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  When it came, the call to service was tailor-made for Roosevelt. President McKinley asked for 135,000 volunteers to increase the strength of the Army, then numbering 28,000 men. But the volunteers were to include three regiments “to be composed exclusively of frontiersmen,” recruiting materials specified, “possessing special qualifications as horsemen and marksmen.” Roosevelt, setting his ambitions aside, nominated his friend Leonard Wood, a military hero, surgeon, Medal of Honor winner, and outdoorsman to act as their leader. Roosevelt said he would serve as lieutenant colonel under Wood. And so the Rough Riders were born.

  Applications flooded in – 23,000 of them, enough to man a division. While Wood handled the paperwork and left Washington to establish a training camp near San Antonio, Texas, Roosevelt directed the recruiting of what newspapers called “Teddy’s Terrors,” “Teddy’s Cowboys Contingent,” and “Teddy’s Gilded Gang.” As he let it be known he disliked his nickname, the label gradually became “Roosevelt’s Rough Riders.”

  The regiment immediately drew the attention of the press – and Roosevelt courted reporters. Richard Harding Davis, war correspondent, novelist, playwright, and editor of Harper’s, saw the Rough Riders as the war’s most promising story. “Nothing they have they deny us,” Davis wrote his brother. “Being with such a fine lot of fellows is a great pleasure.” Whatever happened during the conflict with Spain, Roosevelt made sure the world would hear about it.

  The most difficult part of training in Texas was teaching the cowboys – and their horses – to maneuver in formation. But when they got to Tampa, the jumping-off port for Cuba, there wasn’t enough ammunition and supplies for the troops. Only eight of the twelve Rough Rider troops could go, and only the officers could take their horses. Wood and Roosevelt had to decide which men to leave behind. Some wept on receiving the news they would not go into combat. Even so, when he noticed two photographers standing on the pier with a tripod and camera, intending to “take moving pictures of the war,” Roosevelt found room for them.

  The expedition was focused on Santiago, on the southeast tip of Cuba, where Spanish forces were concentrated, and a Spanish fleet was contained by a U.S. Navy blockade. After landing at the coastal village of Daiquiri, the invading army – some 16,000 strong – was to march to Siboney, seven miles along the coast, and from there along the Camino Real to Santiago. Roosevelt and his men knew they would face resistance, particularly as they crossed the San Juan heights into the valley where Santiago nestled.

  The landing was chaotic; one of Roosevelt’s two horses drowned in the surf. The Rough Riders were under the command of Major General Joseph Wheeler, known as Fighting Joe, a Confederate Civil War veteran with a reputation of “never staying still in one place long enough for the Almighty to put a finger on him.” Ignoring orders to stay in Siboney and supervise the landing of the U.S. troops, Wheeler marched ahead of the advance guard along the Camino Real and conducted a reconnaissance of the first line of Spanish defense, some four miles north of the village. Wood, Roosevelt, and the Rough Riders caught up with him there and camped in a coconut grove.

  Shortly before dawn on June 24, 1898, Wheeler set off to meet the waiting enemy at a pass called Las Guasimas. Some 470 soldiers under the command of Brigadier General Samuel Baldwin Marks Young marched north along the road to Santiago, while Wood led 500 Rough Riders along a parallel trail through the woods a half-mile west of the road. The two units would meet at the pass.

  Captain Allyn Capron and Sergeant Hamilton Fish rode point for the Rough Riders. “Their frames seemed of steel, to withstand all fatigue,” Roosevelt wrote. “In their eyes shone high resolve and fiery desire.” Wood and Roosevelt followed, Wood with three aides and Roosevelt trailed by his favorite reporters, Davis and Marshal. Then Spanish snipers opened fire with high-speed Mauser rifles, a withering barrage that killed both Capron and Fish.

  It was Roosevelt’s long-awaited baptism by gunfire, and his men had been wondering how he would take it. He had been a popular officer, acknowledged over Wood as leader of the regiment, but he was impetuous, which led some to question his ability to lead in combat. Now Wood told Roosevelt to take a group of soldiers and circle to the right while Wood took another left. Marshall, a seasoned war correspondent, recorded what happened next: “Perhaps a dozen of Roosevelt’s men had passed into the thicket before he did. Then he stepped across the wire himself, and from that instant, became the most magnificent soldier I have ever seen. It was as if that barbed-wire strand had formed a dividing line in his life and that when he stepped across it he left behind him in the bridle path all those unadmirable and conspicuous traits which have so often caused him to be justly criticized in civic life, and found on the other side of it, in that Cuban thicket, the coolness, the calm judgment, the towering heroism, which made him, perhaps, the most admired and best beloved of all Americans in Cuba.”

