many regiments forming and that through his on the job training as to what a cavalry colonel was supposed to do might cost him a chance to fight at all.

Wood was a career soldier and with his expertise and Roosevelt's influence could quickly have the First Volunteer Cavalry ready for action. The First Volunteer Cavalry quickly attracted the attention of the national press. This group of cowboys and hunters conjured up all kinds of patriotism among the American people as the group combined many of America's highest ideals; the spirit of dropping everything to go off and fight for your country, and the free spirit of the cowboy. As for its military purposes as a cavalry unit, no better riders existed then the western cowboy, and their ability with a rifle was unsurpassed. There couldn't be a better story to attract the American's interest and excitement. This regiment was quickly christened the "Rough Riders."

The group was comprised of men from Arizona, New Mexico, Oklahoma, and the Indian Territory. The regiment was originally to contain only 780 men, but when more federal funding became available the ceiling was raised to 1,000 men. The regiment was not difficult to fill as the number of applicants exceeded 23,000. To join the cowboys and hunters would be a score of Indians, a few topnotch Ivy League athletes, and some other fox hunters and friends of Roosevelt from the East. The regiment would gain its invaluable training just outside of San Antonio Texas. Although these men, were the best riders in the country, they knew nothing of military drill. The men learned their drill quickly, but as time passed Roosevelt feared that his regiment would never see service.

Following Roosevelt's orders, at the outset of war Dewey took his fleet to the Philippines and caught the Spanish fleet unprepared and soundly defeated them. With the Spanish fleet destroyed, Dewey took Manila Bay and became an instant war hero. With this quick an easy victory, Roosevelt feared that the Spanish would give up Cuba with out a fight. Roosevelt wrote to his now very influential friend in the Senate, Henry Cabot Lodge requesting that the Rough Riders be sent as one of the first units into action. If there wasn't going to be action in Cuba or Puerto Rico, then send them to the Philippines.

Roosevelt was very impressed with the speed and determination the Rough Riders worked at learning the drills necessary to get them into action. One day at the end of a drill Roosevelt announced to the men to dismount and go to their favorite establishment, where he would buy the drinks. He was treated by great hurrahs for the lieutenant colonel. Roosevelt, as always, wanted to be liked and treated as one of the boys of the west. When Colonel Wood heard about the incident he called Roosevelt into his tent for a light reprimand. Wood explained that an officer drinking with the men was not conducive to good discipline. Roosevelt left the tent accepting the reprimand and with in a few minutes returned to Wood's tent. He entered the tent saluted the colonel and said, "Sir, I consider myself the damnedest ass within ten miles of this camp! Good night, sir!"

Roosevelt's pleas to Lodge paid off as the Rough Riders were given their orders to move. The people of San Antonio had mixed feelings about the departure of the Rough Riders. Although the boys had caused some problems in the town on more than one occasion, they had also brought a lot of attention to the town through the coverage of the national press. In an attempt to say goodbye, the town threw a party for the boys of the First Volunteer Cavalry. During the evening festivities a band was set to play some stirring numbers. The bandleader, Professor Carl Beck, in an attempt to bolster the percussion section for one of the numbers had a cannon fired during an exceptionally rousing part of the music. Someone failed to tell the Rough Riders about the cannon fire, and the boys assumed they were under attack. When the lights went out the chaos was elevated even more with many of the Rough Riders firing into the dark, believing they were under attack my Spanish sympathizing Mexicans. After a few minutes peace was restored and the celebration drew to a close, with many of the spectators being thankful to have escaped with their lives.

The journey to Cuba would commence by way of a four-day train ride with men and horses to Tampa, Florida. Tampa would prove to be a total debacle with thirty thousand men gathered in one place and a total lack or organization. Roosevelt wrote of the situation, "No words could describe to you the confusion and lack of system and the general mismanagement of affairs here." There was a lack of food, and duplicated orders as to who would leave on which vessel. The Rough Riders would fall victim to the latter case. Roosevelt learned that the ship, which was to transport his regiment, had also been assigned to two other regiments. Unfortunately, the ship in question was only large enough to hold one regiment. Roosevelt later recounted how he won his 'first victory of the war'. He left a strong guard watching the baggage and marched the rest of the men at double-quick to arrive at the ship just as it was ready to be embarked. When the other two regiments arrived, they were too late to get on board. For the Rough Riders this first 'victory' was a mixed blessing. Intelligence had come in reporting that the Spaniards had war ships off of the coast and, even though this story was far fetched, the navy didn't want to risk having its first transports sunk with hundreds of men on board. For this reason the departure was delayed for more than a week. With all of the men on board, and thousands of others packed into Tampa, the raw sewage flowing into the harbor created an enormous stench. The second problem which occurred with the shipment of the Rough Riders was that fact that the ship was so large that there wasn't enough room for all of the horses, so only the officers' mounts were boarded. Thus the regiment recruited mainly for their riding skills would go into battle on foot.

When finally the armada was under steam it would contain 48 ships traveling in three columns. During the trip Roosevelt would comment on the immensity of the role he believed that he and his men were carrying out. "It is a great historical expedition, and I thrill to feel that I am part of it. If we fail, of course we share the fate of all who do fail, but if we are allowed to succeed (for certainly we shall succeed, if allowed) we have scored the first great triumph in what will be a world movement."

