Heir to the Empire City

IF BAD WEATHER ON ELECTION DAY favors the underdog, in November 1896 New York Democrats were hoping for a hurricane. Instead they got a beautiful late fall day, the kind New Yorkers savor before the onset of winter. People happily walked or rode carriages to the nearly 1,400 polling places in New York County. Election officers commented on the rush to vote early. Before the polls even opened, voters lined up to cast their ballots, and until noon large crowds could be seen at most polling places. The turnout was enormous. In some city districts, nearly every registered voter cast a ballot. In the Twelfth District, George McClellan Jr., son of the famed Army of the Potomac commander, ran as a Democrat against Charles Hess, brother of Jake Hess, Roosevelt’s old nemesis in the Twenty-First Assembly District. For most New Yorkers, voting took mere seconds. For those voting a straight ticket, only a single box needed to be checked. In addition to the presidential, state, and local elections, a single measure appeared on the ballot, a proposed amendment to the New York State Constitution. Theodore Roosevelt had a keen interest in the outcome of all of these votes.

The proposed amendment had to do with the preservation of the Adirondacks. President Harrison had signed the Forest Reserve Act into law in March 1891, while Roosevelt was civil service commissioner. But Roosevelt’s Boone and Crockett Club had played a key role in the passage of the bill, as it had lobbied Congress, the secretary of the interior, and the White House about the dangers of deforestation and the need for federal action. The act authorized the president to set aside public lands as forest reserves. After signing the bill, Harrison almost immediately set aside 13 million acres of protected forest, all of it in the West. From the beginning, however, Roosevelt had also envisioned protecting the Adirondacks, and a state Adirondack Park was established by Albany the following year. The initial law, though, allowed the state to lease parklands for camps and cottages. Roosevelt and other conservationists championed the “Forever Wild” movement, which opposed allowing any selling or leasing of land set aside as parks or reserves. In 1894, a covenant was added to the state constitution declaring Adirondack Park “forever wild.” Henceforth, any change to the “forever wild” clause would require the approval of a majority of the state’s population and two successive legislatures. Attempts were made to do this in 1895 and 1896. Returning to Oyster Bay to vote in 1896, Roosevelt undoubtedly checked only two boxes: one to vote a straight Republican ticket, and a second to oppose the constitutional amendment allowing campsites in Adirondack Park. The amendment was defeated.

So, too, were the Democrats. While William Jennings Bryan won the solid South and much of the West, he lost to McKinley in those states where Roosevelt had traveled that summer and fall: Minnesota, Michigan, Illinois, and North Dakota, which had become a state in 1889. In New York State and in the city, Republicans scored massive victories. New York’s Republican boss Thomas Platt’s man Frank Black was elected governor with a plurality of more than 200,000 votes. Republicans gained a majority in the state legislature. In the city, for the first time since the organization of the Republican Party in 1856, New Yorkers gave a majority of their votes to the Republican presidential candidate. In New York State, McKinley secured the greatest plurality ever given to any candidate: he beat Bryan by about 270,000 votes, greater even than Cleveland’s record-setting plurality when he was elected governor in 1882. For anyone paying close attention, McKinley’s great electoral victory illustrated how the success of the national ticket could trickle down to state and local elections. In an editorial, the Times noted that the result “has been quite independent of the record of the Republican Party in State affairs and of the character of its candidates.” This was a slap at Platt, and the Republican machine in New York, but it is unlikely Platt much cared what the paper said. Although he was not running for office in 1896, on Election Day Platt emerged as New York’s greatest victor.

Almost immediately, speculation began as to the constitution of McKinley’s new cabinet. New York was the largest and most politically important state in the Union, so at least some of those posts were expected to go to prominent New Yorkers. Early on, top New York Republican Cornelius Bliss was rumored to be under consideration for Treasury, although he ended up at the Department of the Interior. Eventually, New Yorkers John Hay and Elihu Root would find top spots in the McKinley administration. One prominent New York Republican not mentioned amid the speculation was Theodore Roosevelt, who had lobbied hard for a position. He had hosted close McKinley confidant Mrs. Bellamy Storer at Sagamore Hill; had paid homage to this year’s Republican kingmaker, Mark Hanna; had campaigned wherever Hanna and the Republican National Committee had sent him; and had even called on McKinley at his home in Canton, Ohio. Now much hinged on the efforts of Lodge and other prominent Republicans.

Within a month of the election, Lodge visited McKinley in Canton. The visit was likely meant to mend fences with the president-elect. Lodge and Roosevelt had opposed the 1890 McKinley Tariff and McKinley’s 1896 nomination for the presidency. In a two-hour conversation, McKinley touched upon a variety of subjects, including the new Cuban revolution against Spanish colonial rule, tariffs, and possible nominees for secretary of state. Talk then turned to Theodore Roosevelt’s suitability for the Navy Department. Just as Blaine had worried about Roosevelt’s temperament back in 1888, McKinley worried that the police commissioner would have, as Lodge recounted, “preconceived plans which he would wish to drive through the moment he got in.” Lodge reassured McKinley that was not the case, and he pressed a Roosevelt appointment as the one personal favor the president-elect could do the Massachusetts senator. Outside observers assumed that Lodge had gone to Canton to seek an office for himself. Probably no one imagined that such a senior American statesman as Lodge, crafter of America’s new foreign policy as a world power, was pressing the case for a mere New York civil servant.

