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  Nearly a century after his death, President Theodore Roosevelt is still a vivid presence in America. He was a sickly boy who willed himself to become an outdoorsman and a warrior; a man of letters who remembered everything he read and wrote forty books of his own; a dedicated political reformer who understood that compromise is the key to progress; and a fighter who relished every battle, from leading his Rough Riders in the Battle of San Juan Hill in Cuba to facing down political bosses and busting malevolent trusts that threatened his country. And Roosevelt is widely regarded as one of America’s greatest presidents, whose spectacled face glares from Mount Rushmore in the exalted company of presidents Washington, Jefferson, and Lincoln.

  But beneath that common impression lurks a complex man of contradictions and surprisingly flexible principles, who knew when to fight and when to walk away. He was universally known as “Teddy,” but he came to dislike the nickname, and few of his friends actually used it. He adored his first wife, but after her death, he never spoke her name. He promised a “square deal” for every American, rich or poor, and supported women’s rights, but he never shook his belief that people of other races were incapable of governing themselves without white supervision.

  Roosevelt’s image as one of America’s most straightforward political figures is nearly a caricature of virility, patriotism, devotion to family, and love of nature. More than anything else, what gleams through the dust of history is his zest for life and power; the one word most firmly linked to him is the archaic plaudit, “Bully!”

  THEODORE ROOSEVELT WAS born on October 27, 1858, the second of four children, to one of the wealthiest men in New York City. His father, also Theodore, was a glass merchant and philanthropist who spent his time and money improving the lives of New York’s poorest residents, especially immigrants. Thee, as he was called, had married Martha Stewart Bulloch, nicknamed Mittie, who had grown up on a plantation in the village of Roswell, Georgia.

  Theodore Junior, known as Teedie, was a sickly child, plagued from birth by numerous ailments, the worst of them asthma. When he couldn’t sleep, gripped by an attack, gasping for breath, and terrified he would suffocate, his father would carry the boy from room to room or drive him in his horse and carriage through the city streets. “My father,” Roosevelt would write, “he got me breath, he got me lungs, strength – life.” As Roosevelt’s sister Corinne would say, it was ironic that “Theodore Roosevelt, whose name later became the synonym of virile health and vigor, was a fragile, patient sufferer in those early days of the nursery.”

  Teedie’s comfortable life in Manhattan with his siblings – his older sister Anna, nicknamed Bamie, Elliott (who later became the father of Eleanor Roosevelt, who would marry another more distant cousin, President Franklin Delano Roosevelt.), and Corinne - was disrupted by the Civil War, which strained their parents’ otherwise loving marriage. Mittie’s sister Anna and widowed mother had left Georgia and moved in with Thee and Mittie, and the women’s pro-Confederacy stance conflicted with Thee’s pro-Union sentiments. To avoid arguments, Mittie stayed away from the dinner table. Thee wanted to enlist in the Army, but Mittie argued that he would be fighting against her brothers, so he hired a substitute – then a common practice, but an act he always regretted and one his son would feel honor-bound to redeem. Instead, Thee spent the war years working for the U.S. Sanitary Commission, the forerunner of the American Red Cross, helping sick and wounded soldiers, and the U.S. Employment Bureau, searching for work for soldiers who had lost limbs. He also was a charter member of the Union League, which raised money to support both causes. He worked hard at his business and other philanthropies and enjoyed a rich social life. “Father was the finest man I ever knew and the happiest,” Roosevelt wrote.

  Mittie’s sister tutored the children at home, and Thee instilled in them an abiding love of learning by reading to them, organizing amateur dramas, and encouraging them to write, recite poetry, and pursue other intellectual interests. Teedie was a voracious reader and showed a talent for naturalism; in the family’s summer house at Oyster Bay on Long Island, he watched birds, took lessons in taxidermy, and after obtaining a seal’s head at a local market with two cousins, set up at the age of seven his own Roosevelt Museum of Natural History. Corinne’s friends Edith Carow and Fannie Smith were regular visitors, and Teedie, the ordained leader of the group, orchestrated their activities and made up stories to entertain the other children.

