Shafter, under intense pressure from Washington to depart for Santiago, did not have the transports necessary to move his entire force. He therefore ordered Wood to dismount his cavalry and to select eight out of his 12 companies for the invasion. Roosevelt and Brodie were selected to command the two squadrons in Cuba.

On June 14, after even more high command bungling and mismanagement, the 578-man Rough Rider contingent finally departed from Tampa Bay aboard the Yucatan. ‘We are just like amateurs at war,’ correspondent Richard Harding Davis noted acidly.

Amateurs or not, they were off to change the course of history. Colonel Wood noted ‘that this is the first great expedition our country has ever sent overseas and marks the commencement of a new era in our relations with the world.’ For the men, however, there was little thought of world politics, just much card playing and even an occasional chorus of the Rough Rider’s adopted theme song — ‘There’ll Be a Hot Time in the Old Town Tonight.’

Roosevelt, who often shared the ship’s railing with Buckey O’Neill, was surprised to find that the two-gun Arizona lawman was also ‘a visionary, an articulate emotionalist.’ Under the starlit sky they contemplated the odds against them, with O’Neill expressing a soaring ambition tempered by a dark fatalism. ‘He had taken so many chances when death lay on the hazard,’ T.R. noted, ‘that he felt the odds now were against him.’ Some years before O’Neill had written a short story containing an eerily prescient passage: ‘Death was the black horse that came some day into every man’s camp, and no matter when that day came a brave man should be booted and spurred and ready to ride him out.’

The soldiers reached their destination near Santiago, Cuba, in five days and General Shafter, after conferring with Admiral William Sampson and Cuban rebel leader Calixto Garcia, decided to land his troops at Daiquir and then march inland to Siboney and finally Santiago. Daiquir was supposedly undefended, with a broad beach and even an old wooden pier built by an American iron company years before. On June 22 the troops began to land. They were fortunate to face no opposition, yet the landing was a fiasco. Since there was no transport for the horses and mules, they were lowered by sling into the water and released, or simply pushed off the ships into the sea to swim ashore. Mercifully, by afternoon the Rough Riders were all ashore, although the landings continued into the night.

Shafter promptly ordered General Lawton to occupy Siboney with his infantry division and Wheeler’s dismounted cavalry. Just after dusk on June 23, Wood and Roosevelt entered Siboney. They found Joe Wheeler, ‘a regular gamecock’ as T.R. characterized him, anxious to conduct an armed reconnaissance toward Santiago in hopes of finding the Spanish rearguard. Cuban rebels had spotted enemy troops entrenched a few miles to the north at Las Guasims.

Wheeler moved out at dawn on the 24th with more than 900 men, including all eight Rough Rider companies and 400 men from the regular First and Tenth regiments. The Cubans estimated the Spanish force ahead at 600, but it proved to be three times that number. Moving across unfamiliar terrain against a force of unknown size was dangerous work for seasoned regulars, much less untested volunteers. Wheeler led his regulars down the main road while the Rough Riders traversed a narrow trail to the left. The heat was oppressive in the thick and tangled jungle.

Some three miles from Siboney, a group of Rough Riders led by Captain Allyn Capron and Sergeant Hamilton Fish made contact with the still unseen enemy. As the bullets of the Spaniards’ Mauser rifles whined about them, Capron’s men fanned out, briskly returning fire with their .30 caliber Krag-Jorgensen carbines. Wood and Roosevelt had wisely procured these guns for the unit as replacements for the older, black powder Springfield rifles other volunteers had received. Now the Rough Rider commanders hurried their men forward, deploying them on both sides of the trail.

Cherokee Rough Rider Tom Isbell drew first blood for the Americans, dropping a Spanish sniper just as he received the first of seven wounds — which he somehow survived. Sergeant Fish and Private Ed Culver were also hit at almost the same time. Fish asked Culver, ‘You all right?’ then slumped over, dead. Captain Capron rushed forward to Fish’s body, killing two Spaniards as he advanced before being mortally wounded himself.

Wood calmly led his men forward, taking cover and firing and then advancing again. The Spanish, still well hidden in the jungle, began to melt away before the pressure. Caught up in the excitement of the moment, newspaper correspondent Edward Marshall joined in the combat. The deadly humming of the 7mm Mauser slugs filled the air, like ‘a nasty, malicious little noise,’ wrote Marshall. Within moments he was wounded by a bullet near his spine. Adjutant Tom Hall, witnessing this from afar, mistook Marshall for Wood, and fled to the rear where he reported the colonel dead and the Rough Riders routed. He was later allowed to quietly resign.

Major Brodie was hit in the arm and went down. Six-foot-six Color Sergeant Albert Wright was grazed three times. Captain James McClintock took a bullet in the leg and also fell. Still the Rough Riders advanced, with Roosevelt taking command of Brodie’s squadron as well as his own. O’Neill’s volunteers now joined up with a unit of regulars, and the Spanish began to pull back. With a whoop Captain Robert Huston’s troops opened fire on a group of panic-stricken, fleeing Spaniards. ‘Don’t shoot at retreating men,’ Wood angrily shouted. He ordered the men forward to occupy a deserted, ramshackle building. Black troopers of the Ninth Cavalry now moved up to reinforce the Rough Riders, but the battle was over.

Roosevelt walked the corpse-littered field with Buckey O’Neill. The Rough Riders had lost eight killed and 31 wounded. ‘Colonel,’ O’Neill asked, ‘isn’t it Whitman who said of the vultures that `they pluck the eyes of princes and tear the flesh of kings?’ ‘ Roosevelt, still a bit stunned by the scene, could not recall but later remembered it to be Ezekial: ‘Ye shall eat the flesh of the mighty and drink the blood of the princes of the earth.’

Generals Shafter and Lawton were angry with Wheeler for bringing on an engagement — or walking into an ambush, as many of the regular officers thought. Ambush or not, the Rough Riders had fought their way through, driving a superior force of entrenched infantry from a vital strategic point on the road to Santiago. For six days Shafter kept his men encamped along that road while more supplies and troops came ashore and the road up from the beach was improved.

Already men were dropping in great numbers with fevers, General Wheeler among them. Brigadier General Samuel Sumner took temporary command of the cavalry, with Wood taking over the second brigade. Roosevelt now became colonel of the Rough Riders. Shafter, himself ill, needed to act quickly before sickness further reduced his army. From El Pozo, a commanding hill about five miles east of Santiago, Shafter could easily see the Spanish entrenchments on the San Juan Heights, about a mile and a half away and rising some 125 feet above the valley. A blockhouse stood on the highest of these crests — San Juan Hill — while to its right lay another hill topped with ranch buildings and several old sugar cane cauldrons. It was promptly dubbed Kettle Hill. Between the two heights was a small valley and a pond. Roughly four miles to the north was the Spanish strongpoint of El Caney. Between El Pozo and the San Juan Heights flowed the San Juan River.

Shafter decided to attack on July 1. General Lawton’s Second Infantry Division would assault El Caney. Following Lawton’s success, a force of roughly 8,000 men was to charge the San Juan Heights. Shafter had apparently learned little since the Civil War, when it took a good soldier at least 20 seconds to load and fire his single-shot rifled musket. The entrenched Spaniards could fire eight shots from their 7mm Mausers in the same amount of time. If Major General Arsenio Linares y Pombo’s units had any automatic weapons, the American frontal assault would turn into a bloodbath.

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