McKinley was not the only person who needed convincing about Roosevelt’s suitability for the Navy Department. Lodge and Roosevelt still had to contend with Boss Platt. For a decade, Platt had shown his power to block or ease federal actions in New York State. The 1896 elections had only increased his power. By December, Platt was readying for the following month’s Republican state caucus, which would almost unanimously support him for a seat in the US Senate. A week after visiting McKinley, Lodge called Platt on the telephone and asked for his support of Roosevelt for assistant secretary of the navy. The Easy Boss was as coy as ever. Platt told Lodge he worried that from the Navy Department Roosevelt would “make war” on the party organization. Lodge was perplexed. How could an assistant secretary of the navy come into conflict with the Republican state machine? “There is the Brooklyn Navy Yard,” Platt replied. He referred to federal appointments there, but as Lodge pointed out later in a letter to Roosevelt, new rules had made such appointments “perfectly trivial” and under the purview of the navy secretary, not the assistant secretary. Lodge told Roosevelt he thought Platt did not realize that the “matter of Navy Yard patronage died out of the Navy Department some years ago.” But Lodge did not know Platt. Of course Platt knew by heart every position of federal patronage in New York State. Platt used the pretended concern as a smokescreen to keep both Lodge and Roosevelt off balance and under his sway. Such prevaricating was classic Platt, as Roosevelt would soon find out.

Every day Roosevelt must have thanked heaven for a friend like Lodge. The Massachusetts senator secured further support for a Roosevelt appointment from John Hay; McKinley’s new secretary of the interior, Cornelius Bliss; fellow US senators Edward Wolcott of Colorado and Cushman Davis of Minnesota; Speaker of the House Thomas Reed; McKinley’s secretary, John Addison Porter; and even the vice president–elect, Garret Hobart. By March, it was clear that John Long, former governor of Massachusetts, was to be the new navy secretary. Lodge met with Long, who spoke “in the highest terms of you,” as he told Roosevelt. “The only thing resembling criticism was this queer one: ‘Roosevelt has the character, standing, ability and reputation to entitle him to a Cabinet Minister. Is not this job too small for him?’” This was a nice bit of dissembling by Long. Still, Long was not the problem; Platt was still withholding his support. Roosevelt asked a couple of New York machine Republicans to talk to Platt, but he received a depressing response. Platt noted the appointment to McKinley’s cabinet of New Yorkers opposed to the machine, men like Cornelius Bliss. All further appointments, Platt asserted, should therefore go to organization men, and Roosevelt’s appointment would mean, as Lodge wrote to Roosevelt, “one place less for the organization people, to which he could not well consent.” The conversation with the Platt men left Roosevelt temporarily downcast. Within two days, however, he heard from top Platt lieutenants that the machine now favored his appointment. It was enough to give a man whiplash. But Platt’s support made sense, as it was a way to get Roosevelt out of his current job in New York. The turn of events gave Roosevelt pause. He wondered to Lodge whether Platt’s previous opposition “was not merely said with the hope of making me give him something in connection with this office, or else to establish a ground for holding off, so as to get something from the Administration.” Roosevelt was learning.

In April 1897, Roosevelt finally received the much-coveted appointment as assistant secretary of the navy. New York’s reformers received the news of Roosevelt’s imminent departure as they might a death in the family. Charles Parkhurst, who had long called for reform of the New York City Police Department, wrote to Roosevelt, “I consider your departure a municipal affliction” and “a personal bereavement.” Father Alexander P. Doyle, editor of Catholic World magazine, said he felt sorry for the city of New York. “You have planted the standard of municipal honor further ahead and higher up,” he wrote. “I cannot contemplate the loss of your fearless honest spirit to this municipality without some regret.” Even Roosevelt’s Mugwump nemesis E. L. Godkin wrote to say “how very sorry I was to hear of you leaving the New York police.” “In New York,” Godkin added, “you were doing the greatest work of which any American today is capable, and exhibiting to the young men of the country, the spectacle of a very important office administered by a man of high character in the most efficient way.” These were warm sentiments from a man who mocked Roosevelt in his journals. New York reformers saw Roosevelt’s departure from their city as a grave loss.

If Roosevelt had not taken the post in Washington, however, Platt and other Republicans would have likely found some other way to remove him from the police commission, voluntarily or not. After years serving the city—whether in the Assembly, running for mayor, or as police commissioner—Roosevelt was finished with New York City posts. This did not mean New York City no longer served as an important base of Roosevelt’s power, or that his New York City identity diminished in any way. As the geographical considerations of cabinet appointments illustrated, Roosevelt’s “New Yorkness” remained an important political characteristic. In Roosevelt’s future possibly lay more New York positions, perhaps in Congress, or in a statewide position such as governor or US senator.