  Crawling ahead of his men, Roosevelt returned to the road. Young’s troops were pinned down by Spanish snipers, who were firing from a nearby ridge. Coming to the edge of the jungle, the Rough Riders opened fire on the snipers. The Spaniards soon abandoned their foxholes and retreated into the jungle higher up the ridge.

  By driving back the Spanish front line, Roosevelt opened the way for Young’s troops to attack. Soon the entire American line, with Roosevelt commanding the left, Wood the center, and Young the right, was sweeping up the valley, under orders from Fighting Joe Wheeler. Fifteen hundred Spanish troops began retreating. “We’ve got the damn Yankees on the run!” yelled Fighting Joe, losing track of which war he was fighting. After two hours, the battle of Las Guasimas was over. Sixteen American soldiers died, and fifty-two were wounded.

  Roosevelt’s next battle was to feed his men. Their supplies of hardtack, bacon, and coffee had been eaten or discarded in the heat of the march, and the landing of supplies from the convoy was so disorganized that no food was expected inland for several days. Roosevelt heard there was a supply of beans on the beach and found 1,100 pounds of them at the commissary. But when he tried to get them for his men, the commissar showed him a regulation saying beans were only for officers. Roosevelt stepped outside for a moment, then went back in and demanded the beans.

  “Your officers cannot eat 1,100 pounds of beans,” the commissar told him.

  “You don’t know what appetites my officers have,” Roosevelt assured him.

  “I’ll have to send the requisition to Washington,” said the commissar.

  “All right, only give me the beans.”

  “I’m afraid they’ll take it out of your salary,” the commissar warned.

  “That will be all right,” said Roosevelt. “Only give me the beans.”

  He carried one sack of beans eight miles back to camp, and the Rough Riders had a feast.

  Spanish forces were still entrenched along the San Juan Heights, and it took six days until the American commanding general, Brigadier General William Rufus Shafter, loaded his 300 pounds onto the Army’s strongest mule and climbed a nearby hill to inspect the prospective battlefield. From the basin below, the Camino Real climbed west up the ridge to the pass leading to Santiago. Along the ridgeline, entrenchments and gun emplacements comprised the Spaniards’ last line of defense. To the south of the road - and dominating it - was a blockhouse on San Juan Hill. To the north, short of the ridgeline, was a smaller hill, also heavily fortified. Farther north and east was a more distant hill, the well-defended village of El Caney.

  Shafter’s plan was straightforward. At dawn, Brigadier General H. W. Lawton would take his Second Infantry Division to El Caney and capture it. Meanwhile, Wheeler’s cavalry and Brigadier General J. F. Kent’s First Infantry Division would launch an attack on San Juan Hill, with Lawton reinforcing them on his return from El Caney. Just as at Las Guasimas, the day would end with a massive assault on the heights and a rout of the Spaniards.

  Then Wheeler and Young became ill. Brigadier General Samuel S. Sumner was put in charge of Wheeler’s cavalry. Wood took charge
of Young’s Second Brigade, and a delighted Roosevelt was given command of the Rough Riders.

  July 1 dawned with an exchange of gunfire as the men struggled along the muddy road through 100-degree heat to their assigned positions. Steady gunfire to the northeast indicated that Lawton was having more trouble than expected in his attack on El Caney.

  Roosevelt’s orders were to fan out to the north of the road and establish the Rough Riders at the base of the small hill, Kettle Hill, in front of the heights. It was heavily fortified, and the Rough Riders were taking fire from snipers on its crest. He wanted to drive them off, but he was being held in reserve and could only wait, fuming.

  There was a pause; Sumner was waiting for Shafter’s order to advance, but Shafter assumed anyone leading a charge would know what to do when it was time. Morale was sinking, and casualties were rising. By afternoon, Kent’s infantry worked its way up the lower reaches of San Juan Hill. After sending plea after plea for permission to attack Kettle Hill, Roosevelt finally received what he interpreted as the go-ahead. “The instant I received the order I sprang on my horse,” he wrote, “and then my ‘crowded hour’ began.”

