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  Even when Teedie began studying for Harvard’s entrance examinations, he continued his rigorous exercise regime. “The young man never seemed to know what idleness was,” observed Arthur Cutler, a recent Harvard graduate who had been hired to prepare Teedie for the exams. “Every leisure moment would find the last novel, some English classic or some abstruse book on natural history in his hands.” Working long hours every day, Teedie studied Latin, Greek, literature, history, science, and mathematics, completing in two years what normally took three years of preparation. His ability to concentrate, one contemporary recalled, was such that “the house might fall about his head,” and “he would not be diverted.” When given an assignment, he rarely waited until the last moment. He regarded procrastination as a sin. Preparing ahead, he recognized, freed him from anxiety—a habit of mind that would set an example for his colleagues in the years ahead. Easily passing all eight examinations, he was admitted to Harvard, eager to leave his mark on the world, though not knowing exactly how.

  * * *

  “The story of Theodore Roosevelt,” one biographer has suggested, “is the story of a small boy who read about great men and decided he wanted to be like them.” There is a decided accuracy to this statement; but more than the fictional characters he admired, young Roosevelt found in his own father the most powerful exemplar of the heroic ideal. “My father was the best man I ever knew,” Roosevelt later said. “He combined strength and courage with gentleness, tenderness, and great unselfishness.” He was a public figure of great accomplishment in the philanthropic world, committed to “every social reform movement”; yet, “I never knew any one who got greater joy out of living than did my father.” Roosevelt considered Thee not only “his best and most intimate friend,” but a beloved mentor whose advice he heeded above all others. “It seems perfectly wonderful in looking back over my eighteen years of existence,” he told his family, “to see how I have literally never spent an unhappy day, unless by my own fault!”

  While more than intellectually prepared for his studies at Harvard, Theodore lacked the social skills of many of his fellow students. One classmate remembers him as “studious, ambitious, eccentric—not the sort to appeal at first.” The shelves in his room were filled with dead lizards and stuffed birds. If academic nonchalance was in style, Theodore was strident and zealous, prone to interrupt class in order to barrage professors with objections and questions. He disdained fellow students who drank or smoked, and kept his distance from classmates until he could determine if their families shared his own station in life.

  If young Roosevelt lacked the empathy and kindness that won Lincoln affection wherever he went, his original personality eventually captivated his classmates, who marveled at his irrepressible energy and lack of self-consciousness. Though he “never conquered asthma completely,” suffering spasms at irregular intervals for decades, he had strengthened his body sufficiently so that he could participate in a wide array of sports. He wrestled and sparred, ran three or four miles a day, took up rowing and tennis, and continued to work out in the gym. Though he failed to excel in any of these activities, he derived immense satisfaction from the sheer fact of overcoming his earlier invalidism. While posting honor grades every semester, he organized a whist club and a finance club, joined the rifle club and the arts club, and was elected to the most prestigious social club of all, the Porcellian. Nor did he abandon his interest in birds, tramping miles from Cambridge to observe them, shoot them, and stuff them. In the midst of all this activity, he managed to teach Sunday school and take weekly dance classes. Of course he danced awkwardly—“just as you’d expect him to dance,” a classmate recalled; “he hopped.” His life at Harvard “broadened every interest,” Corinne noted, “and did for him what had hitherto not been done, which was to give him confidence in his relationship with young men of his own age.”

  * * *

  Theodore would need all the confidence he had developed at Harvard to withstand the single greatest sorrow he could possibly have imagined. In December of Theodore’s sophomore year, his forty-six-year-old father fell ill with colon cancer. Earlier that fall, Thee had been nominated by President Rutherford B. Hayes to be collector of customs for the Port of New York, the most powerful federal post beyond the cabinet. Thee’s nomination, which had to be approved by the Senate, was considered a triumph for civil service reformers and a blow to the corrupt politicians who, over the years, had treated the post as a private treasure chest. For weeks, the Senate was consumed by a battle between the reform element of the Republican Party and the machine politicians. The machine element won; Thee’s nomination was turned down. “I fear for your future,” Thee wrote his son. “We cannot stand so corrupt a government for any length of time”—a warning that would long reverberate in young Roosevelt’s mind, helping to shape his embattled style of leadership.

