Colonel Theodore Roosevelt, Part Two

By Patrick McSherry* 
Click here to read Theodore Roosevelt's account of the Battle of Kettle and San Juan Hills 

Assistant Secretary of the Navy

In April of 1897 Roosevelt was appointed Assistant Secretary of the Navy as a reward for his staunch and tireless campaigning for the newly elected President, William McKinley. Theodore had been greatly affected the logic of Captain (later Rear Admiral) Alfred Thayer Mahan's "The Influence of Sea Power Upon History" since he had reviewed the book for the Atlantic Monthly in 1890. Now he could begin to put Mahan's beliefs into practice. Mahan had indicated that several key points concerning the Navy were revealed by studying the history of various countries and their Navies. First, that the United States ought to develop a strong Navy capable of extending its power across the ocean where it could defend U.S. interests at a safe distance from the home coastline. Neither Roosevelt or Mahan believed in the Isolationist view that the U.S. coastal defense was the sole use of the Navy. Also, if the Navy was going to be a world force, bases would have to be established at various locations, such as Cuba, Puerto Rico, and Hawaii.

The Secretary of the Navy, John D. Long, a former Governor of Massachusetts and Congressman, was an able administrator. He was not, however, interested in the details of Naval architecture, turret design, coal supplies, drydocks and the like. Long recognized Roosevelt's obvious love for these matters, and relied on Theodore to address them. Long did not share Roosevelt's views on Naval expansion and the need for new capital ships, and, in spite of badgering from Roosevelt, would not fight vigorously for these items.

Long, however, did not like the heat of Washington in the summer and would return to New England .....leaving Roosevelt in Washington. Roosevelt took full advantage of the opportunity. He continued to provide Long an ongoing dialogue by letter of all goings-on. The letters were long and detailed, and tedious as far as the Secretary of the Navy was concerned. Roosevelt suggested that, as summer turned to fall, that the Secretary should not be in any hurry to return, or even answer Theodore's letters. Roosevelt had things well in hand. As the New York Sun stated "the liveliest spot in the Navy Department. The decks are cleared for action. Acting Secretary Roosevelt....has the whole Navy bordering on a war footing. It remains only to sand down the decks and pipe to quarters to action."

During his time in Washington, he began to make acquaintances that would greatly affect the future of the country in the upcoming conflict. He spent time cruising on the new battleship IOWA with the ship's commander, Captain William T. Sampson, who he later served with on the Naval Personnel Board. Sampson was destined to be the future overall commander of the American naval forces off Cuba. One of the places where the Assistant Secretary of the Navy would go to escape the heat of Washington in Summer was the Metropolitan Club. Here he met the president of the Naval Board of Inspection and Survey and the attending surgeon to the president, George Dewey and Leonard Wood respectively. As he got to know these men socially, he began to determine would he could trust and who reflected his views on personal initiative and naval expansion. He would use this information to his advantage when the need arose. Dewey became the hero of the Battle of Manila Bay, and Wood, the Colonel of the "Rough Riders", and Roosevelt's commanding officer. Roosevelt also got to know the commander and executive officer of the USS MAINE, Charles Sigsbee and Richard Wainwright.

Roosevelt knew that war could develop with Spain. He considered Spain's holdings in the Caribbean to be a thorn in the side of the country and its desire to control the hemisphere. There were ongoing conflicts between the Cuban revolutionaries and the Spanish authorities in Cuba, and this lack of stability was not good for the U.S. The lack of stability could bring a stronger Spanish presence to the hemisphere. He wanted to remove foreign control, from the hemisphere, not increase it. Roosevelt also thought that Cuba would be necessary for U.S. to control as it became a world power. Lastly, the Assistant Secretary of the Navy knew that an action against Spain at such a close proximity would give the U.S. military, an untried force, necessary experience. For these reasons, he began making contingency plans for the navy, should war erupt between the United States and Spain. If such a crisis arose, he planned to send naval forces to Cuba and the Philippines, a Spanish possession in the Pacific. He maneuvered to have Commodore George Dewey placed in charge of the Asiatic Squadron, in spite of the fact that other officers had greater seniority. Roosevelt was not concerned about the deaths that may result from any upcoming war. Such sentimentality had no part in his visions of war, however, the romantic and noble notions of war did. He did believe strongly that a strong defense and military would reduce deaths in the long run.