Returning to Washington presented the Roosevelts with a serious problem. It was expensive. In August, Roosevelt wrote his Uncle Jim that his personal tax “is put on me much heavier than it used to be in New York [City], and I adhere to New York as my place of abode, so I shan’t pay any in Oyster Bay. I have been voting in New York for the past two years, and that has been my residence.” It was an interesting comment from Roosevelt. One important reason he claimed New York as his residence was so that he could vote in the city and affect the outcome of city and state elections. For anyone who has tried to characterize Roosevelt as a kind of “country gentleman” who preferred Oyster Bay to Manhattan, Roosevelt himself made plain that his connection to the city remained important. But it was also costly. Because of this, Roosevelt’s lawyer would eventually suggest a way to reduce the assistant secretary’s tax burden. All Roosevelt had to do was to swear an affidavit repudiating his residence in New York since moving to Washington in April 1897. Roosevelt would do this in March 1898, stating, “Since 1897, I have not had any domicile or residence in New York City.” Although his political opponents would soon make much of this, the importance of such a statement should not be exaggerated. After all, it was not Roosevelt’s idea, and he did it for tax reasons only. Had Roosevelt even imagined that it might disqualify him from any new office, either in the city or in the state, he would not have made such a statement. The affidavit reflected penny-pinching more than any rejection of the city of his birth, the place he constantly referred to as “my city.”

ROOSEVELT’S SINGLE YEAR in the Navy Department was a momentous one. With war with Spain a distinct possibility, and with Secretary Long frequently out of the office, Roosevelt had much latitude in implementing ideas for a larger and more modern navy. He saw Lodge all the time and dined frequently with the president. By September 1897, Roosevelt had developed detailed plans as to the US Navy’s deployment in both the Caribbean off Cuba and the Pacific off the Spanish Empire’s other major holding, the Philippines. For someone so in the thick of things in Washington, his connection to and concerns about New York remained surprisingly strong. He kept up correspondence with New York newspaper editors, such as Paul Dana at the Sun, and continued his public jousting with the Post and the Journal. His friend on the police commission, Avery Andrews, kept Roosevelt abreast of developments in the police force, and in August 1897, he offered his congratulations to the new chief of police. The next month, Roosevelt published, in The Atlantic Monthly, an article entitled “Municipal Administration: The New York Police Force,” in which he defended his enforcement of the Sunday excise law in the face of widespread opposition. It was a nice chance for Roosevelt not only to defend his record, but also to keep his name before New Yorkers. As Lodge had noted during the Sunday excise fight, residents of upstate New York supported the law and Roosevelt’s enforcement of it. By 1897, it was they who would have to vote Roosevelt into any future statewide position.

As of now, Roosevelt was keeping his New York residence in order to play a role in city elections, but the elections of 1897 proved a maddening affair. As assistant secretary of the navy, Roosevelt had the luxury of observing the Republican disaster that autumn from a safe distance in Washington. Indeed, the elections that year probably made Roosevelt doubly happy that he had left behind him the problematic position of president of the New York City Board of Police Commissioners, and New York politics in general.

In 1897, wealthy city reformers made another effort to undermine the power of the machine by founding the independent Citizens’ Union. By running candidates for elected positions in the city, both for mayor and for seats in the state legislature, the Citizens’ Union hoped to separate city politics from the state and national party organizations. This was a direct attack on Platt’s power as Republican boss. That fall, the Citizens’ Union ran former mayor of Brooklyn and Columbia University president Seth Low for mayor of New York City. Since the spring, Platt had called for an alliance of independent and machine Republicans to defeat Tammany Hall, and he approached Low about accepting both the Citizens’ Union and Republican nominations. Low refused. In return, Platt refused to endorse Low.

Right from the beginning, it appeared obvious that Low would simply split the Republican vote and allow the election of a Tammany mayor. A week before Low’s nomination, Roosevelt wrote to Lodge to complain about the “idiotic conduct of the Citizens’ Union.” At the same time, throughout the October campaign Roosevelt continuously reached out to Low and his supporters. After Cornelius Bliss came out publicly for Republican candidate Benjamin Tracy, Roosevelt wrote to Low saying that President McKinley had expressly told him he should not voice his support for Low. “I only wish I could be on the stump for you,” Roosevelt wrote to Low, “for I have hardly ever felt more interested in anyone’s success. All I could do on the quiet has been done.” Apparently this included making his support for Low as widely known as possible among New York acquaintances. Roosevelt indicated his support to Carl Schurz, Jacob Riis, New York financier John Kennedy Todd, publisher George Putnam, and E. L. Godkin. He told Putnam that he had given money to the Citizens’ Union, and indicated to Todd and Schurz that he had contemplated resigning his post to campaign for Low. To friend Lodge, however, he excoriated both Low and the Citizens’ Union. The day after he wrote to Low, Roosevelt told Lodge that he could not “with self respect” support the Citizens’ Union. “I am glad I am out of it,” Roosevelt wrote his friend. Roosevelt and Lodge spent a great quantity of ink tearing down Low and the Citizens’ Union. On October 29, Roosevelt replied to Lodge, agreeing with the senator’s assessment that, in not seeking fusion with the Republicans, “the conduct of the Low people and of Low . . . was not merely stupid, but from the civic standpoint almost criminal.” “What a grim comedy the whole canvass is!” Roosevelt concluded. Roosevelt was hardly laughing.

