How was he able to pull these disparate men, regions, and social climes together—westerners and easterners, cowboys and the “swells,” educated and noneducated? To stimulate the “fellow feeling” he believed essential to the success of the mission, he deliberately arranged the tents at the training ground in San Antonio in such a manner that cowboys and wranglers slept side by side with the scions of financiers. He assigned Knickerbocker Club members to wash dishes for a New Mexico company and brought easterners and westerners together in the daily chores of washing laundry and digging and filling in latrines. Eventually, a common denominator emerged throughout the entire regiment—a leveling of money, social status, and education under the aegis of teamwork.
Roosevelt understood from the start that leadership had to be earned; it was not something to be granted by rank or title. The frontiersmen who made up the majority of the regiment were individualists, possessed of a disparaging attitude toward entitlement and hierarchy. As he had learned on the cattle drives in the Dakotas, being the one who issues orders and pays wages was not sufficient to becoming a bona fide boss; he had to lead by sharing his life with the men, by his own willingness to do anything he asked them to do, by never asking them to suffer anything he wouldn’t suffer first. “When we got down to hard pan, we all, officers and men, fared exactly alike as regards both shelter and food,” Roosevelt later wrote. Grumbling ceased “when all alike slept out in the open.”
The crash training course which provided a formidable learning experience for Roosevelt and his men was not without mistakes on his part. He had to learn how to be one with his men without overstepping the line of familiarity to the point of diminishing their respect for him. After a successful day of mock drills in the oppressive heat of San Antonio, he announced to his troops: “The men can go in and drink all the beer they want, which I will pay for!” Later that evening, Colonel Wood summoned Roosevelt to his tent. He described the various disciplinary confusions and dilemmas that inevitably surfaced when an officer relaxed with his recruits. Wood’s admonition was taken to heart: “Sir, I consider myself the damnedest ass within ten miles of the camp.” Chastened, he realized that while he had gained the affection of his troops, he had not established the proper space between himself and his men. “When things got easier I put up my tent and lived a little apart,” Roosevelt recalled, for “it is the greatest possible mistake to seek popularity either by showing weakness or mollycoddling the men. They never respect a commander who does not enforce discipline.” Experience taught him to strike the right balance between affection and respect.
In the boiling chaos of the removal from the drill grounds in Texas to Port Tampa to Cuba, Roosevelt revealed a sure-handed improvisational ability and the administrative initiative to quell confusion, impose order, and skirt protocol to protect his troops. When trains to transport the heavy equipment for his regiment could not be secured, he paid from his own funds. When the canned beef they were fed proved rancid, he demanded and obtained edible provisions. When the boat to convey his men was not available, he occupied another regiment’s assigned boat with a combination of stealth and dispatch. Despite filthy, cramped quarters on board, he imposed inspections and roll calls. In a matter of weeks, he had established the kind of leadership that is bonded by two-way trust. He had taken command of his men by assuming responsibility for them. He had shown his men that he was prepared to do anything he could to provide for them; they, in turn, were prepared to give everything he asked of them.
The master chord of Theodore Roosevelt’s temperament was displayed in the battles and skirmishes of the Rough Riders’ engagement in the Spanish-American War: “Forward to the charge,” “straight ahead,” “charge into the open.” Once the order was set in motion, there was no reverse. “Instead of falling back, they came forward,” one Spanish soldier recalled. “This is not the way to fight, to come closer at every volley.” Yet, even as dozens of men were killed and wounded along the way, Roosevelt, time and again, propelled his troops toward the enemy.
The first battle, at Las Guasimas, began in confusion. As the Rough Riders made their way through the tall grass and twisted brush, they encountered fierce fire from an unseen enemy. Beset by great difficulty, unable to determine what was happening around him, Roosevelt seemed overwrought, jumping “up and down” with tension, bewilderment, and excitement. “What to do next I had not an idea,” he later confessed. When they came upon a cut in a barbed-wire fence indicating the route the Spanish had taken, however, Roosevelt’s uneasiness vanished. Leading his men across the wire, heading straight toward volleys of rifle fire, he suddenly became, according to a witnessing journalist, Edward Marshall, “the most magnificent soldier I have ever seen. It was as if that barbed-wire strand had formed a dividing line in his life.” Leaving indecision behind, Marshall observed, Roosevelt found on the other side of the thicket “the coolness, the calm judgment, the towering heroism which made him, perhaps, the most admired and best beloved of all Americans in Cuba.” Under Roosevelt’s lead, the outnumbered Rough Riders charged uphill and drove back the Spanish soldiers.