  Roosevelt set off in the colonel’s customary position, at the rear of the column. But as the Rough Riders trudged into a hail of bullets and slowed down, he spurred his horse to the front and barked at his men to follow. He reached the head of the column a short distance from the Spanish lines.

  “No one who saw Roosevelt take that ride expected he would finish it alive,” Davis wrote, but watching him “charging the rifle-pits at a gallop and quite alone made you feel that you would like to cheer. He wore on his sombrero a blue polka-dot handkerchief . . . which, as he advanced, floated out straight behind his head, like a guidon.” Galvanized by Roosevelt’s charge, the Rough Riders stormed the hill, and the Spaniards retreated.

  Davis’ dispatch, which ran in newspapers and magazines across the United States, made Roosevelt the hero of the day and Kettle Hill the center of the action, and that version of the battle endured. For years, the troops who had fought at least as well – particularly the Buffalo Soldiers, black troops in three segregated regiments – were bitter at the way the press, then history, ignored their role.

  Roosevelt’s recollections of the charge are a series of confused impressions. He remembered the sound of his voice, rasping and swearing to get his men to follow him; the sight of a man at his feet, felled by a bullet meant for him; lines of his men parting before his advance; his horse stopped by a roll of barbed wire, and himself wriggling through and running; firing a revolver, and a Spanish soldier doubling over “neatly as a jackrabbit.” He stood at the summit until U.S. troops swarmed up behind them. By most accounts, the first man at the top was a black sergeant of the 10th Infantry Regiment, but Roosevelt’s memory of the moment was indelible.

  When he caught his breath, Roosevelt had a view of the battlefield from the top of Kettle Hill. Kent’s troops were still toiling up San Juan Hill, some 700 yards across the valley, and needed help. Roosevelt spent ten minutes directing fire at the blockhouse on San Juan Hill. Then, as Kent’s men began their final charge, he led the Rough Riders to join them. Most of his men didn’t hear his first command to follow him, and he found himself leading a charge of five men; he had to run back to collect the rest. Pounding down Kettle Hill, they swarmed across the bottom land and up the grassy slopes. The Spanish troops were abandoning their posts, melting into the jungle, and all along the crest of the San Juan Heights, American soldiers were looking down at Santiago.

  The siege of Santiago lasted two weeks until Shafter worked out a face-saving way for the Spanish to surrender: The American guns would bombard the city, but shooting into the air above the houses, and the defenders would hand in their arms, able to say they had capitulated under fire.

  By this point, American troops were coming down with malaria, and an epidemic of yellow fever seemed inevitable. Roosevelt sent men to Santiago to buy “simple delicacies” to supplement their Army rations; by one account, he spent $5,000 of his money to build up his men’s strength. But he was full of vigor, insisting one day on swimming in the Caribbean and ignoring a school of sharks swimming alongside. “They won’t bite,” he assured a man swimming with him. “I never heard of one bothering a swimmer. It’s all poppycock.” The sharks left him alone.

  By this time, almost the entire invasion force was ill or wounded, while Washington ignored pleas to bring the men home. Finally, Roosevelt was drafted to write a letter, signed by his fellow officers, arguing the Army was weak and should return to the United States to forestall “the unnecessary loss of many thousands of lives.” McKinley and officials at the War Department were furious, but within three days, Shafter’s army was on its way to Montauk, Long Island.

  Edith was waiting on the dock when the ship carrying the Rough Riders nudged the pier at noon on August 15, 1898. As the troops disembarked – many limping, many on stretchers, those not wounded stricken with malaria or yellow fever – the assembled reporters noted Roosevelt was “the picture of health,” the only man on the ship who “gave no evidence of having passed through the tortures of the Cuban campaign.”

  “I’m in a disgracefully healthy condition,” he told them. “I feel ashamed of myself when I look at the poor fellows I brought with me.” Then he paused and summed up his war. It had been a time of fulfillment, proof he was the man of action and courage he always wanted to be. He said, “I’ve had a bully time and a bully fight. I feel as big and strong as a bull moose. I wish you all could have been with us.”