Democrat Robert A. Van Wyck won the mayoral election handily, with 80,000 more votes than Seth Low, and more than double the votes of Benjamin Tracy. Labor candidate Henry George had died of a stroke during the campaign; his son replaced him on the ballot and finished a distant fourth. Tracy even polled fewer votes than Roosevelt had in 1886, when Brooklyn was still a separate city. Platt and the Low people had achieved pyrrhic victories of a sort. Platt had shown Citizens’ Union supporters that they could not win without regular Republican support, but the Citizens’ Union supporters had shown Platt that they could deny Republicans election in the city. The Citizens’ Union had also managed to deny the Republicans victory in the elections for the state Assembly. Of the city’s thirty-five seats, only two were won by Republicans, as opposed to thirty-one by Democrats. By running independent candidates in city districts as well as for mayor, the Citizens’ Union had secured two of its own seats in the Assembly while ensuring a reduced Republican majority in Albany. It was this outcome that caused Roosevelt to refer to the election results as a “disaster.” “I don’t see much hope in the situation in New York,” the assistant secretary wrote Lodge from Washington. “The Citizens’ Union people are very foolish, and the unspeakable scoundrelism as well as folly of the machine has alienated decent republicans more deeply than you could imagine.” During the campaign, Roosevelt had followed a pattern of publicly reaching out to both wings of the party while privately condemning both. No matter how much he may have criticized Platt, Roosevelt was learning some valuable political tactics from the Easy Boss.

The 1897 elections made a deep impression on Roosevelt. Writing in his 1913 Autobiography, he remembered the results of those elections as having “brought the Republican party to a smash, not only in New York City, but in the State.” Roosevelt had long seen the dangers of a split Republican Party. The 1897 elections proved once again to Roosevelt the absolute necessity of a united Republican Party. As he indicated to Lodge, only fools would advocate otherwise. Platt, too, seemed chastened by the result. He would soon look for a candidate for governor who would be palatable to both machine and reform Republicans.

By early 1898, however, great events were overshadowing New York City politics. Three years after Cubans had once again revolted against Spanish imperial rule, an American war with Spain seemed imminent. Since the birth of the republic, American presidents had tried unsuccessfully to acquire the island of Cuba, a mere ninety miles off the coast of Florida. As Latin American revolutions stripped Spain of its holdings, the once-great empire gripped its only remaining New World colonies—Cuba and Puerto Rico—ever more tightly. This irritated a United States that was growing in both political and economic power—and that was increasingly willing to assert that power in the Western Hemisphere. By the time of the latest Cuban insurrection, Americans had invested $50 million in the island’s sugar fields, while Britain and European powers increasingly bowed to American interests in the hemisphere. A Cuban junta had established offices in New York City and fed propaganda of Spanish atrocities to the yellow press. By 1896, Congress had passed a resolution recognizing the Cuban belligerency. Throughout the country, Americans took up the cry of Cuba Libre!

Under pressure to make some sort of firm gesture toward Spain, and to ensure the safety of American lives and property in Cuba, in January 1898 President McKinley dispatched the battleship Maine to Havana harbor. Early the next month, William Randolph Hearst’s New York Journal published a letter from the Spanish minister to Washington, Enrique Dupuy de Lôme, criticizing McKinley. The De Lôme letter led to the minister’s return to Spain and inflamed American opinion. Worse was yet to come. On February 15, the Maine blew up in Havana harbor, killing more than 250 American sailors. War fever gripped the yellow press and Americans in general. Even as McKinley tried to negotiate Cuban autonomy with Madrid, pressure on the president mounted to ask Congress for a declaration of war. On April 11, McKinley relented. By the end of the month, America was at war.

Roosevelt, Lodge, and others wanted war with Spain not because of any mindless love of war, but to kick the brutal, decrepit, and Catholic Spanish Empire out from America’s hemisphere. Roosevelt did his part by preparing the navy for war, including sending orders to Commodore George Dewey to prepare the Pacific Squadron to move against the Philippines. From New York came unwanted advice. Republican operator Benjamin Tracy, defeated for mayor the previous year, and so close to Platt that he was law partner with Platt’s son Frank, sent both President McKinley and the Navy Department strongly worded suggestions as to the building and deployment of America’s fleet. As secretary of the navy under Benjamin Harrison, Tracy thought he had the right to proffer advice. On April 2, before McKinley asked Congress for a declaration of war, Tracy urged moving the fleet toward St. Thomas. On April 15, as Congress debated declaring war, Tracy wrote again to criticize the navy’s preparations. Why, he asked, were five battleships still under construction? Why had a fleet of “torpedo boats” not been ordered? “Buying yachts and tugs may be well,” he scoffed, “but it is not an adequate provision for a naval conflict, and to longer delay the construction of torpedo boats is little less than criminal.” Roosevelt wrote cordial replies, pointing out his position subordinate to Secretary Long. While still carrying out the business of the Navy Department, Roosevelt was likely distracted by other concerns. Only a week later, it was announced that Roosevelt had resigned his post to become second-in-command of the First US Volunteer Cavalry. Via San Antonio, Texas, and Tampa, Florida, Roosevelt was bound for Cuba.

