Home  »  Theodore Roosevelt: An Autobiography  »  VII. The War of America the Unready. Appendix B: The San Juan Fight

Theodore Roosevelt (1858–1919). An Autobiography. 1913.

VII. The War of America the Unready. Appendix B: The San Juan Fight

The San Juan fight took its name from the San Juan Hill or hills—I do not know whether the name properly belonged to a line of hills or to only one hill.

To compare small things with large things, this was precisely as the Battle of Gettysburg took its name from the village of Gettysburg, where only a small part of the fighting was done; and the battle of Waterloo from the village of Waterloo, where none of the fighting was done. When it became the political interest of certain people to endeavor to minimize my part in the Santiago fighting (which was merely like that of various other squadron, battalion and regimental commanders) some of my opponents laid great stress on the alleged fact that the cavalry did not charge up San Juan Hill. We certainly charged some hills; but I did not ask their names before charging them. To say that the Rough Riders and the cavalry division, and among other people myself, were not in the San Juan fight is precisely like saying that the men who made Pickett’s Charge, or the men who fought at Little Round Top and Culps Hill, were not at Gettysburg; or that Picton and the Scotch Greys and the French and English guards were not at Waterloo. The present Vice-President of the United States in the campaign last year was reported in the press as repeatedly saying that I was not in the San Juan fight. The documents following herewith have been printed for many years, and were accessible to him had he cared to know or to tell the truth.

These documents speak for themselves. The first is the official report issued by the War Department. From this it will be seen that there were in the Santiago fighting thirty infantry and cavalry regiments represented. Six of these were volunteer, of which one was the Rough Riders. The other twenty-four were regular regiments. The percentage of loss of our regiment was about seven times as great as that of the other five volunteer regiments. Of the twenty-four regular regiments, twenty-two suffered a smaller percentage of loss than we suffered. Two, the Sixth United States Infantry and the Thirteenth United States Infantry, suffered a slightly greater percentage of loss—twenty-six per cent and twenty-three per cent as against twenty-two per cent.


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To be Colonel by Brevet

Lieutenant-Colonel Theodore Roosevelt, First Volunteer Cavalry, for gallantry in battle, Las Guasima, Cuba, June 24, 1898.

To be Brigadier-General by Brevet

Lieutenant-Colonel Theodore Roosevelt, First Volunteer Cavalry, for gallantry in battle, Santiago de Cuba, July 1, 1898. (Nominated for brevet colonel, to rank from June 24, 1898.)

July 17, 1898.

Washington, D. C.
(Through military channels)
SIR: I have the honor to invite attention to the following list of officers and enlisted men who specially distinguished themselves in the action at Las Guasimas, Cuba, June 24, 1898.

These officers and men have been recommended for favorable consideration by their immediate commanding officers in their respective reports, and I would respectfully urge that favorable action be taken.


In First United States Volunteer Cavalry—Colonel Leonard Wood, Lieutenant-Colonel Roosevelt.
Major-General United States Volunteers, Commanding.

June 29, 1898.

SIR: By direction of the major-general commanding the Cavalry Division, I have the honor to submit the following report of the engagement of a part of this brigade with the enemy at Guasimas, Cuba, on June 24th, accompanied by detailed reports from the regimental and other commanders engaged, and a list of the killed and wounded:


I cannot speak too highly of the efficient manner in which Colonel Wood handled his regiment, and of his magnificent behavior on the field. The conduct of Lieutenant-Colonel Roosevelt, as reported to me by my two aides, deserves my highest commendation. Both Colonel Wood and Lieutenant-Colonel Roosevelt disdained to take advantage of shelter or cover from the enemy’s fire while any of their men remained exposed to it—an error of judgment, but happily on the heroic side.
Very respectfully,
Brigadier General United States Volunteers, Commanding.


December 30, 1898.

Washington, D. C.
SIR: I have the honor to recommend Hon. Theodore Roosevelt, late Colonel First United States Volunteer Cavalry, for a medal of honor, as a reward for conspicuous gallantry at the battle of San Juan, Cuba, on July 1, 1898.