Tensions continued to rise between the United States and Spain, with the United States demanding that the actions against the Cuban people ceased and peace established. Spain responded by recalling General Valeriano Weyler, known as the "Butcher", and replacing him with the more moderate General Ramon y Blanco. McKinley treated this move as very significant, and reported at length on the issue in his annual message to Congress. In the message he rejected United States intervention in Cuba, believing that Spain was acting to create peace. Roosevelt thereafter admitted privately in a letter to a friend that he had "been hoping and working ardently to bring about our intervention in Cuba."

In Cuba, the United States Consul General, Fitzhugh Lee, a former Confederate General in the American Civil War, witnessed a riot by unpaid Spanish officers. The action had nothing to do with United States interests, but Lee misinterpreted the situation. He thought the event was directed against Americans, and requested that a warship be sent to Havana on a friendly visit, however, also indicating United States resolve to protect its interests. The Spanish vessel VIZCAYA would make a similar "friendly" visit to New York. The ill-fated USS MAINE was soon on its way to Cuba, arriving on January 25, 1898 and was greeted without any major protests.

On February 15, 1898, at about 9:30 p.m., the USS MAINE exploded in Havana Harbor. The cause was not known, but over 260 sailors were lost. Immediately rescue boats were launched by various vessels in the Harbor, including the Spanish cruiser ALFONSO XII. From this moment, Theodore Roosevelt believed that trying to prevent the war would be "impossible." Unlike Roosevelt, McKinley, who had seen war firsthand during his service in the American Civil War, did not want to act rashly. On February 25, Secretary Long, weary from the stress of the situation, took the day off. He asked Roosevelt not to "take any such step affecting the policy of the Administration without consulting with the President or intention was to have you look after the routine of the office..." Long stressed that he was "...anxious to have no unnecessary occasion for a sensation in the papers."

Long apparently knew Roosevelt well, but not well enough. When Long was absent Roosevelt sprang into action moving ammunition, coal, ordering the repair of various ships, and readying of them for action, moving to have Congress allow for enlisting unlimited men, and for the purchasing of auxiliary cruisers, etc. Significantly, Roosevelt cabled Dewey to be ready if war were to break out, and gave him his objectives. Long was shocked and angered, however, he did nothing to rescind any of Roosevelt's orders, but he did resolve never to leave the ambitious, young, "bull in a china shop" in charge again.

The War With Spain

Roosevelt Seeks a Frontline Command

Theodore Roosevelt had previously made it know to McKinley and others that if war came, he wanted to leave his post behind a desk in Washington and head for the front. He began putting irons in the fire in this regard. He contacted General Tillinghast and General Greene of the New York National Guard, mentioning that he wanted a frontline position. He also discussed the possibility with Leonard Wood and William Astor Chanler if either of them were planning to raise a regiment.

As time wore on and McKinley continued his efforts to find a peaceful solution, Roosevelt's resolve for war boiled over at a cabinet meeting. He informed the president that only war "was compatible with our national honor, or with the claims of humanity on behalf of the wretched women and children of Cuba." The Congress was for war. The newspapers were calling for war. The people wanted war....but McKinley did not. However, on April 20, McKinley finally gave in, and, with the backing of Congress, informed the Spanish Government that it must free Cuba in three days. The call went out for one hundred twenty-five thousand volunteers. Roosevelt reported that he had the Navy in "good shape". He did. It was ready for war, thanks to the indefatigable efforts of Theodore Roosevelt. Biographer Edmund Morris reported that "never before had it been so strategically deployed and; never was it so ready for instant action."

The "Rough Riders" are Born!