IN NEW YORK, Katherine Duer was not happy. Although her wedding day was supposed to be the most special day of her life—or so everyone told her—it was not as special as it should have been. Katherine could not complain about the arrangements. Her parents’ house at 17 West 21st Street had been transformed for the occasion. White lilies and apple blossoms formed a grotto at one end of the drawing room, where the ceremony would take place. The mantel above the fireplace had been completely covered with bougainvillea, specially grown for the wedding. Long branches of blooming apple blossoms concealed the doors of the drawing room and the library next door. In the hallway, roses were everywhere, except in the places where there were palms instead, to conceal the orchestra. Neither could Katherine complain about her dress, a simply tailored affair of heavy satin with a long veil. She could even take pride in the fact that she was marrying into royalty. Her husband, Clarence Mackay, although untitled himself, was related by blood to Italian royalty. Attending the ceremony were Mackay’s aunt, the Countess Telfener, and his sister, the Princess Colonna. This made Katherine herself a sort of princess, did it not? Having royalty at her wedding was a great social coup. But so many invited guests and members of the wedding party were conspicuous by their absence. Katherine blamed the war.

A May 17 wedding was considered late in the wedding season, and the Mackay-Duer nuptials were among the very last of the year for their New York social set. Had the ceremony taken place only a week earlier, many of the absent young men would have been able to attend. Craig Wadsworth, a leader of cotillions and a star polo player, was supposed to have been one of Mackay’s ushers. Worse, the best man was supposed to have been Reginald Ronalds, former Yale football star, member of the Knickerbocker Club, and descendant of tobacco magnate Pierre Lorillard. Both members of the wedding party were absent. So, too, were many of the invited guests, young men who were the cream of New York society. Although the elder Tiffanys attended, their son William did not. Hamilton Fish, former Speaker of the Assembly and son of President Grant’s secretary of state, was present. His nephew, also named Hamilton Fish, was not. Only the week before, shortly after the United States declared war on Spain, all the young men had traveled to Washington, DC, where they had been inducted into the army. Almost immediately, they left Washington for training in San Antonio under the leadership of their new lieutenant colonel, a former assistant secretary of the navy and, like them, member of New York’s social elite, Theodore Roosevelt. Instead of attending Katherine Duer’s wedding, Wadsworth, Ronalds, Tiffany, and Fish were all now part of the First US Volunteer Cavalry, a regiment that would soon be known as “The Rough Riders.”

It is often forgotten that Roosevelt initially served as second-in-command to Leonard Wood, a full colonel with battlefield experience. More importantly, Wood had played a key role in some of the last skirmishes with Native Americans in the West, including the capture of Geronimo. As America was preparing for war in April 1898, Wood received the Medal of Honor for his western efforts. His citation reads: “Voluntarily carried dispatches through a region infested with hostile Indians, making a journey of 70 miles in one night and walking 30 miles the next day. Also for several weeks, while in close pursuit of Geronimo’s band and constantly expecting an encounter, commanded a detachment of Infantry, which was then without an officer, and to the command of which he was assigned upon his own request.” Roosevelt is often credited with attracting western cowboys to the regiment, because of his stint in North Dakota, but little credit is given to Wood. However, Wood not only was a combat veteran, army officer, Medal of Honor winner, and famed Indian fighter, but had also served in America’s Southwest, along the border between the United States and Mexico. Most of the cowboys who joined the Rough Riders did not hail from North Dakota. In fact, only three members of Roosevelt’s regiment were listed as being from that state. Instead, they came to Texas by the trainload from the neighboring Arizona, New Mexico, Oklahoma, and Indian Territories. This was where Wood’s name, not Theodore Roosevelt’s, had prominence. It was Wood who detailed men he knew in all of those places as recruiting officers. It was Wood who chose San Antonio as the regiment’s point of assemblage, because it was adjacent to Fort Sam Houston. It was Wood who arranged the purchase of horses in Texas. Finally, it was Wood who left Roosevelt behind in Washington to ensure that the Ordnance and Quartermaster’s departments delivered promised supplies, while Wood established the camp in the State Fair Grounds on the outskirts of San Antonio. Roosevelt was a stranger to Texas and the Territories. In Wood, the Southwest welcomed home a hero.