Colonel Roosevelt by his example and fearlessness inspired his men, and both at Kettle Hill and the ridge known as San Juan he led his command in person. I was an eye-witness of Colonel Roosevelt’s action.

As Colonel Roosevelt has left the service, a Brevet Commission is of no particular value in his case.

Very respectfully,
Major-General United States Volunteers.

December 17, 1898.

MY DEAR COLONEL: I saw you lead the line up the first hill—you were certainly the first officer to reach the top—and through your efforts, and your personally jumping to the front, a line more or less thin, but strong enough to take it, was led by you to the San Juan or first hill. In this your life was placed in extreme jeopardy, as you may recall, and as it proved by the number of dead left in that vicinity. Captain Stevens, then of the Ninth Cavalry, now of the Second Cavalry, was with you, and I am sure he recalls your gallant conduct. After the line started on the advance from the first hill, I did not see you until our line was halted, under a most galling fire, at the extreme front, where you afterwards entrenched. I spoke to you there and gave instructions from General Sumner that the position was to be held and that there would be no further advance till further orders. You were the senior officer there, took charge of the line, scolded me for having my horse so high upon the ridge; at the same time you were exposing yourself most conspicuously, while adjusting the line, for the example was necessary, as was proved when several colored soldiers—about eight or ten, Twenty-fourth Infantry, I think—started at a run to the rear to assist a wounded colored soldier, and you drew your revolver and put a short and effective stop to such apparent stampede—it quieted them. That position was hot, and now I marvel at your escaping there.…
Very sincerely yours,

December 17, 1898.

I hereby certify that on July 1, 1898, Colonel (then Lieutenant-Colonel) Theodore Roosevelt, First Volunteer Cavalry, distinguished himself through the action, and on two occasions during the battle when I was an eye-witness, his conduct was most conspicuous and clearly distinguished above other men, as follows:

1. At the base of San Juan, or first hill, there was a strong wire fence, or entanglement, at which the line hesitated under a galling fire, and where the losses were severe. Colonel Roosevelt jumped through the fence and by his enthusiasm, his example and courage succeeded in leading to the crest of the hill a line sufficiently strong to capture it. In this charge the Cavalry Brigade suffered its greatest loss, and the Colonel’s life was placed in extreme jeopardy, owing to the conspicuous position he took in leading the line, and being the first to reach the crest of that hill, while under heavy fire of the enemy at close range.

2. At the extreme advanced position occupied by our lines, Colonel Roosevelt found himself the senior, and under his instructions from General Sumner to hold that position. He displayed the greatest bravery and placed his life in extreme jeopardy by unavoidable exposure to severe fire while adjusting and strengthening the line, placing the men in positions which afforded best protection, etc., etc. His conduct and example steadied the men, and on one occasion by severe but unnecessary measures prevented a small detachment from stampeding to the rear. He displayed the most conspicuous gallantry, courage and coolness, in performing extraordinarily hazardous duty.

Captain A. A. G., U. S. V.
(First Lieutenant Sixth United States Cavalry.)

Washington, D. C.


April 5, 1899.

Assistant Adjutant-General United States Army,
Washington, D. C.
SIR: In compliance with the request, contained in your letter of April 30th, of the Board convened to consider the awarding of brevets, medals of honor, etc., for the Santiago Campaign, that I state any facts, within my knowledge as Adjutant-General of the Brigade in which Colonel Theodore Roosevelt served, to aid the Board in determining, in connection with Colonel Roosevelt’s application for a medal of honor, whether his conduct at Santiago was such as to distinguish him above others, I have the honor to submit the following:

My duties on July 1, 1898, brought me in constant observation of and contact with Colonel Roosevelt from early morning until shortly before the climax of the assault of the Cavalry Division on the San Juan Hill—the so-called Kettle Hill. During this time, while under the enemy’s artillery fire at El Poso, and while on the march from El Poso by the San Juan ford to the point from which his regiment moved to the assault—about two miles, the greater part under fire—Colonel Roosevelt was conspicuous above any others I observed in his regiment in the zealous performance of duty, in total disregard of his personal danger and in his eagerness to meet the enemy. At El Poso, when the enemy opened on that place with artillery fire, a shrapnel bullet grazed and bruised one of Colonel Roosevelt’s wrists. The incident did not lessen his hazardous exposure, but he continued so exposed until he had placed his command under cover. In moving to the assault of San Juan Hill, Colonel Roosevelt was most conspicuously brave, gallant and indifferent to his own safety. He, in the open, led his regiment; no officer could have set a more striking example to his men or displayed greater intrepidity.