  Roosevelt’s boots had hardly touched the pier at Montauk before he was repeatedly told he would be the next governor of New York after the oncoming election, five months away. “Should I run?” he asked Lincoln Steffens. Steffens told him yes and said he would win.

  Both men knew the race would be complicated. The nomination was controlled by Senator Thomas Collier Platt, the undisputed leader of the state’s Republican Party. Platt’s label as the “easy boss” belied his ruthless treatment of anyone who opposed him. Platt had collided with Roosevelt both when the would-be governor was civil-service commissioner, and Platt was trying to preserve patronage jobs, and when he was police commissioner and Platt was protecting his cronies.

  If Platt let Roosevelt become governor, the two would clash over the candidate’s reform principles and growing revulsion at the abuses of robber barons, who provided the money that funded Platt’s power. But Roosevelt was the hero of San Juan Hill and the most famous man in America; given the GOP nomination, he could sweep the state. His chances looked so good that Roosevelt considered an offer to run on an independent ticket, gambling that Platt would have to offer him the GOP nomination as well. In the end, he rejected that tactic, reasoning that he would need the party’s backing to work with the legislature after he was elected.

  After a series of delicate negotiations, Roosevelt showed up in mid-September at Platt’s headquarters in the Fifth Avenue Hotel. Emerging from a long meeting, he started to say, “I had a very pleasant conversation.” Then a reporter shouted, “Will you accept the nomination for governor?” “Of course I will!” said Roosevelt. “What do you think I am here for?” What’s more, he said, he would not accept an independent nomination.

  The independents felt betrayed, reformers suspected a deal had been struck, and Democrats exclaimed the hero had surrendered to the boss. “Rough Rider Roosevelt made a charge up the backstairs of the Fifth Avenue Hotel,” said a Democratic newspaper, but this time, “he was taken prisoner.” The next day, after a long private talk with Roosevelt, Steffens reported in his Commercial Advertiser that there had been no deal. Roosevelt, he said, made the decision on his own to make sure he would have a majority in the legislature to carry out his program.

  That account didn’t reassure everyone, and the campaign got off to a difficult start, with many of Roosevelt’s allies remaining silent. Candidates in those days rarely stumped for themselves, but Roosevelt saw it a
s a viable strategy – and so, in the end, did Platt. In the final weeks, Roosevelt’s campaign train crossed the state, and he attracted large crowds at every stop. “The fire and school bells rang,” said The New York Times. “Cannon fired and a band played, while the people cheered.” Two Rough Riders Accompanied Roosevelt. In an effort to be discreet, they wore civilian clothes, but the people who gathered to see the candidate were eager to hear their stories of Roosevelt’s courage. Sergeant Buck Taylor of Cripple Creek, Colorado, gave this endorsement: “I want to talk to you about mah Colonel. He kept ev’ry promise he made to us and he will to you . . . . He told us we might meet wounds and death and we done it, but he was thar in the midst of us, and when it came to the great day he led us up San Juan Hill like sheep to the slaughter and so he will lead you.”

  This, Roosevelt said later, “hardly seemed a tribute to my military skill, but it delighted the crowd, and as far as I could tell did me nothing but good.” The Roosevelt campaign train chugged on. The candidate delivered as many as nineteen speeches a day and often made impromptu comments at whistle-stops.

  Roosevelt won the election by just 18,000 votes – far short of a landslide, but a triumph for his party. Even Boss Platt conceded that only Roosevelt could have won the race.

  The new governor was forty years old when he took office on a bright January day so cold the band’s brass instruments were frozen and unplayable. Edith was settling the family into the forty-room governor’s mansion in Albany. She hired a governess for fifteen-year-old Alice; enrolled Theodore Jr., twelve, and Kermit, ten, in a local boy’s academy; set up a schoolroom in the basement for Ethel and Archie, ages eight and five; and a nursery for Quentin, still a toddler. Edith dreaded the social obligations that came with her new role as a governor’s wife, but she welcomed the financial security that came with the office. In addition to the mansion, the governor’s job brought a salary of $10,000, and Roosevelt’s celebrity ensured increasing sales for his writing; his forthcoming memoir, The Rough Riders, was set to be serialized at $1,000 per installment. As time passed, Edith made friends and began to enjoy state politics, especially meeting New Yorkers at county fairs and village meetings.