Theodore Roosevelt’s name still carried much weight in New York, however, and New Yorkers joined the regiment by the score. Aside from Texas, New Mexico, and the Indian Territories, no part of the United States sent more soldiers to the Rough Riders than New York State. Most of these men hailed from the city. There were poor Katherine Duer’s missing wedding guests—Craig Wadsworth, William Tiffany, Hamilton Fish, and Reginald Ronalds. Kenneth Robinson, brother to Roosevelt’s brother-in-law Douglas Robinson, also joined. So, too, did a football star and son of a New York millionaire, I. Townsend Burden Jr. In addition, Woody Kane, only two years behind Roosevelt at Harvard, joined, along with former Princeton football star Horace Devereux. Bob Ferguson, whose brother Ronald was a British member of Parliament, was a close friend of Roosevelt’s from New York; he became a second lieutenant. The list of prominent New Yorkers who joined Roosevelt was lengthy. The Bull brothers, Charles and Henry, had rowed crew at Harvard and were sons of a wealthy New York broker. David M. Goodrich, of the Goodrich rubber family, had captained crew at Harvard and would later become chairman of the B. F. Goodrich Company in Akron, Ohio. Sumner Gerard, like Kenneth Ferguson, was a champion golfer. Dozens more New York men joined, listing as their home addresses houses along Fifth Avenue or various social clubs. They were joined by other prominent young men from Newport, Rhode Island, and New Haven, Connecticut. Four New York City policemen joined, along with Edwin Emerson of Collier’s magazine. New York newspapers identified this local contingent as “College and Club Men,” while others referred to them as “The Fifth Avenue Boys.” They might have been called “The Ritz Riders.”

Young men growing up in Manhattan’s elite society necessarily had much in common with even the roughest of western cowboys. Like Roosevelt, they had learned to ride and shoot, and both Craig Wadsworth and Hamilton Fish were champion polo players. Young men of the Victorian era were expected to be manly and athletic, which is why Roosevelt had taken up boxing and wrestling, promising his father that he would stay fit. Like Roosevelt, a few had even gone west to work on cattle ranches. Basil Ricketts, son of Civil War general James Ricketts, had worked for two years on a ranch in Colorado, as had William Tiffany. They received no special treatment either in camp or in battle. A few were given commissions, but most served as troopers in Troop K, which might be called the “Club Troop.” The elite young men from Manhattan served side-by-side with cowboys and Indians, became friends with them, and died with them. The most dramatic example of this was the short military career of Hamilton Fish.

Fish, who stood six feet two inches, had captained crew at Columbia College. After graduation, he had spent a few years as a man about town before heading west to try his hand at being a cowboy. Roosevelt knew Fish’s uncle well. A longtime Republican member of the Assembly, the elder Hamilton Fish was a former Speaker and a Platt man. And as both Hamilton Fishes were members of the Union Club, it is likely Roosevelt had been acquainted with young Ham Fish before the war. When the call went out for volunteers, Fish eagerly enlisted. He almost did not make it to Cuba. In April 1898, the United States found itself so ill-prepared for war that it did not have enough transports to get its army to Cuba. Fish’s I Troop had been ordered to stay behind at the embarkation point in Tampa. Captain Allyn K. Capron of L Troop asked Colonel Wood if Fish could be transferred to his troop and promoted to sergeant. Fish, then, found a place on a transport to Cuba sporting an extra stripe, but without a horse. Because of the lack of space, the First US Volunteer Cavalry regiment had to leave its horses behind.

Fish became friends with Ed Culver, part Cherokee, who had been raised on the cattle ranges of the Indian Territories. In Cuba on June 23, during a soaking rain, Fish and Culver stood under a tree together trying to stay dry. “Old boy,” said the club man, “this is soldiering.” When the rain stopped, the two made a fire, and Culver made coffee as Fish watched. Colonel Roosevelt and Captain Capron sauntered over. Roosevelt later remembered the moment in his account of the campaign. “As we stood around the flickering blaze that night,” Roosevelt recalled in The Rough Riders, “I caught myself admiring the splendid bodily vigor of Capron and Fish—the captain and the sergeant. Their frames seemed of steel, to withstand all fatigue; they were flushed with health; in their eyes shone high resolve and fiery desire. Two finer types of the fighting man, two better representatives of the American soldier, there were not in the whole army.” Within twenty-four hours, both men would be dead.

The next day, June 24, at Las Guásimas, the Rough Riders came into contact with the Spanish. Culver dropped behind a rock, and Fish crawled up beside him. “Got a good place?” Fish asked. “Yeh,” Culver replied. Fish fired four or five shots before a single Spanish bullet tore through both Fish and Culver. Fish was shot through the heart and died. Culver was also shot through the chest, but he was able to stagger to the rear, one hand clutching the wound as blood soaked the front of his uniform. Later the journalist Richard Harding Davis came across Fish’s body. Reaching into the dead trooper’s clothes, Davis pulled out an expensive watch engraved with the words “God gives.” Roosevelt next passed Fish and stopped a moment to contemplate the young man’s body. It had been a costly skirmish, taking the lives of eight of the Rough Riders. Fish’s military career had lasted only three weeks. Roosevelt called him “one of the best non-commissioned officers we had.”