  When Teedie was ten, Thee and Mittie took all the children on a year-long tour of England, France, Germany, Holland, Italy, Scotland, and Switzerland. Teedie kept a detailed diary of his experiences both physical and intellectual, from climbing Mount Vesuvius to viewing the treasures of the Vatican. Despite these adventures, Teedie spent much of the journey bedridden by asthma and stomach troubles. Back home, Thee took his son aside for a talk.

  “Theodore,” he said, using the boy’s formal name to stress the gravity of what he was about to say, “you have the mind but you have not the body, and without the help of the body, the mind cannot go as far as it should. You must make your body. It is hard drudgery to make one’s body, but I know you will do it.”

  Teedie promised, “I’ll make my body.” From then on, he followed a punishing routine of lifting weights and exercising. His father installed a home gym on the second floor of the townhouse, and Teedie’s determination kept him at the task daily, even though his progress was painfully slow. After two boys teased him into a fight and then whipped him “with easy contempt,” as he later wrote, Teedie started taking boxing lessons. Although timid by nature, “by acting as if I was not afraid, I gradually ceased to be afraid.” Courage was a matter of habit and willpower, he decided, and he cultivated it for the rest of his life. It was years before the boxing lessons and the workouts produced visible results, but his health improved; the asthma attacks still came, but rarely. In the month of August 1871, his diary didn’t mention a single ailment. It would be many years before the asthma and intestinal inflammation completely ended, but Roosevelt had conquered his body – and he would do so again and again.

  When Theodore was fourteen, Thee once more took the family abroad, this time spending a year in Egypt, Germany, Greece, Palestine, Syria, and Turkey. The boy reveled in the exotic and historic sights and scenes, writing in his diary: “In the evening, we visited Harnak [sic] by moonlight. It was not beautiful only, it was grand, magnificent, and awe-inspiring. It seemed to take me back thousands of years, to the time of the Pharohs [sic] and to inspire thoughts which can never be spoken, a glimpse of the ineffable, of the unutterable.” He observed, shot, and stuffed dozens of birds and animals, his vision and aim improved by eyeglasses. “I had no idea how beautiful the world was,” he wrote later, “until I got those spectacles.”

  The family returned home to a new mansion on West 57th Street, with a full gym and attic space for Theodore’s specimens. At fifteen, his education was too spotty to qualify him for admission to Harvard, so Thee hired a tutor, Arthur Cutler. Cutler was impressed with “the alert, vigorous character of young Roosevelt’s mind,” writing later, “The young man never seemed to know what idleness was.” His disciplined work took him through three years of college preparation in twenty-four months. He was a hard act for his younger brother Elliott to follow. “Oh, Father will you ever think me a ‘noble boy,’” Elliott once wrote from school. “You are right about Teedie. He is one, and no mistake a boy I would give a good deal to be like.” He promised to “try to be as good . . . but it is hard.”

  At seventeen, Roosevelt passed Harvard’s entrance exam and moved to Cambridge, Massachusetts.

  He was a misfit – “a slender nervous young man with side-whiskers, eyeglasses, and bright red cheeks,” as he put it, and poorly equipped for social contacts. His room teemed
with stuffed animals and birds; the smell of formaldehyde trailed him around the campus. He also was something of a snob, not wanting to get close to his classmates until he made sure their social status was up to Roosevelt standards.

  His classmates called him “bumptious,” “crazy,” a “spluttery” nonstop talker with a squeaky voice, and “a bundle of eccentricities,” but they were fond of him. He was a fount of information on nearly every subject. In time, he became popular.

  Roosevelt ended his freshman year with honor grades in five of seven subjects. Along with his studies, he attended boxing, wrestling, and dancing classes. He taught Sunday school, organized a whist club, joined a poetry-reading group, and chastely courted the girls of Boston at balls, matinees, and theater parties. He discovered too much liquor made him “fighty,” and took care for the rest of his life to drink moderately. Previously careless about his clothing, he became something of a dandy, agonizing over the cut of his coat and complaining about the washerwoman’s treatment of his white cravats.