What Roosevelt termed the “great day” of his life—the day that ended with the triumphant charges up Kettle Hill and San Juan Hill—began with him exhibiting to the Rough Riders the most placid morning-time demeanor, calmly shaving and knotting a blue polka-dot bandanna around his neck. Rough Rider Arthur Crosby found it heartening “to see our commanding officer on the dawn of a great battle performing an everyday function as though we were on an enjoyable camping trip.” When orders came to march on Kettle Hill while the regulars attacked San Juan Hill, Roosevelt immediately mounted his horse and mustered his men, shouting, “We must advance. Rough Riders forward. Come on.” With Roosevelt in the colonel’s customary position at the rear of the column, the troops advanced hesitantly under a hail of bullets. To inspire his troops to move at an accelerated clip, Roosevelt, the only mounted man, suddenly charged up the lines, rallying his men as he made his way to the front of the regiment. “No one who saw Roosevelt take that ride expected he would finish it alive,” Davis reported. Seated high on his horse with his blue polka-dot bandanna floating “out straight behind his head,” he was “the most conspicuous object in the range of the rifle pits.”
Ascending the hill, Roosevelt’s troops were blocked by another regiment that had not yet received the official order to attack. “If you don’t wish to go forward, let my men pass, please,” Roosevelt addressed the captain. “Up, up they went in the face of death,” one reporter marveled, “men dropping from the ranks at every step. The Rough Riders acted like veterans. It was an inspiring sight and an awful one.” Roosevelt remained erect on his horse all the way, “shouting for his men to follow,” until at last they forced the Spanish to retreat and reached the summit, “cheering and filling the air with cowboy yells.” Within short order, the city of Santiago was captured and the Spanish surrendered.
In newspapers, magazines, and journals across the country, Roosevelt was melodramatically portrayed as the man who “had single-handedly crushed the foe.” Although Roosevelt effusively credited his regiment in multiple military reports and numerous conversations with journalists, carefully citing individuals he felt warranted special recognition, it was the iconic image of the man on horseback, the face so amenable to caricature, that became the emblem of American valor.
“You are the next governor of New York!” reporters shouted at Roosevelt when his regiment arrived at Montauk Point, Long Island. The situation was not so simple, however, as Roosevelt well understood. While he might be the choice of the people at large, the political machine controlled the nomination, and the powerful old boss Thomas Platt had no desire to see a reformer like Theodore in the governor’s chair. In this instance, fate smiled upon Roosevelt. Once again, the Republican Party’s prestige had been besmeared by an exposé of corruption in the current Republican administration in Albany. Believing the hero of San Juan the only candidate who could rescue the party
from defeat, Platt reluctantly agreed to support him for the nomination. On September 15, 1898, the Rough Riders disbanded. Two days later, Theodore Roosevelt entered the governor’s race.
The war veteran who ran for the highest office in New York State was not the same man who had volunteered to fight in Cuba. A more deepseated, durable confidence in his leadership capacities had been earned. “In my regiment,” he told his son, “nine-tenths of the men were better horsemen than I was and two-thirds better shots than I was, while on the average they were certainly hardier and more enduring. Yet after I had them a very short while, they knew, and I knew too, that nobody else could command them as I could.” After the experience of leading his men in combat, earning not only their trust but their devotion, Roosevelt had come to believe that leadership itself constituted the chief of his talents.
Perhaps due in some measure to the heroic image disseminated by the press, the returning colonel projected a newly minted charisma that enabled him to emotionally connect to his audiences. Though candidates in those days rarely campaigned on their own behalf, relying instead on the political machine to whip up voters, Roosevelt “stumped the State up and down and across and zigzag, speaking by day from the end of his special train and at night in mass meetings, in the towns and cities.” He had an aura, one observer noted, “electrical, magnetic.” Audiences discovered “that indefinable ‘something’ which led men to follow him up the bullet-swept hill of San Juan.” Less than three months after returning home, Theodore Roosevelt was elected governor of New York.
Casting an eye over the improbable Cuban Summer, the campaign, and the election, he wrote to a friend, Cecil Spring Rice: “I have played it in bull luck this summer. First, to get into the war; then to get out of it; then, to get elected. I have worked hard all my life, and have never been particularly lucky, but this summer I was lucky, and I am enjoying it to the full. I know perfectly well that the luck will not continue, and it is not necessary that it should. I am more contented to be Governor of New York,” he added, invoking a refrain psychologically necessary to him throughout his career, and always ending with “I shall not care if I never hold another office.”
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Roosevelt’s newfound composure, patience, and maturity were immediately apparent in his adroit handling of the traditional undertow and riptides of New York politics. To reestablish his reputation as a reformer, he had to prove his independence; to get anything accomplished, he had to work with Boss Platt and his political machine. Within days of taking office, he announced that he would make weekly pilgrimages from Albany to New York City to meet with Boss Platt for breakfast or lunch. To reformers who complained that he was belittling “the dignity of the office” by “running down” to confer with the conservative, business-oriented Platt, Roosevelt countered that he had no sympathy for those who found it essential “to preserve their dignity by asserting their right to enter a room first, or to sit on a red instead of a green chair.”
When he was younger, Roosevelt acknowledged, he was too prone to quarrel over trivial matters. The more he read about Abraham Lincoln, the more he valued Lincoln’s willingness to yield lesser issues for more important ones. “No man resolved to make the most of himself, can spare time for personal contention,” Lincoln was wont to say. A conciliatory tone with Platt cost the new governor nothing and could well enhance future endeavors. Moreover, Roosevelt was sensitive to the old man’s pride. Despite the appearance of capitulating to the Boss, he was happy to meet on Platt’s home ground.
