Officer & Gent

Rough Riders

Theodore Roosevelt, Cavalry Officer, Rough Rider, Founder of the National Parks and 26th president of the United States of America, is the only president to receive the Medal of Honor.  This amazing individual should be an inspiration for any officer or gentlemen to study and learn from his strengths and weaknesses alike.  I have endeavored to summarize the battle of San Juan Hill, the battle for which the LTC Roosevelt was awarded the MoH as a Calvary officer, which tells greatly the character of the man who would one day lead our nation.

During the year which preceded the Spanish American war, Theodore Roosevelt was the Assistant Secretary of the U.S. Navy.  As war with Cuba loomed, Roosevelt was determined that somehow, he would fight for our nation from the front lines. Roosevelt had several friends who were frequently in and out of Washington, DC, who agreed with his point of view, but none quite so much as an Army surgeon, Dr. Leonard Wood.  Dr. Wood had served honorably and courageously in the campaigns against the Apaches, where he had earned several distinctions including the Medal of Honor. Both men were by nature solders, “born with a keen longing for adventure” and that the possibility of war with Spain would be “as righteous as it would be advantageous to the honor and the interests of the nation.”  After the U.S. warship Maine mysteriously exploded and sank in Havana Harbor, killing 258 U.S. Navy crewmen; war did seemed inevitable.  It was at this time in 1898, when Congress authorized the raising of three cavalry regiments from among the wild riders and riflemen of the Rockies and the Great Plains.  While Theodore Roosevelt was offered command of one of these regiments, he felt that he lacked the experience to rapidly prepare a regiment for war. He sought a compromise with Congress and stated, “I would be quite content to go as Lieutenant-Colonel, if you would make Wood Colonel.

COL Wood and LTC Roosevelt were commissioned and placed in command of the “1st United States Volunteer Cavalry”.  Though this was the official title of their regiment, the public would refer to them as the “Rough Riders”. The mustering-places for the regimented were in New Mexico, Arizona, Oklahoma, and Indian Territory.  COL Wood realized early on the importance of several innovations in warfare and wanted to make sure he and his unit could take advantage of the inventions of smokeless powder and the Krag-Jorgensen carbine, which was already in use with the regular cavalry.  This foresight would serve the rough riders well in the war against Spain, as there were few voluntary regiments, and COL Wood and his men served alongside regulars constantly.

After only a month of train up, the regiment was loaded aboard naval vessels and deployed to Cuba.  Due to the logistics involved with moving the cavalry’s horses, COL Wood was ordered to leave his unit’s horses behind and that only 8 Troops of 70 troopers each were to be taken.  COL Wood took with him MAJ Brodie and LTC Roosevelt to command the two squadrons, being allowed only two squadron commanders. All were willing and eager to fight. Upon landing, each of COL Wood’s men carried with them only 3 days rations and 100 rounds of .30-40 ammunition.  Despite the disorganization of the day, by the late afternoon all of COL Wood’s men, with their ammunition and provisions, landed and were ready for anything that might have turned up. The next morning word came for the soldiers to march. None of the Rough Riders were in very good shape for marching, and moreover they were really horsemen.  Yet they did not halt until LTC Roosevelt had maneuvered them to the extreme front of the formation. The destination was to be Santiago, the first major battle in the war. LTC Roosevelt writes, “On June 30th we received orders to hold ourselves in readiness to march against Santiago, and all the men were greatly overjoyed, for the inaction was trying.”

The heat was intense in the tropics, and the men were unused to operating in these conditions.  From the time of the initial landing there had been a few skirmishes during their advance, and the Rough Riders had sustained light casualties.  Nothing would compare to the fight that was to come, the Battle of San Juan Hill. The orders were simple. Roosevelt was told that the main fighting was to be done by Lawton’s infantry division, which would take El Caney, several miles to his right, while the Rough Riders were simply to create a diversion.  This diversion was determined to come mainly from the artillery. Unfortunately for Roosevelt, the artillery battery was placed right beside his men, and as the artillery opened up, LTC Roosevelt and his men found themselves to be the target of the Spanish defensive fires. Shrapnel rained down on the 1st Volunteer Cavalry, as the Spanish took aim.  Several of LTC Roosevelt’s junior officers were wounded or killed in the barrage; all choosing to forego any type of cover in order to better be seen and lead their men.

Roosevelt sent messenger after messenger to try to find General Sumner or General Wood and get permission to advance. He was just about making up his mind to do so in the absence of orders when LTC Dorst came riding up through the storm of bullets with the welcome command, “to move forward and support the regulars in the assault on the hills in the front.”  The instant he received the orders he sprang on his horse and formed his men in open skirmishing order.