  Despite his father’s liberalism, Roosevelt had imbibed the political and economic conservatism of his class. He sided instinctively with money and privilege, dismissing the poor as those who had “failed in life.” He denounced the nascent labor movement as socialistic and even anarchistic, and he resisted any limits on the rights of property owners and employers.

  After his freshman year in the summer of 1877, Roosevelt went to observe and hunt birds in the mountains of New York. When he returned to Harvard for his sophomore year, he enrolled in classes in botany and comparative anatomy and decided to become a naturalist.

  But soon after the Christmas break, Roosevelt’s father, “the finest man I ever knew,” died of colon cancer. Summoned to New York, Theodore arrived too late to say goodbye. The death plunged him into a three-month period of grief. “Like a fledgling shoved too soon from the bough,” biographer Edmund Morris wrote, “he tumbled nakedly through the air; some of his diary entries are not so much expressions of sorrow as squawks of fright . . . For month after month, he pours a flood of anguish into his diary, though his letters remain determinedly cheerful.” As he would do all his life, Roosevelt turned to work as therapy. With the arrival of spring, he was surprised to be thinking “pleasant” thoughts about his father. Roosevelt finished the year with six honor grades out of eight. “He distinctly belonged,” one of his professors wrote, “to the best twenty-five in a very brilliant class.” In the end, he graduated twenty-first in a class of 230 students.

  FROM HIS BOYHOOD, Roosevelt had maintained an intense friendship with Edith Carow, Corinne’s friend. The daughter of a shipping magnate, Edith was a frequent visitor both in New York and at the Roosevelt summer home, where the two played, rowed around Oyster Bay, read, and recited poetry to each other. In the summer before his freshman year, Roosevelt’s attentions to Edith had been obvious. At fifteen, she was a quiet beauty with a keen mind, and the family assumed there was an understanding between them. But in the summer of his sophomore year, it came to an end.

  Theodore sent Edith flowers on her seventeenth birthday, August 9. A week later, she arrived for her annual visit to Oyster Bay. The two spent two weeks rowing, picnicking, and gathering flowers. On August 22, they went sailing and then to a family party. “Afterward,” Roosevelt wrote in his diary, “Edith and I went up to the summer house.” Neither of them ever said what happened there, but the diary has no further mention of Edith for several months.

  Back at Harvard, Roosevelt joined the Porcellian Club, the school’s most prestigious society. Through a classmate, he met Alice Hathaway Lee, the daughter of Boston banker George Cabot Lee, and was smitten. “It was a real case of love at first sight – and my first love, too,” he wrote. He pursued her with ferocious determination. The demure, blue-eyed, golden-haired, seventeen-year-old Alice was by all accounts as charming as she was beautiful, and Roosevelt besieged her with long walks, skating and sledding expeditions, and invitations to dances and college functions.

  Although Roosevelt wasn’t conventionally handsome or the stereotypical beau, Alice found him intriguing, amusing, and full of surprises. Still, she refused his first marriage proposal. Theodore was undaunted. He saw her as the object of a scripted pursuit, and her own inclinations were almost irrelevant. “See that girl?” he said to a friend at a party. “I am going to marry her. She won’t have me, but I am going to have her!”

  Several times, he thought he had lost her. But in January 1880, she accepted his proposal. “I am so happy that I dare not trust in my own happiness,” Roosevelt wrote in his diary. “The aim of my whole life shall be to make her happy and to shield her and guard her from every trial; and, oh, how I shall cherish my sweet queen! How she, so pure and sweet and beautiful, can think of marrying me, I cannot understand, but I praise and thank God it is so.” For his friends, there was a somewhat different account. “The little witch led me a dance before she surrendered, I can tell you,” he wrote his cousin John. They were married on his twenty-second birthday, October 27, 1880.

  Roosevelt’s plan to be a naturalist had been deterred by his father’s death and an inheritance that, while generous, wouldn’t underwrite a lavish lifestyle on a scholar’s paycheck. His professor of political economy, J. Lawrence Laughlin, had told him there was more need for bright young men in government than in zoology. The prospect of marriage completed the change of plans, and Roosevelt resolved to study law at Columbia Law School.