Very respectfully,
Your obedient servant,
Colonel United States Army, Superintendent.

December 30, 1898.

Washington, D. C.
SIR: I have the honor to make the following statement relative to the conduct of Colonel Theodore Roosevelt, late First United States Volunteer Cavalry, during the assault upon San Juan Hill, July 1, 1898.

I have already recommended this officer for a medal of honor, which I understand has been denied him, upon the ground that my previous letter was too indefinite. I based my recommendation upon the fact that Colonel Roosevelt, accompanied only by four or five men, led a very desperate and extremely gallant charge on San Juan Hill, thereby setting a splendid example to the troops and 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 supposed, 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, as above stated. The charge in itself was an extremely gallant one, and the example set a most inspiring one to the troops in that part of the line, and while it is perfectly true that everybody finally went up the hill in good style, yet there is no doubt that the magnificent example set by Colonel Roosevelt had a very encouraging effect and had great weight in bringing up the troops behind him. During the assault, Colonel Roosevelt was the first to reach the trenches in his part of the line and killed one of the enemy with his own hand.

I earnestly recommend that the medal be conferred upon Colonel Roosevelt, for I believe that he in every way deserves it, and that his services on the day in question were of great value and of a most distinguished character.

Very respectfully,
Major-General, United States Volunteers.
Commanding Department of Santiago de Cuba.

January 4, 1899.

Washington, D. C.
SIR: I have the honor to recommend that a “Congressional Medal of Honor” be given to Theodore Roosevelt (late Colonel First Volunteer Cavalry), for distinguished conduct and conspicuous bravery in command of his regiment in the charge on San Juan Hill, Cuba, July 1, 1898.

In compliance with G. O. 135, A. G. O. 1898, I enclose my certificate showing my personal knowledge of Colonel Roosevelt’s conduct.

Very respectfully,
Captain Second Cavalry.

I hereby certify that on July 1, 1898, at the battle of San Juan, Cuba, I witnessed Colonel (then Lieutenant-Colonel) Roosevelt, First Volunteer Cavalry, United States of America, mounted, leading his regiment in the charge on San Juan. By his gallantry and strong personality he contributed most materially to the success of the charge of the Cavalry Division up San Juan Hill.

Colonel Roosevelt was among the first to reach the crest of the hill, and his dashing example, his absolute fearlessness and gallant leading rendered his conduct conspicuous and clearly distinguished above other men.

Captain Second Cavalry.
(Late First Lieutenant Ninth Cavalry.)

December 28, 1898.

Washington, D. C.
SIR: Believing that information relating to superior conduct on the part of any of the higher officers who participated in the Spanish-American War (and which information may not have been given) would be appreciated by the Department over which you preside, I have the honor to call your attention to the part borne by Colonel Theodore Roosevelt, of the late First United States Volunteer Cavalry, in the battle of July 1st last. I do this not only because I think you ought to know, but because his regiment as a whole were very proud of his splendid actions that day and believe they call for that most coveted distinction of the American officer, the Medal of Honor. Held in support, he brought his regiment, at exactly the right time, not only up to the line of regulars, but went through them and headed, on horseback, the charge on Kettle Hill; this being done on his own initiative, the regulars as well as his own men following. He then headed the charge on the next hill, both regulars and the First United States Volunteer Cavalry following. He was so near the intrenchments on the second hill, that he shot and killed with a revolver one of the enemy before they broke completely. He then led the cavalry on the chain of hills overlooking Santiago, where he remained in charge of all the cavalry that was at the extreme front for the rest of that day and night. His unhesitating gallantry in taking the initiative against intrenchments lined by men armed with rapid fire guns certainly won him the highest consideration and admiration of all who witnessed his conduct throughout that day.