The landing at Daiquiri proved to be almost as big a debacle as the departure from Tampa. Almost no one on board the ships had any experience of disembarking into the surf with packs and animals. The horses and mules were driven off into the surf in hopes that they would swim to shore. Many of them would swim from boat to boat, or nearly reach shore, and again turn back to sea. As a result many of the horses and mules drowned. Roosevelt himself lost one of his two mounts. The men struggled as well carrying packs and trying to avoid each other and the frantic animals. Fortunately, only two men drowned in the process and even more fortunately the Spaniards after a brief bombing from the warships left the beach undefended.

The first night was spent under a clear sky on the beach. The next day lean-tos were constructed of palm branches to ward off the rays of the scorching sun. The primary target for the assault was Santiago de Cuba, which was about a fifteen mile march north of the landing site. Once again confusion reigned but Roosevelt and Wood, under the command of the old Confederate hero Joseph Wheeler, managed to march hard and fast to get to the front of the column. For the cowboys used to riding, the march was a difficult one at best and many of them shed their packs, blankets and canned meat, carrying only their weapons and ammunition.

The hard march paid off for the Rough Riders the next day as, being at the head of the column, they were involved in about a 2 « hour struggle against a very outnumbered Spanish force at Las Guasimas. Out of the 500 men engaged from the Rough Riders a dozen fell mortally wounded, and about sixty severely or slightly wounded. The fight, however, energized the men and drove them on with a new vigor. Once again the men would face logistics problems, with little or no food, and a lack of shelter. At one point Roosevelt requisitioned from a commissary sergeant eleven hundred pounds of beans which were earmarked for officers. When the staff sergeant informed Roosevelt that the beans were for officers only, TR informed him that the beans were for his officers. The staff sergeant again bulked saying that there was no way that Roosevelt's officers could eat eleven hundred pounds of beans. The sergeant finally gave in to TR and informed him that they would probably come out of his pay. Roosevelt wound up paying for the beans, but his men got to eat.

On June 30, after many days of sitting idle, the orders were finally given to move out. The men traveled in extremely high temperatures, with little or no breeze through the thick jungles. This extreme exertion brought many of the men to the verge of heat exhaustion. The next day, when the battle finally began, Wood and Roosevelt found themselves in a direct line between the two opposing armies artillery assaults. During the artillery barrage Roosevelt received a slight wound to the arm. Despite heavy shelling, Roosevelt mounted his horse and led his men to a more sheltered spot. When the orders were given to move, the Rough Riders reached a ford over San Juan River about the same time as another unit. The Spaniards using German Mausers rifles, leveled a heavy fire on the American forces from their entrenched positions high upon San Juan and Kettle Hills. To make matters worse the second American unit was dragging a tethered observation balloon giving the Spanish artillery a perfect target which in turn increased the fire on TR's men. Roosevelt finally received orders to advance, and once again on horseback encouraged his men forward through other regiments in an effort to reach the front. When his men reached the base of Kettle Hill a group of regulars were the only ones ahead of them. Roosevelt was dismayed that these men were lying down and would not charge the hill. Roosevelt, not being able to find the colonel of the Regulars gave the order to advance on the hill. The captain of the Regulars would not take his orders from a lieutenant colonel of the volunteers and thus remained in place. Roosevelt furious at this then shouted, "If you don't wish to go forward, let my men pass." The Rough Riders then charged up the hill, with the regulars, out of embarrassment, quickly on their heals. Roosevelt was finally forced to dismount when he came to a wire fence on his approach up the hill. He continued leading the charge on foot, being one of the first to reach the top. The Spaniards fled from Kettle Hill and the Rough Riders began to celebrate their victory. The celebration was short lived, however, as artillery fire came fast an furious on their position from the nearby Spanish guns on San Juan Hill. Casualties on the Kettle Hill were mounting quickly with no real cover, so Roosevelt, seeing other American forces charging San Juan Hill, gave the order to attack and charged out over the open ground to assault the opposing hill. He had charged about 100 yards when he realized that his men hadn't heard the order to attack and that he was virtually on his own. He ran back to the position at the top of the hill and this time the men charged with him up toward the Spaniards positions on San Juan Hill. The Spaniards, being outnumbered fifteen to one, took off for nearby Santiago leaving their cooked dinners behind for the Americans to enjoy. The casualties for the day had been high for the Americans, losing more than two hundred killed on San Juan and Kettle Hills with nearly 1,000 men wounded. Roosevelt became an instant war hero and was promoted to Colonel. The Rough Riders part in the fighting was over. The Spanish fleet in an attempt to keep from being destroyed tried to make a run for it and all five ships were destroyed. With the ships being gone Santiago did not seem as important and thus General Shafter, the commanding general of the American forces in Cuba, laid siege to Santiago, which after two weeks was surrendered. By August 12th Washington had a preliminary peace accord from the Spanish. The only battle remaining for the Rough Riders was the battle of yellow fever, which took a heavy toll on the men. The men were taken from Cuba to Montauk, Long Island to spend a brief time in quarentine.

Roosevelt's popularity was at an all time high and with his status of war hero he was catapulted into the Republican nomination for governor of New York. Roosevelt's campaign for governor sounded more like a run for the presidency as he pounded home the need for a stronger navy and for the United States to step up to its responsibility as a new world leader. The race was a bitter one and a very close one with the emphasis of both parties to attack the machines behind the opposite candidate. Roosevelt swung the tide when he declared that a vote for him was a vote for a war hero and a vote against Croker of Tammany Hall. Roosevelt squeaked by with an eighteen thousand vote majority in the 1.3 million cast.