  “Our intense happiness is too sacred to be written about,” Roosevelt wrote in his diary during the honeymoon at Oyster Bay. Afterwards, he and Alice moved in with Mittie at the mansion on 57th Street, and he began his law studies.

  In law school, Roosevelt reprised his Harvard performance, peppering professors with questions and arguing fiercely “for justice and against legalism.” The doctrine of caveat emptor, “let the buyer beware,” which largely protected sellers from liability for defective goods, enraged him; the law, he said, should encourage deals “which are fair and of benefit to both sides.” Most of his fellow students admired his quick mind, but it was plain to them that the intricacies of the law were not Roosevelt’s strong suit.

  In the summer of 1881, Roosevelt took Alice to Europe, referring to her in his diary as “the best traveling companion I have ever known,” and observing that she had “a far keener appreciation” of artistic treasures than he did.

  In New York, as he continued to study law, he worked on writing a book, The Naval War of 1812, while escorting Alice through the homes and parties of New York society. “Alice is universally and greatly admired,” Roosevelt wrote, “and she seems to grow more beautiful day by day.” A friend described a typical scene in the Roosevelt household: Teddy standing on one leg beside his bookcase, sketching a diagram for his book, when Alice rushes in, saying, “We’re dining out in twenty minutes, and Teddy’s drawing little ships.” It was Roosevelt’s ideal life, with every moment filled.

  IN THE UPPER-CLASS New York of the 1880s, a gentleman who took an interest in politics had to approach the matter delicately. Campaigning was seen as an unsavory business. A gentleman was instead encouraged to become a lawyer, cultivate relationships with wealthy men, and after a decent interval, could expect to receive a nomination for a seat in the United States Senate. In those days, state legislatures elected senators, and the lawmakers would vote as their moneyed patrons dictated.

  The Roosevelt clan was horrified when Theodore began spending evenings in cavernous, dingy Morton Hall, headquarters of the Twenty-First District Republican Association, the city’s only reliably Republican territory. Known as the Silk Stocking district, there was nothing remotely genteel about the storefronts of East Fifty-Ninth Street or its denizens.

  At twenty-two years old, Roosevelt had decided that real political power could be found only among the men his relatives described as rough and brutal and crass. “I intended to be one of the governing class,” he wrote in his autobiography, “and if they proved to be too h
ard-bit for me, I supposed I would have to quit, but that I certainly would not quit until I had made the effort and found out whether I really was too weak to hold my own in the rough and tumble.”

  Bounding up the stairs of Morton Hall in his evening clothes, Roosevelt seemed out of place among the spittoons, poker tables, and rough-hewn benches, the air thick with smoke from cheap cigars. “He looked like a dude, side-whiskers an’ all, y’know,” one of the ward members told an interviewer years later. But Roosevelt persisted. “As a friend of mine picturesquely phrased it, I ‘had to break into the organization with a jimmy,’” he wrote. “I went around there often enough to have the men get accustomed to me and to have me get accustomed to them, so that we began to speak the same language, and so that each could begin to live down what Bret Harte has called ‘the defective moral quality of being a stranger.’”

  It wasn’t long before his boundless energy, curiosity, and compassion won him a reputation as a fearless advocate. He soon rose to the executive committee of the district’s Young Republicans and garnered attention by backing an unpopular Street Cleaning Bill. When a canny local politician, Joe Murray, used Roosevelt to dethrone the district boss by engineering Roosevelt’s nomination to New York State’s Assembly to replace a tainted incumbent, Murray became the new boss, and Roosevelt’s political career was launched.

  In that first campaign, Roosevelt was still a political naïf. When Murray took him a block away from his Fifth-Avenue roots to campaign among the Sixth-Avenue saloon-keepers and one of them complained that liquor licenses were too expensive, the candidate told him the fees should be raised, not lowered. Ending the conversation, Murray sent Roosevelt straight back to Fifth Avenue. Nevertheless, Roosevelt’s appeal to the Fifth-Avenue swells and the city’s newspapers guaranteed his election, and in January 1881, he postponed law school and began his political education in the New York legislature in Albany.