What I here write I can bear witness to from personally having seen.

Very respectfully,
Major Late First United States Cavalry.

December 25, 1898.

I was Colonel Roosevelt’s orderly at the battle of San Juan Hill, and from that time on until our return to Montauk Point. I was with him all through the fighting, and believe I was the only man who was always with him, though during part of the time Lieutenants Ferguson and Greenwald were also close to him. He led our regiment forward on horseback until he came to the men of the Ninth Cavalry lying down. He led us through these and they got up and joined us. He gave the order to charge on Kettle Hill, and led us on horseback up the hill, both Rough Riders and the Ninth Cavalry. He was the first on the hill, I being very nearly alongside of him. Some Spanish riflemen were coming out of the intrenchments and he killed one with his revolver. He took the men on to the crest of the hill and bade them begin firing on the blockhouse on the hill to our left, the one the infantry were attacking. When he took it, he gave the order to charge, and led the troops on Kettle Hill forward against the blockhouse on our front. He then had charge of all the cavalry on the hills overlooking Santiago, where we afterwards dug our trenches. He had command that afternoon and night, and for the rest of the time commanded our regiment at this point.
Yours very truly,

March 27, 1902.

THEODORE ROOSEVELT, President of the United States.
Washington, D. C.
DEAR SIR: At your request, I send you the following extracts from my diary, and from notes taken on the day of the assault on San Juan. I kept in my pocket a small pad on which incidents were noted daily from the landing until the surrender. On the day of the fight notes were taken just before Grimes fired his first gun, just after the third reply from the enemy—when we were massed in the road about seventy paces from Grimes’ guns, and when I was beginning to get scared and to think I would be killed—at the halt just before you advanced, and under the shelter of the hills in the evening. Each time that notes were taken, the page was put in an envelope addressed to my wife. At the first chance they were mailed to her, and on my arrival in the United States the story of the fight, taken from these notes, was entered in the diary I keep in a book. I make this lengthy explanation that you may see that everything put down was fresh in my memory.

I quote from my diary: “The tension on the men was great. Suddenly a line of men appeared coming from our right. They were advancing through the long grass, deployed as skirmishers and were under fire. At their head, or rather in front of them and leading them, rode Colonel Roosevelt. He was very conspicuous, mounted as he was. The men were the ‘Rough Riders,’ so-called. I heard some one calling to them not to fire into us, and seeing Colonel Carrol, reported to him, and was told to go out and meet them, and caution them as to our position, we being between them and the enemy. I did so, speaking to Colonel Roosevelt. I also told him we were under orders not to advance, and asked him if he had received any orders. He replied that he was going to charge the Spanish trenches. I told this to Colonel Carrol, and to Captain Dimmick, our squadron commander. A few moments after the word passed down that our left (Captain Taylor) was about to charge. Captain McBlain called out, ‘we must go in with those troops; we must support Taylor.’ I called this to Captain Dimmick, and he gave the order to assault.”

“The cheer was taken up and taken up again, on the left, and in the distance it rolled on and on. And so we started. Colonel Roosevelt, of the Rough Riders, started the whole movement on the left, which was the first advance of the assault.”

The following is taken from my notes and was hastily jotted down on the field: “The Rough Riders came in line—Colonel Roosevelt said he would assault—Taylor joined them with his troop—McBlain called to Dimmick, ‘let us go, we must go to support them.’ Dimmick said all right—and so, with no orders, we went in.”

I find many of my notes are illegible from perspiration. My authority for saying Taylor went in with you, “joined with his troop” was the word passed to me and repeated to Captain Dimmick that Taylor was about to charge with you. I could not see his troop. I have not put it in my diary, but in another place I have noted that Colonel Carrol, who was acting as brigade commander, told me to ask you if you had any orders.

I have the honor to be,

Very respectfully,
Your obedient servant,
Captain Twenty-Eighth Infantry,
(formerly of Ninth Cavalry.)

May 11, 1905.