Secretary of War, Russell Alger, offered Roosevelt his own regiment. Roosevelt turned it down, citing his lack of experience and suggested Leonard Wood be placed in charge as Colonel. Roosevelt would serve as Lieutenant Colonel. The unit, officially known as the First United States Volunteer Cavalry. The regiment, nicknamed the "Rough Riders", was made up of an odd but effective assemblage of Western cowboys and Frontiersmen, and Eastern athletes and sons of prominent citizens. Many more people applied and were recommended than ever could be accepted.

Still, Roosevelt continued his duties with the Navy, serving on the Naval War Board, implementing the plans for the war. He was still at his post when Admiral Dewey was able to report his complete destruction of the Spanish Pacific Fleet at Manila Bay. Roosevelt knew he had chosen the right man for the job, and had seen his efforts to ready the navy pay spectacular results.

On May 28, Commodore Schley was able to report to his superiors that he had located the Spanish Fleet at Cuba, and that it was bottled up in Santiago Harbor. Between this and Dewey's victory, the war had the possibility of ending abruptly.....which Roosevelt thought of as bad news. He was in a hurry to get involved at the front before the war ended, after all he told friends that "It will be awful if we miss the fun." He wrote to Colonel Wood, now beginning to train his men in Texas, that the men would have to be on the first expedition to Cuba, trained or untrained. This statements show one of the paradoxes of Roosevelt's character, a deep concern for people, but an almost callous disregard for the possible loss of life in war.

While in Washington, at Wood's request, Roosevelt continued to work to equip the "Rough Riders" with the latest equipment. He outfitted the men in khaki, as opposed to the wool worn by most units. He had the regiment equipped with new Krag-Jorgensen rifles which offered the tremendous advantage of using smokeless powder.

On May 15, 1898, Lieutenant Colonel Roosevelt arrived at his new command near San Antonio, Texas. He quickly took to training the men, while expressing concern over the independent nature that many of the western members of the unit possessed. As Colonel Wood stated, "If we don't get them to Cuba quickly to fight Spaniards there is a great danger that they'll be fighting one another." Roosevelt still had a lot to learn though. His desire to have the men like him, in Wood's opinion, was taken to a dangerous level. One hot afternoon he stopped his command at a local resort, and allowed the men to drink, at his expense. He was severely chastised by Colonel Wood. Roosevelt quickly realized his error, and the need for Wood's reproach. He apologized to Wood, calling himself "the damndest ass within ten miles of this camp". Still drilling went ahead, and the men, both the Eastern college athletes as well as the Western cowhands, learned quickly.

On May 29, 1898, the Rough Riders headed for Tampa Bay, Florida, where the government had already gathered a large number of troops in preparations for its actions against Cuba. When they arrived, at the end of the infamous one-track railway, no one was present to direct them into camp. This was an indication of things to come in the camp of thirty-thousand men. Roosevelt and Wood would have to rely on their own initiative to get their troops into action.

Off to Cuba!

When the order came to board the vessels to head for Cuba, confusion reigned. The Rough Riders were told be at a certain track to meet their train to the docks. They made it in time, but the train did not. They were ordered to another track, but still no train or organized plans. Roosevelt and Wood knew that the orders were that if the men were not at dockside by the morning, they would be left behind. Roosevelt commandeered an empty coal train to carry his men the nine miles to the dock.

Though he had gotten his men to the dock by the appointed time, Roosevelt's problems did not end. Again, Roosevelt's decisiveness won out. He fought his way through the ten thousand bewildered men on the dock, and found a quartermaster who pointed to the YUCATAN out in the channel as the transport for his men. Unfortunately, the vessel was also assigned to the Second Regular Infantry and the Seventy-first New York Volunteer Infantry. Knowing that the vessel could not take them all. Roosevelt ran his men to the point where the YUCATAN docked, and took possession of her before the other units knew what had happened. After a face-off with an officer of the Seventy-first New York, Roosevelt won out, and his men were aboard by night, and "packed like sardines." The situation was unpleasant and made worse by the stifling heat, and lack of supplies. Worst of all was that a false alarm about the presence of Spanish naval vessels held the ships in port under these terrible conditions until June 13. Roosevelt fumed over the inefficiencies and ridiculousness of the army bureaucracy. He found the entire situation in and around Tampa Bay to be beyond belief. Finally, the U.S. forces set a course for Cuba.