  Thee’s death, three months after his diagnosis, brought Theodore unbearable sorrow. “I felt as if I had been stunned, or as if part of my life had been taken away,” he recorded in his diary. “If it were not for the certainty, that, as he himself has so often said, ‘he is not dead but gone before,’ I should almost perish.” In the days that followed, Theodore filled his diary with thoughts of his father. “Every now and then it seems to me like a hideous dream,” he wrote. “Sometimes when I fully realize my loss I feel as if I should go wild,” for “he was everything to me; my father, companion, friend.”

  “The death of Mr. Roosevelt was a public loss,” stated the New York Times. “Flags flew at half-mast all over the city. Rich and poor followed him to the grave.” As Theodore contemplated his father’s legacy, he began to take the measure of his own life. “Oh, how little worthy I am of such a father,” he wrote in his diary. “How I wish I could ever do something to keep up his name.”

  For Theodore, who had been blessed with a positive temperament, it was only a matter of time before he recovered his spirits. In late June, he confided in his diary the surprising recognition that he was “leading the most intensely happy and healthy out of doors life,” spending his days “riding on horseback, making long tramps through the woods and fields after specimens.” In frenetic movement he found relief as well as an understanding of his fundamental character. “I could not be happier, except at those bitter moments when I realize what I have lost. Father was so invariably cheerful that I feel it would be wrong for me to be gloomy, and besides, fortunately or unfortunately, I am of a very buoyant temper, being a bit of an optimist.”

  “No one but my wife, if ever I marry,” Theodore wrote in his diary, “will ever be able to take [my father’s] place.” The following fall, his junior year at Harvard, he fell in love with Alice Hathaway Lee, the seventeen-year-old daughter of a wealthy Brahmin family in Chestnut Hill, Massachusetts. “It was a real case of love at first sight,” Theodore told a friend, “and my first love too.” With the same single-mindedness he had given to his books, his specimen collections, and the building up of his body, he launched a crusade to make Alice his wife. He escorted her to parties and to dances, took her skating and sledding, on horseback rides over trails and long hikes through the woods. He introduced her to his friends at Harvard and brought her to meet his mother and siblings in New York. He laid siege to her family, playing whist with her parents, entertaining her younger brothers with ghost stories and tales of adventure. He made “everything subordinate to winning her.” He asked her to marry him six months after they met. She turned him down, fearful of taking such a big step at such a young age. Her rejection made him “nearly crazy,” unable to study or sleep at night. He refused to give up, however, and eight months later, “after much pleading,” she finally consented to be his wife. “I am so happy that I dare not trust my own happiness,” he recorded the night she accepted. “I do not believe any man loved a woman more than I love her,” he rejoiced two months later.

  * * *

  Privilege can stunt ambition, just as the lack of privilege can fire ambition. Privilege had no
t hampered the fierce drive that led Theodore to master every activity, from his voracious reading to the creation of the Roosevelt Museum of Natural History, from the rigorous workout regimen he maintained to the intense concentration that produced excellence at every stage of his education. Yet, under the sheltering wing of his father, privilege had allowed him to indulge his wide-ranging interests without the need of practical focus. Thee was the one who had provided his son with his own library, a private gym, a personal trainer, tutors in taxidermy and college preparation, and the means to collect specimens from around the world to fill his personal museum. During his freshman year at Harvard, his father had told him that if he were still committed to becoming a naturalist, he could do so. He explained “that he had made enough money to allow me to take up such a career and do non-remunerative work of value if I intended to do the very best work there was in me; but that I must not dream of taking it up as a dilettante.” That Theodore Roosevelt did not become a naturalist he attributed to the curriculum at Harvard, where biology was treated “as purely a science of the laboratory and the microscope,” ignoring the study of birds, animals, trees, and the outdoor world. For a young man who craved continual motion, who had methodically increased his physical endurance and strength over the years, the idea of a sedentary career, studying tissues under a microscope, held no allure.