After the skirmish of Las Guásimas, the Rough Riders settled into camp as the American high command planned the battle that would bring the war to a speedy end. The US Navy had bottled up the Spanish fleet in Santiago Harbor, while Spanish troops occupied the heights above the city. If the Americans could take the heights, they could besiege the city and make continued Spanish occupation of Cuba untenable. Roosevelt and his men were ordered to attack the San Juan Heights on July 1. Just before the battle, Colonel Wood was given command of the brigade, replacing a general felled by yellow fever. This left Colonel Roosevelt in full command of the regiment. In front of the San Juan Heights sat a small hill called Kettle Hill. On Roosevelt’s order, his men charged up the hill, a bullet grazing Roosevelt’s elbow while he shot a Spanish soldier with his revolver. From the top of Kettle Hill, Roosevelt could see American infantry making painstakingly slow progress up the San Juan Heights. Almost on instinct, Roosevelt ran to support the attack, nearly forgetting to issue a command to the men behind him. Roosevelt turned back and shouted, “Forward march!” The Rough Riders ran up the heights as Spanish soldiers deserted their positions at the top. When Roosevelt and his men reached the crest, they could gaze down onto Santiago. Two weeks later, the Santiago garrison surrendered, signaling the end to Spanish power in the Western Hemisphere. With the exploits of Roosevelt and the Rough Riders already making headlines across the country, the Battle of San Juan also signaled the beginning of a new chapter in Roosevelt’s political career. Already, messages were arriving in Cuba asking Roosevelt to run for governor of New York.

For the time being, Colonel Roosevelt was too busy tending to his wounded and sick. New Yorkers continued to figure prominently among the casualties of the war. Ken Robinson, Charles Bull, and Horace Devereux were wounded, and Bob Ferguson and William Tiffany fell ill. Becoming sick with malaria, typhoid, or yellow fever often posed a greater threat to a soldier than a physical wound. Fewer than four hundred American soldiers died in combat during the war, but ten times as many succumbed to disease. William Tiffany contracted yellow fever in Cuba. In August, the transport Olivette delivered him to Boston, where Tiffany checked into the Parker House hotel “in a sadly emaciated condition,” the hotel staff observed. He died the very next day. It was said that his last words were “Colonel Roosevelt is a brick.” Roosevelt attended the funeral in Newport, Rhode Island, riding there on John Jacob Astor’s private yacht.

The Rough Riders departed Cuba on August 8, and after four days’ quarantine aboard ship, on August 15 made camp at Montauk Point on Long Island. The New Yorkers in the regiment took the opportunity to visit home. A sickly Craig Wadsworth stopped by the Knickerbocker Club, the hall porter failing to recognize the sunburned figure wearing a battered army hat and discolored canvas clothes. On Sunday, August 21, the Reverend Henry Brown, chaplain of the Rough Riders, gave the sermon at Grace Episcopal Church, declaring the men “more respectful of religion than any other regiment.” Roosevelt’s camp attracted visitors, too. President McKinley came, accompanied by Vice President Garret Hobart, Secretary of War Russell Alger, and Attorney General John Griggs. Considering Roosevelt’s future career, perhaps the most important visitor to Montauk Point was Lemuel Quigg. Republican boss Thomas Platt had sent his lieutenant to sound out Roosevelt about running for governor of New York.

DID THEODORE ROOSEVELT’S heroism in Cuba make him governor of New York? Roosevelt himself certainly thought so. Later, as president, as he traveled through North Dakota with naturalist John Burroughs, Roosevelt commented that had he not raised the regiment of Rough Riders and gone to war, he would not have been made governor of New York—and that it was becoming governor of New York that made his rise to the presidency almost inevitable. Burroughs rightly observed that Roosevelt “would have got there someday,” but perhaps it would not have been quite as quickly without the war with Spain. Roosevelt was not nominated for governor in a vacuum, however. Nearly twenty years of public service in New York, Albany, and Washington had made him a well-known figure in the Empire State well before the Rough Riders set foot on Cuban soil. And, although it is natural to focus on Roosevelt’s dramatic actions as a soldier during the war, the war should not distract attention from political events closer to home that played a role in his election. Roosevelt’s nomination was not in his own hands, or even in the hands of New York voters. It is better to ask another question: Did Roosevelt’s Cuban actions gain him the support of Republican boss Thomas Platt? The answer is no.