A lot was said about LTC Roosevelt that day. What was said illustrates the value of displaying courage as military officers in hardening and inspiring their soldiers.  Roosevelt told one soldier, “Are you afraid to stand up when I am on horseback?” rallying his troopers to move forward and advance on the enemy.  With the 9th regiment to his front and the 1st to his left, Roosevelt took his men straight up Kettle Hill.  When LTC Roosevelt arrived he spoke to the CPT in command of the regulars which he was ordered to support, “in my judgment we cannot take these hills by firing at them, we must rush them”.

The CPT insisted that his orders were to keep his men lying where they were, and that he could not charge without orders.  “Then I am the ranking officer here and I give the order to charge”.  The CPT hesitated to obey this order when no word had been received by his own COL.  So Roosevelt said, “Then let my men through, sir” and he rode on through the lines followed by the grinning Rough Riders, whose attention had been completely taken off of the Spanish bullets during the dialog between the officers.  The whole line, tired of waiting and eager to close with the enemy, was straining to go forward. The 1st Cavalry came up the hill just behind and partly mixed with the Rough Riders. By this time everyone was greatly excited by the charge, the men cheering and running forward between shots, LTC Roosevelt on horseback riding up and down the line inspiring the advance.

“No sooner were we on the crest than the Spaniards from the line of hills in our front, where they were strongly entrenched, opened a very heavy fire upon us with their rifles.  They also opened upon us with one or two pieces of artillery, using time fuses which burned very accurately, the shells exploding right over our heads.”

On the top of the hill was a huge iron kettle, where they could take cover and have a good view of the charge on the San Juan block-house to the left, where the infantry of Kent, led by Hawkins, were climbing the hill.  Obviously the proper thing to do was to help them, and Roosevelt got the men together and started them volley-firing against the Spaniards in the San Juan block-house and in the trenches around it.  The infantry got nearer and nearer the crest of the hill.  At last he could see the Spaniards running from the rifle-pits as the Americans came on in their final rush.

“Then I stopped my men (from firing their rifles) for fear they should injure their comrades, and called to them to charge the next line of trenches, on the hills in our front, from which we had been undergoing a good deal of punishment.  Thinking that the men would all come, I jumped over the wire fence in front of us and started at the double; but, as a matter of fact, the troopers were so excited, what with shooting and being shot, and shouting and cheering, that they did not hear, or did not heed me; and after running about a hundred yards I found I had only five men along with me. “    

Roosevelt had to return back from his advance, jumped over the wire fence, and head over the crest of the hill.  By this time everybody had his attention, and he leaped over the fence once again, with Major Jenkins beside him this time, and the men of the various regiments which were already on the hill came with a rush, to charge across the wide valley which lay between them and the Spanish entrenchments on San Juan Hill.  They fought fiercely on foot, through the trenches and up the hill, and when they reached the crests found themselves overlooking the city of Santiago.  While Roosevelt was re-forming the troops on the chain of hills, one of General Sumner’s aides, came up with orders to halt where he was, not advancing farther, but to hold the hill at all hazards, which the Rough Riders did with great resolve that 1st day of July, 1898.

It was for the acts this day that LTC Roosevelt was nominated for the Medal of Honor, an honor he never received in his life time.  The Medal of Honor was, however, eventually award to LTC Roosevelt on 16JAN2001, and presented to his great grandson Tweed Roosevelt.  The citation reads:

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.

There is so much that can be learned from the leadership style of Theodore Roosevelt throughout the book.  I found it difficult to summarize some of the materials in the chapters because he had a small story to tell about each soldier on the battlefield.  It seemed as though he truly knew each and every one of his men. You can also tell how much he understands the psychological aspects of what it takes to inspire his men.  He always led from the front. You would not find him cowering behind a rock spouting orders, but rather completely exposed and elevated on horseback, leading from where he could see his men maneuvering on the battlefield, and where they could see him.  At the beginning of the book Roosevelt is analyzing his own short comings and lack of experience with the military. He doesn’t try to bluff his way through, but rather relies on the experience and leadership of other to train himself. It was only through his hard work, dedication, and enthusiasm for the fight that he was able to transform himself into the leader we see charging up San Juan Hill.

Title: Rough Riders
Author: Theodore Roosevelt
ISBN: 9780486450995
Publication date: 2006

Leave a Reply

Close Menu