  Theodore’s recognition that he was not suited for science revealed a growing self-awareness—a deepening understanding of his own temperamental strengths and weaknesses—that would become an essential tool in his leadership arsenal. Though he abandoned the prospects of a naturalist career, he never stopped pursuing outdoor adventures or his passion for the natural world. In the eighteen months after his father’s death, he went on three expeditions into the deep wilderness regions of Maine, each sojourn further stretching the horizons of his cramped social world and bringing him in close quarters with people whose lives he had encountered only through books.

  The first trip had been arranged through his Harvard tutor. “I want you to take that young fellow under your special care,” Cutler told the Maine guide, Bill Sewall. “He is not very strong and he has got a great deal of ambition and grit. . . . Even if he was tired, he would not tell you so. The first thing you knew he would be down, because he would go until he fell.” Cutler’s assessment proved on the mark. While Theodore suffered from a serious asthma attack during the trip, he never once lost his good nature or seemed “out of sorts,” whether canoeing five miles on the river, tramping thirty-five miles in the forest, helping to pitch the tents, or missing numerous shots at loons, ducks, and pigeons.

  The thirty-four-year-old Maine guide, who would become Roosevelt’s mentor and lifelong friend, was the first to see in the young man the makings of a leader. “He was different from anybody I had ever met,” Sewall said. “Wherever he went, he got right in with the people,” connecting with them, talking with them, enjoying them, without the slightest trace of condescension. The boy who had begun college leery of commingling with lower social echelons now bunked in a lumber camp with a large crew of woodsmen who did not know anything but the woods. “I doubt if they could have written their names,” Sewall recalled. “But they knew the woods, the whole of them, and they knew all the hardships connected with pioneer life.” That young Roosevelt could open himself up to such men, relate to them, and learn from them suggested that in the aftermath of great sorrow he was beginning to chip away at the inherited elitism of his privileged background. He told Sewall he was thrilled to get “firsthand accounts of backwoods life from the men who had lived it and knew what they were talking about.” Even at this early age, Sewall marveled, “he was quick to find the real man in very simple men.” He listened intently to their stories: he told stories himself from the adventure books he had read; he connected with them. He was learning, Sewall said, what it meant to be an American, the idea that “no man is superior, unless it was by merit, and no man is inferior, unless by his demerit.” The profound pleasure Theodore had discovered in a different kind of social life would lead to a reassessment of his future prospects.

  He had thought for a time to follow his father’s footsteps, carrying on the philanthropic work Thee had so successfully undertaken to improve the lot of the poor. “I tried faithfully to do what my father had done,” he told a friend, “but I did it poorly.” After joining “this and that committee” and assuming several board positions formerly held by his father, he found the work uncongenial. He could no more sit in meetings for hours on end than he could sit in a laboratory, staring into a microscope. He concluded that he had “to work in his own way” to carry forward the moral ardor his father had displayed. The noblesse oblige he had inherited from his privileged class felt too removed from the action of life, too indirect. Moreover, he began to suspect that charitable work would be less necessary if the political order provided remedies for the underlying social conditions. “I’m going to try to help the cause of better government in New York City,” he told a friend during his senior year in college; “I don’t know exactly how.” He decided to go to Columbia Law School, not because he wanted to be a lawyer, but because he considered it a first step toward involvement in some aspect of public life.

  He found the courses at law school ill-suited to his temperament, noting critically that the professors were more concerned with “what law is, not what it ought to be,” emphasizing legal precedents rather than justice. In college, he had deliberately stayed away from debating societies, believing it wrong to train young men to “talk glibly” on any given side of a proposition, regardless of their convictions or moral principles. He worried that as a lawyer, he would be required to do precisely that. He wanted to win arguments because they were right, not because he had skillfully marshaled an array of one-sided facts. His energies not fully engaged in his classes, he began spending more and more time at Morton Hall, immersed in the blood sport of working-class politics.

