This was not the first military service of Roosevelt. Soon after his graduation from Harvard he had joined the Eighth Regiment, New York National Guard, and had been in time promoted to the captaincy of a company. He remained a militiaman for four years, leaving his command only when he took up his permanent residence in Washington as a member of the civil-service commission.
The transports carrying the army of invasion to Cuba sailed from Port Tampa June 13, 1898. Thirty large vessels carried the troops and took six days to reach Daiquiri, the little port to the east of the harbor of Santiago, where the army was disembarked. The Rough Riders were in the brigade commanded by General S. B. M. Young, together with the First (white) and Tenth (colored) Regular Cavalry Regiments, and was a part of the division commanded by General Joseph Wheeler.
The first fight of the Rough Riders took place in the advance from Daiquiri toward Santiago. They were sent out on a hill trail to attack the position of the Spaniards, who blocked the road to the town. The Spanish occupied ridges opposite to those along which the trail used by the Rough Riders led, and a fierce fight took place in the jungle. The Spanish had smokeless powder, and it was almost impossible to locate them in the underbrush. The Rough Riders behaved with great gallantry, and took the position occupied by the enemy, but not without considerable loss. For distinguished gallantry in this action, Lieutenant-Colonel Roosevelt was promoted to be Colonel July 11, 1898. The place of this engagement is called Las Guasimas, “the thorns,” from the large number of trees of that species found there. The Rough Riders in this action acted in concert with other attacking forces composing the vanguard of the army. Several days after this General Young was taken with fever, and Colonel Wood, taking command of the brigade, Colonel Roosevelt became commanding officer of the regiment.
In this capacity he commanded the Rough Riders in the battle of San Juan, where they withstood a heavy fire for a long time, and finally, when ordered to advance, made a gallant charge, capturing two of the hills occupied by the enemy. The fall of Santiago followed the American success, and a period of inactivity began for the American troops. Insufficient transportation had entailed improper and insufficient food, and, together with the effects of the climate, began to have serious effects on the troops. Fever decimated their ranks, and those who were still able to attend to their duties were weakened by disease.
It soon became apparent to the officers in command of the Americans that the only salvation for their men was removal to the North. It had been reported that yellow fever was epidemic among the soldiers in camp about Santiago, and while this was not at all true, most of the men were suffering from malarial fever, and there was some fear of the introduction of the tropic scourge into the United States if the troops were brought home suffering from it.
Colonel Roosevelt was in command of the brigade at this time, owing to General Wood having been made Governor-General of Santiago, and as such the commander of the Rough Riders discussed with the other Generals an appeal to the authorities to remove the troops back to the United States. There was disinclination on the part of the regular officers to take the initiative, as much correspondence had taken place between General Shafter and the War Department, the latter stating the reasons why it seemed inexpedient to cause the removal at that time. In this emergency Colonel Roosevelt prepared a presentation of the situation, and, after reading over the rough draft to the other commanders, submitted it to General Shafter.
Directly afterward a circular letter was prepared and signed by all the Generals and commanding officers and presented to General Shafter. This came to be known as “the round robin,” and its result was instantaneous. Both letters, Colonel Roosevelt’s and the round robin, were published throughout the United States and created a profound sensation. Within three days after they had been delivered to General Shafter the order for the return of the army was issued.
The Rough Riders, with their Colonel, returned to Camp Wikoff, at the northern extremity of Long Island, in late August, and on September 15, 1898, were mustered out of service with Colonel Roosevelt.
The campaign for the control of New York State in the approaching election of a Governor had already begun when the Rough Riders returned from Cuba. Colonel Roosevelt’s name had often been mentioned for the Republican nomination and the popular enthusiasm for this selection was supported by the leaders of the party in the state. Governor Frank S. Black had been elected by an enormous plurality two years previously, and according to all traditions should have been renominated. He was set aside, however, for the new hero, and the convention at Saratoga nominated Colonel Roosevelt with a hurrah. The friends of Governor Black had fought bitterly so long as there seemed a chance of success, and they started the rumor that Colonel Roosevelt was ineligible for the nomination, as he had relinquished his residence in New York when he went to Washington to enter the Navy Department.
The actual campaign was a most picturesque one. B. B. Odell, chairman of the state committee and now Governor of New York, was opposed to Colonel Roosevelt stumping the state in his own behalf, but it soon became apparent that general apathy existed, and consent was reluctantly given to the candidate to do so. There followed a series of speeches that woke up the voters. Colonel Roosevelt, by nature forceful, direct, and theatrical in his manner and method, went back and forward, up and down New York, accompanied by a few of his Rough Riders in their uniforms. These cowboys made speeches, telling, usually, how much they thought of their Colonel, and the tour met with success. Colonel Roosevelt was elected Governor over Augustus Van Wyck, the Democratic candidate, by a plurality of about 17,000 votes.