DEAR MR. PRESIDENT: As some discussion has arisen in the public prints regarding the battle of San Juan, Cuba, July 1, 1898, and your personal movements during that day have been the subject of comment, it may not be amiss in me to state some facts coming under my personal observation as Commanding General of the Cavalry Division of which your regiment formed a part. It will, perhaps, be advisable to show first how I came to be in command, in order that my statement may have due weight as an authoritative statement of facts: I was placed in command of the Cavalry Division on the afternoon of June 30th by General Shafter; the assignment was made owing to the severe illness of General Wheeler, who was the permanent commander of said Division. Brigadier General Young, who commanded the Second Cavalry Brigade, of which your regiment—the First Volunteer Cavalry—formed a part, was also very ill, and I found it necessary to relieve him from command and place Colonel Wood, of the Rough Riders, in command of the Brigade; this change placed you in command of your regiment.

The Division moved from its camp on the evening of June 30th, and bivouacked at and about El Poso. I saw you personally in the vicinity of El Poso, about 8 A.M., July 1st. I saw you again on the road leading from El Poso to the San Juan River; you were at the head of your regiment, which was leading the Second Brigade, and immediately behind the rear regiment of the First Brigade. My orders were to turn to the right at San Juan River and take up a line along that stream and try and connect with General Lawton, who was to engage the enemy at El Caney. On reaching the river we came under the fire of the Spanish forces posted on San Juan Ridge and Kettle Hill. The First Brigade was faced to the front in line as soon as it had cleared the road, and the Second Brigade was ordered to pass in rear of the first and face to the front when clear of the First Brigade. This movement was very difficult, owing to the heavy undergrowth, and the regiments became more or less tangled up, but eventually the formation was accomplished, and the Division stood in an irregular line along the San Juan River, the Second Brigade on the right. We were subjected to a heavy fire from the forces on San Juan Ridge and Kettle Hill; our position was untenable, and it became necessary to assault the enemy or fall back. Kettle Hill was immediately in front of the Cavalry, and it was determined to assault that hill. The First Brigade was ordered forward, and the Second Brigade was ordered to support the attack; personally, I accompanied a portion of the Tenth Cavalry, Second Brigade, and the Rough Riders were to the right. This brought your regiment to the right of the house which was at the summit of the hill. Shortly after I reached the crest of the hill you came to me, accompanied, I think, by Captain C. J. Stevens, of the Ninth Cavalry. We were then in a position to see the line of intrenchments along San Juan Ridge, and could see Kent’s Infantry Division engaged on our left, and Hawkins’ assault against Fort San Juan. You asked me for permission to move forward and assault San Juan Ridge. I gave you the order in person to move forward, and I saw you move forward and assault San Juan Ridge with your regiment and portions of the First and Tenth Cavalry belonging to your Brigade. I held a portion of the Second Brigade as a reserve on Kettle Hill, not knowing what force the enemy might have in reserve behind the ridge. The First Brigade also moved forward and assaulted the ridge to the right of Fort San Juan. There was a small lake between Kettle Hill and San Juan Ridge, and in moving forward your command passed to the right of this lake. This brought opposite a house on San Juan Ridge—not Fort San Juan proper, but a frame house surrounded by an earthwork. The enemy lost a number of men at this point, whose bodies lay in the trenches. Later in the day I rode along the line, and, as I recall it, a portion of the Tenth Cavalry was immediately about this house, and your regiment occupied an irregular semi-circular position along the ridge and immediately to the right of the house. You had pickets out to your front; and several hundred yards to your front the Spaniards had a heavy outpost occupying a house, with rifle pits surrounding it. Later in the day, and during the following day, the various regiments forming the Division were rearranged and brought into tactical formation, the First Brigade on the left and immediately to the right of Fort San Juan, and the Second Brigade on the right of the First.

This was the position occupied by the Cavalry Division until the final surrender of the Spanish forces, on July 17, 1898.

In conclusion allow me to say, that I saw you, personally, at about 8 A.M., at El Poso; later, on the road to San Juan River; later, on the summit of Kettle Hill, immediately after its capture by the Cavalry Division. I saw you move forward with your command to assault San Juan Ridge, and I saw you on San Juan Ridge, where we visited your line together, and you explained to me the disposition of your command.

I am, sir, with much respect,
Your obedient servant,
Major-General United States Army.