  * * *

  “When I went into politics,” Roosevelt later conceded, “I was not conscious of going in with the purpose to benefit other people but of getting for myself a privilege to which I was entitled in common with other people.” Unlike Lincoln, who held a double ambition from the start (not solely for himself, but also for the people he wanted to lead), twenty-three-year-old Roosevelt intended simply to exercise his right of citizenship, with small consideration toward embarking upon a career. Deploring the “lack of interest in the political questions of the day among respectable, well-educated men, young men especially,” he sought to set an example.

  Who’s the “greenhorn”? the people of New Salem had asked upon first encountering the awkward, poorly dressed, ill-educated Lincoln. “Who’s the dude?” the local politicians inquired upon first seeing young Roosevelt. With his hair parted in the center, short whiskers on his cheeks, a monocle over one eye held in place by “a gold chain over his ear,” a waistcoat and trousers “as tight as a tailor could make them,” he looked the embodiment of a dandy, overly concerned with appearance and manners.

  Yet, for Theodore and young Abraham, once the oddity of first impressions faded, perspectives shifted and people strongly connected with both of them. Week after week, Theodore visited Morton Hall, relaxing with working-class Irish and German immigrants, with butchers, carpenters, and grooms as they drank beer and smoked cigars, listening to their stories, joining them in games of cards, thoroughly enjoying the convivial, masculine atmosphere.

  “I went around often enough to have the men get accustomed to me and to have me get accustomed to them,” he later said, “so that we began to speak the same language and so that each could begin to live down in the other’s mind what Bret Harte has called ‘the defective quality of being a stranger.’ ” In time, the men at Morton Hall recognized they were in the presence of an exceptionally good-natured, earnest, appealing, intelligent young man, who fought for what he believed but accepted defeat with good humor. Watching Roosevelt over a period of months, loca
l boss Joe Murray began to take “a paternal interest” in him, and finally concluded that this twenty-three-year-old son of privilege could make a credible run for the state legislature.

  The time between the November first nomination and the election occupied but a single week, magnifying the vital role of the party organizations in bringing out the vote. To open the campaign, the boss planned to take Roosevelt on “a personal canvass through the saloons along Sixth Avenue.” Saloonkeepers in those days played an instrumental political role, drawing up checklists of the “right” voters in the ward, making sure those voters got to the polls. The first stop was Valentine Young’s bar. No sooner had Roosevelt been introduced to Mr. Young than trouble began. The saloonkeeper told Roosevelt that if he won, he expected him to vote for lowering the cost of the liquor licenses, which were much too high. Roosevelt replied that while he would treat all interests fairly, on the contrary, liquor taxes were “not high enough,” and that he would vote to raise them. The boss swiftly shepherded Roosevelt away, deciding that he and his colleagues would henceforth take care of the Sixth Avenue vote, leaving Roosevelt to solicit votes among his neighbors and friends.

  In the few statements he made, Roosevelt proclaimed that he was “owned by no man” and would enter the legislature “untrammeled and unpledged.” With no sense of irony, he proclaimed that despite his friendship with and key obligations to Joe Murray, he “would obey no boss and serve no clique.” His pledge of independence struck a chord with the residents of the Silk Stocking District, who detested machine politics and rarely bothered to get involved in local elections. The strategy of running as an independent widened Roosevelt’s appeal. Two days after the nomination, a list of twenty prominent New Yorkers, including future secretary of state Elihu Root and Columbia law professor Theodore Dwight, published a vigorous endorsement of young Roosevelt’s candidacy. “We take much pleasure in testifying to our appreciation of his high character,” the manifesto declared. “He is conspicuous for his honesty and integrity.” That same day, Joseph Choate, the future ambassador to Great Britain, organized a circle of Thee’s friends to contribute to Republican campaign coffers. “Men worth millions solicited the votes of their coachmen,” journalist Jacob Riis reported, “and were glad to get them.” On Election Day, the “brownstone vote” came out in much larger numbers than usual. Roosevelt won the Assembly seat with a margin almost twice the size of the typical Republican vote.