In Albany, Roosevelt scheduled every moment of his day with quick military precision, allotting the scores of daily petitioners specific time slots of five or ten minutes. No sooner had the visitor entered the room than the governor jumped up from behind his desk to greet him. “I am delighted to see you,” he began, warmly clasping the visitor’s hand. During these sessions, Roosevelt remained “ever on his feet,” pacing restlessly back and forth, encouraging immediate discussion of “the meat” of the subject. Listening intently, he rapidly absorbed whether he would accede to the request, take it “under advisement,” or regret that he had to say no. Once the decision was rendered, the visitor was gently ushered out of the office with hardly a slack moment before the next visitor entered.
During his tenure as governor, Roosevelt liked to reference an old African proverb: “Speak softly and carry a big stick.” If a leader “continually blusters,” “lacks civility” or likes to quarrel, Roosevelt cautioned, he would not go far. Nor would he succeed by speaking softly if “strength” and “power” did not lay “back of that softness.” As always, a good leader must make it clear that if negotiation fails, as a last resort he would be willing to turn his back and walk away.
Two struggles during his governorship—the fight over a franchise tax and the reappointment of an insurance commissioner with suspected illicit ties to the insurance industry—best illustrate how Roosevelt successfully navigated his contentious relationship with the political machine.
Roosevelt discovered that for decades past the New York legislature had granted exclusive franchises worth tens or even hundreds of millions of dollars to corporations to operate electric street railways, telephone networks, and telegraph lines. Such lucrative franchises were regularly awarded with no attempt to secure tax revenues in return. Recompense came in the form of campaign contributions to fuel the Platt machine—funds which were then distributed to candidates for the state legislature with the “gentlemen’s understanding” they could be counted upon for important votes, particularly those related to corporate interests.
“It was a matter of plain decency” that corporations receiving great benefits from the public should “pay their fair share of the public burden,” the new governor flatly concluded after thoroughly researching the franchise issue. He sent a special message to the legislature indicating his support for a franchise tax bill. The bill’s surprise passage just before the legislature adjourned set off a “storm of protest” from the business world. Overnight, the stock market plunged. Angry corporate representatives descended upon Roosevelt, threatening to move their operations to a more accommodating state. Platt, in a bitter letter, promised an ugly confrontation unless Roosevelt summoned the courage to correct “the big mistake” of his life by declining to sign the bill.
Refusing to be bullied, yet understanding that a break with the machine would be politically fatal, Roosevelt agreed to hold a hearing with corporate representatives in order to solicit suggestions for improvements in the bill. So long as the kernel of the bill remained intact, he considered everything else the husk which he was willing, if necessary, to discard. Persuaded by these conferences that sections of the law were carelessly drawn, he consented to call the legislature back into a special session to modify the bill. If the ultimate product weakened the principle of taxation in any essential way, however, he was fully prepared to restore and sign the original bill. The final legislation both protected the core principle of taxation and made minimal concessions allowing Platt to save face with his constituents in the business community.
Roosevelt’s inclination to “speak softly and carry a big stick” brought an even more troubling dispute with the Republican organization to a desirable outcome. He had heard rumors that Platt’s “right-hand” man, superintendent of insurance Lou Payn, had “intimate” dealings with companies he was assigned to regulate. Roosevelt decided to conduct his own inquiry. Preliminary evidence was sufficient to persuade him that Payn should not be reappointed once his three-year term ended. Platt met Roosevelt’s decision with an “ultimatum”: By law, the incumbent could remain in office until a successor was confirmed. Since the machine controlled the Senate, Platt effectively had the power to veto any replacement the governor chose. The boss made it clear to Roosevelt that he intended to use that power as long as necessary.
“I persistently refused to lose my temper, no matter what he said,” Roosevelt recalled. “I had made up my mind,” he simply explained to
Platt, “that the gentleman in question would not be retained.” To ease the matter, he gave Platt “a list of four good machine men” and told the Boss to select any one of the four. Platt refused to budge. Reformers abused Roosevelt for negotiating at all with Platt. They wanted him to wage open warfare. The impasse dragged on for weeks until further investigation disclosed a $400,000 loan Payn had received from a trust company controlled by an insurance firm under his own jurisdiction. To prevent a scandal, Platt quietly capitulated, agreeing to the nomination of one of the men on Roosevelt’s list.
If he had “yelled and blustered” in public, Roosevelt told a friend, he would not have mustered “ten votes” in the Senate; by the same token, if he had not wielded “the big stick,” the organization would not have gotten behind him. He had preserved his relationship with Platt “by the simple process of telling him the truth, of always letting him know before anyone else when [he] was going to do something that I knew would be disagreeable to him.” Platt respected Roosevelt’s personal candor: “I have ever preferred that a man should tell me face to face that he will or will not do a thing, than to promise to do it and then to not do it.”
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