At 3:30 in the morning on June 22, the bugles sounded aboard the YUCATAN. However, it was hours before the landing was begun. The landing itself could have been a debacle had the Spanish offered resistance, but they did not. An angry Theodore Roosevelt wrote that "we did the landing as we had done everything else - that is, in a scramble." There were not enough boats, men were dropped off too far off shore and drowned under the weight of their equipment. The horses were also landed in a haphazrd manner. Newsreel photographer Alfred Smith, who Roosevelt, with his flair for publicity, had allow to join him, stated that the horse handling had Roosevelt "snorting like a bull", yelling obscenities, and howling "Stop that goddamned animal torture". One of Roosevelt's two horses were lost. Roosevlt later recorded that it was lucky that they were at war with "a broken down power, for we should surely have a deuced hard time with any other."

Las Guasimas

By the next afternoon, Roosevelt found himself advancing with his men against the Spanish troops at Las Guasimas. The Rough Riders, and Colonel Wood and Lieutenant Colonel Roosevelt were basically ambushed as they rested on a forced march to join General Young's two pronged attack. The Rough Riders fired back, but were initially unable to locate the source of the deadly fire because of the Spanish infantry's use of smokeless powder. Getting their range, the Americans caused the Spanish to flee, and the Rough Riders advanced. Lieutenant Colonel Roosevelt narrowly missed being shot in the head, as a Mauser bullet penetrated a tree which he was hiding behind. Luckily, the Lieutenant Colonel was peeking out from behind the tree, with his head exposed, but out of the line of fire of this particular bullet. Still, the bullet shots splinters and dust into his face and eyes. At the battle, Roosevelt showed the "coolness, the calm judgement, the towering heroism, which made him, perhaps, the most admired and best loved of all Americans in Cuba." Roosevelt had proved himself as capable under fire as he had been behind a desk in Washington, and in the saddle on the training grounds in Texas. In the hour and half fight, the Rough Riders lost eight men dead, including Captain Allyn Capron, Jr., a fifth generation military man from Brooklyn, lately of Oklahoma, and called by Roosevelt "the best soldier in the regiment", and Sergeant Hamilton Fish, the son of a prominant New York family. The unit also suffered thirty-four wounded.

The actions against the Spaniards had been difficult. Even the venerable old Civil War commander General Joe Wheeler had been laid low by the excitement, efforts and fever. This caused a change in the command structure, and the promotion of Colonel Wood to Brigade Commander. That left Roosevelt as the new commander of the Rough Riders with the rank of Colonel.

Kettle Hill and San Juan Hill - The "Crowded Hour"

June 30, 1898 proved to be one of the most significant dates in the life Theodore Roosevelt. As he advanced toward the San Juan River, a Spanish shell burst overhead, with shrapnel hitting Roosevelt in the wrist, raising a hefty lump. The blast wounded several other Rough Riders and regulars. Roosevelt and the Rough Riders formed the head of the their brigade and were ordered by Wood to follow the First Brigade and ford the San Juan River. The temperature rose to over one hundred degrees Fahrenheit. In the stifling heat, the Rough Riders waited as the advance stalled, the troopers finding whatever cover they could from the enemy fire.

Orders came for the Rough Riders to advance up Kettle Hill to support the Regulars, who were attacking San Juan Hill from a different direction. Roosevelt, still riding Texas, his horse, exhorted his men to ride forward, pushing his way through. The Rough Riders found themselves pushing the troops in front of them, and Roosevelt found himself leading the entire advance. Observers commented that the advance had no chance, the men too sparse and the Spaniards too well entrenched.