Almost as soon as McKinley won the White House in 1896, Platt had worried about the Republican Party losing support among independents. An ominous sign came when independent Republicans in New York backed Joseph Choate for the US Senate seat sought by Platt in early 1897. With US senators still chosen by state legislatures, and with an enormous Republican majority in Albany after the 1896 elections, Platt won election easily, but the independent bolt continued. The November 1897 New York City elections proved a stunning blow to Platt and a catastrophe for the Republicans. From Washington, Theodore Roosevelt had watched as Platt refused to back Seth Low for mayor, and the split among anti-Tammany forces allowed the election of a Democrat as the first mayor of Greater New York. In the large cities outside of New York, the picture was equally grim. Albany, Binghamton, Syracuse, Rochester, and Buffalo all elected Democratic mayors. In the New York Assembly, Democrats nearly doubled their seats from the year before, an increase from 38 to 68. Throughout New York, politicians of all stripes blamed Platt. “There’s a hot time in the old State tonight,” Senator David Hill telegraphed New York’s new mayor, Alton Parker. Top Republican and editor of the New York Tribune Whitelaw Reid said, “Platt’s ‘leadership’ is a costly handicap to the Republican party.” Madison Grant, a Wall Street lawyer, wrote Roosevelt at the time, “We are all stunned here by the catastrophe which has overwhelmed us, but a few of us are emerging from the debris with the determination to cut Mr. Platt’s throat for his share.” Platt said nothing, and contemporary observers noted that he seemed depressed for months, “loaded with the consciousness,” New York Congressman De Alva S. Alexander said, “of being solely responsible for the overwhelming defeat of his party.” Alexander also observed, “The belief existed that his subsequent acquiescence in Roosevelt’s nomination for Governor sourced in an unwillingness to chance the repetition of such another disaster.” The elections of 1897, then, had more to do with Roosevelt’s rise to the governorship than the war of 1898 did.

Although 1898 found Platt still chief of the party, and also a US senator, the problems continued for the Easy Boss. His man in the governor’s mansion, Frank Black, had further alienated independents by his adoption of, in his words, “starchless”—in other words, more flexible, and under the sway of the party machine—civil service that swept out of the state bureaucracy nearly all Democratic officeholders. This action received the condemnation of Roosevelt’s friends in the New York Civil Service Reform Association. The tide continued to turn against Republicans in the 1898 spring town elections for supervisors. In twenty-five counties, Democrats elected seventy-five supervisors, including in Platt’s own hometown of Oswego, where a Democrat had not been elected town supervisor for years. With 1898 an important state election year, Platt could not ignore the signs. In his autobiography he later wrote, “Independent threats caused me to do a heap of thinking. Cognizant of the revolts which . . . deprived Blaine of the Presidency and placed the National and State governments in the custody of the Democrats for eight years and ten years respectively, I began to formulate plans for holding our enemies in leash.” His own lieutenants must have prompted much of this thinking. Benjamin Odell, who had just become the new chairman of the Republican State Committee, actually wrote to Roosevelt about the possibility of running for governor—without Platt’s knowledge—while Roosevelt was still in Cuba. Odell and Quigg pestered Platt about backing Roosevelt’s nomination until Platt finally relented and sent Quigg to meet with Roosevelt at Montauk Point.

The conversation between Roosevelt and Quigg, who was acting as the mouthpiece for Platt and the Republican state machine, reveals much about why Roosevelt received the nomination. Little was said about Roosevelt’s heroism during the Cuban campaign, although that was certainly icing on the cake for placing Roosevelt before New York voters. Mainly, Quigg and Roosevelt spoke about Roosevelt’s close association with the Republican Party and his ability to unite machine and reform Republicans. A dozen years after Roosevelt’s nomination for New York mayor in 1886, Republicans still saw in him a candidate able to bridge the divide between the two factions of the party.

When Quigg visited Roosevelt, Platt was still trying to get Governor Black to withdraw as a candidate for renomination in favor of Roosevelt. Black replied by tearing into Roosevelt, calling him “impulsive and erratic” and likely to “play devil with the organization.” Quigg wrote to Roosevelt saying that Platt’s reply was that “you have always been a sturdy thoroughgoing Republican, and that while you have not identified yourself with the machine, you have never done anything to its injury; that you have promised to act in all important matter [sic] after full consultation and in view of the interests of the organization as such, as well as the party and public interest.” For Quigg and Platt, Roosevelt’s Republicanism was more important than his Cuban heroism.

Right from the beginning, however, the machine politicians understood the pitfalls of having Roosevelt as governor. If a popular figure such as Roosevelt could unite the party behind him, what would stop Roosevelt from challenging Platt for the leadership of the state Republican Party? In other words, Roosevelt’s very success in carrying out Platt’s goals of party unity would pose a direct threat to Platt. Quigg worked hard to dissuade Colonel Roosevelt from becoming enmeshed in “Mugwump”—independent Republican—schemes, and from seeking to become a figure greater than Platt. Roosevelt needed to persuade Platt that he would not seek to displace him as the state party leader and that he would work with the Easy Boss for a united party and strong organization. Quigg’s long September 10, 1898, letter to Roosevelt was almost like a contract between the Colonel and the Easy Boss. Roosevelt wanted the nomination and agreed. As would so many letters from Quigg, Odell, and Platt over the next two years, the September 10 letter ended with a summons to Platt’s offices in the Fifth Avenue Hotel in New York. There, as much as in Albany, lay the real power of the state Republican Party.