The Roughest Riders

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Authors: Jerome Tuccille
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Cuba—not the northern coast—where the rebels maintained a strong presence. He assembled a fleet of transport ships beyond a narrow stretch of land bordering the dredged canal in Port Tampa. He then ordered General Shafter to begin shifting men and material along the single nine-mile track connecting the campsites around the city to the ships in the harbor—an ordeal that lasted almost two weeks.
    Roosevelt’s Rough Riders were devastated when they learned that they would have to leave their beloved horses behind, except for six horses per regiment for the officers. On the first sailing, there was only enough room aboard the fleet for essential supplies, pack mules, the small number of horses, and eight troops of seventy men. The allowance for the officers’ baggage was reduced from 250 to 80 pounds. Navy secretary Long, however, convinced the president that such a small armada would easily be destroyed by the Spanish fleet under the command of Vice Admiral Pascual Cervera, which could intercept them before they reached Cuba. Cervera was said to be heading toward Cuba with fresh troops, arms, and supplies.
    The United States’ North Atlantic Squadron, commanded by William T. Sampson, by then promoted to Rear Admiral, was entrusted with blockading the Cuban ports. McKinley countermanded his original instructions and dispatched orders to board the entire expedition simultaneously, triggering a frantic twenty-four-hour rush to get everyone ready to leave as quickly as possible. As it turned out, the transport ships could carry only about sixteen thousand men, rather than the twenty-five thousand authorized for service in Cuba, and Roosevelt was informed he could take with him only 560 of his Rough Riders, roughly half of the men who had signed up. The rest had to remain behind in Tampa. The American fleet was to depart at daybreak on June 8. Anyone not aboard by then would be left behind.
    Roosevelt was furious at the bungled operation, mismanaged from the start before they even got under way. He and his entire group of Rough Riders were in danger of missing out on the action altogether when a train scheduled to pick them up at midnight failed to arrive.
    â€œWe were ordered to be at a certain track with all our baggage at midnight,” Roosevelt wrote, “there to take a train for Port Tampa.” The Rough Riders were there at midnight, but the train never showed up. The men crashed along the sides of the tracks, trying to get some sleep, while Wood, Roosevelt, and a few other officers looked for someone—anyone—with information about what they should do. Every so often they came across a general or two, none of whom knew any more than they did. Other regiments had already boarded trains, only to remain stationary on the tracks when the cars failed to get moving.
    At three o’clock in the morning, Wood got a message telling him to hike his men over to a different set of tracks, where a train would be waiting for them. Again, no such train was in evidence. Finally, at six in the morning, Roosevelt and the Rough Ridersdecided to take matters into their own hands. They commandeered an empty coal train with long flatcars and ordered the engineer to get them on their way to Port Tampa. They simply stopped the train and hopped on board, startling the unsuspecting engineer. Wood and Roosevelt convinced the befuddled gentleman to start backing down the track westward, until they reached the end of the line at the coast in Port Tampa, almost ten miles away.
    Just as daylight was breaking over the eastern horizon, the train chugged into the so-called Last Chance Village, a makeshift town or staging area containing bars, brothels, and women cooking chicken on Cuban clay stoves. The locale was aptly named, as it was the last chance for the men to load up on a decent meal, beer, or whiskey, and a girl if time allowed. Roosevelt and his men were grimy with soot and coal dust, but their entire

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