Roosevelt continued to ride Texas until about forty yards from the summit of the hill where there was a wire fence. Both he and Texas had been grazed by enemy bullets. Roosevelt dismounted and released Texas, and climbed through the fence. He was outpaced by his orderly, Henry Bradshar, and closely followed by some of the Rough Riders. Quickly they reached the summit, with men of the Rough Riders and the Ninth Infantry all claiming to be the first. Once they gained the summit, the Americans were hit by both heavy rifle and cannon fire, forcing them to find cover in the Spanish trenches and behind the sugar kettle from whence the hill received its name. Roosevelt*s men kept up a steady fire on the Spanish line which they had penetrated. This combined with the advance of troops on their front caused the Spanish line to crumble.

Theodore Roosevelt ordered a charge and took off after the Spaniards on adjacent San Juan Hill. Unbeknownst to him, only five men followed him, and three of them fell wounded within a hundred yards. The remaining two held the ground while an angry Roosevelt returned to the main line through the continuing fire and confronted his men for not following. In the intense activity of the moment, the troops had not heard the order nor seen their leader charging the enemy almost single-handedly. Now the charge became general. The Spanish trenches were cleared and the Americans began a tenuous hold on San Juan and Kettle Hills. Rough Riders had lost 89 of its 490 men killed or wounded. This would always be Roosevelt's most "crowded hour". Most experts agree that Roosevelt*s personal valor and leadership was the single strongest element leading to the success of the attacks on the heights.

The Rough Riders dug in on San Juan Hill, foraging for food and waited for a counterattack from the Spanish. The Spanish kept up a steady fire, but no major counterattack came. Roosevelt and his men held their position in the uneasy seige of Santiago until July 10, when they were ordered to guard the El Caney Road. The Spaniards surrendered on July 17.

The Aftermath

Now Roosevelt had a new problem. He had to maintain discipline amongst men not used to the boredom that came with peace. At the same time, sickness in the regiment began to rise. Seldom was more than half of the command fit for active duty. Malaria and some Yellow Fever had hit the U. S. forces. Fear of importing these diseases was one reason for the delay in shipping the troops home. The need to remove the troops from Cuba was obvious to the officers in the field, but many were unwilling to risk their military careers by stating so officially. A meeting of brigade and division commanders was held which Roosevelt attended, as he was now brigade commander. The medical situation was discussed, and when it beame apparent that none of the officers wanted to address the disease issue officially, Roosevelt, a volunteer and not a careerman, offered to write the report.

The Report, in which Roosevelt was quite frank about the need for the troops to leave Cuba was not accepted by overall commander General Shafter, who, instead, passed the report to the Associated Press instead. President McKinley and the Secretary of War first learned of the problem by reading of Roosevelt's report in the newspaper. The War Department had already planned to remove the troops, but to the public it appeared that Roosevelt's report had an affect. The impact on Roosevelt was not good as official anger mounted aganst him. Secretary of War Alger was so annoyed that when many officers recommended Roosevelt be given the Congressional Medal of Honor, the Secretary refused to endorse it. Without his support, the effort failed, a great disappointment to the future President.

Homeward Bound

On August 7, 1898, the Rough Riders and Roosevelt boarded the transport MIAMI and headed north to Montauk., New York. After arriving, someone in the crowds yelled to ask Roosevelt how he felt. Roosevelt responded that "I've had a bully time and a bully fight. I feel as big and as strong as a Bull Moose!" By this time, Roosevelt was one of the most famous men in America. A legend was born.

Roosevelt's Rough Riders honored him by presenting him a famous bronze sculpture by Frederick Remington, "The Bronco". On September 15, 1898, the unit's flag was furled, and the Rough Riders were mustered out.

Already efforts were afoot for Roosevelt's next adventure, this time into politics. His popularlity was reflected in his being elected as the new Governor of New York in the fall of 1898. 


(As a service to our readers, clicking on title in red will take you to that book on

*(Jeffers, H. Paul, Colonel Roosevelt: Theodore Roosevelt Goes to War, 1897-1898. (New York: John Wiley & Sons, Inc., 1996). ISBN: 0-471-12678-0) (As a service to the reader, clicking on the red link will take you to this book on

To Be Continued...

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