The Last Romantic


By H. W. Brands

Read by Matt Kugler

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From the New York Times bestselling author, an acclaimed biography of President Teddy Roosevelt

Lauded as “a rip-roaring life” (Wall Street Journal), TR is a magisterial biography of Theodore Roosevelt by bestselling author H.W. Brands. In his time, there was no more popular national figure than Roosevelt. It was not just the energy he brought to every political office he held or his unshakable moral convictions that made him so popular, or even his status as a bonafide war hero. Most important, Theodore Roosevelt was loved by the people because this scion of a privileged New York family loved America and Americans.

And yet, according to Brands, if we look at the private Roosevelt without blinders, we see a man whose great public strengths hid enormous personal deficiencies; he was uncompromising, self-involved, and a highly imperfect brother, husband, and father.

Beautifully written, and powerfully moved by its subject, TR is the classic biography of one of America’s greatest and most complex leaders.


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Part One



A Child of the Civil War


Like all children, he believed that his home and family occupied the center of the universe; his gradual realization that they didn’t occupy even the center of his native city would be a primary factor in driving him into public life. To be sure, the Roosevelts were respected, not least for their long lineage. The first van Rosenvelt had arrived two centuries earlier from Holland, at a time when the village of New Amsterdam was still Dutch. But the quiet village that had greeted old Claes was now a raucous city, and the solid Dutch burghers, among whom Claes’s descendants had taken their solid place, had been elbowed aside by the English, the Germans, and lately the Irish. In the 1850s, New York throbbed with some eight hundred thousand souls, not counting the additional quarter million in the separate city of Brooklyn across the East River and the nearly one hundred thousand in Newark and Jersey City across the Hudson. Weekly, thousands more poured down the gangplanks of immigrant ships from Europe. Although New York was by far the largest city in America and nearly the oldest, the unceasing torrent of new arrivals gave it a frontier feeling. Nothing lasted; everything was constantly being remade. “Overturn, overturn, overturn! is the maxim of New York,” complained one lifelong resident who ached for a modicum of stability. “The very bones of our ancestors are not permitted to lie quiet a quarter of a century, and one generation of men seem studious to remove all relics of those who precede them.” But most New Yorkers thrived on the changes for the same reason that most Americans cherished the frontier. Henry James had one of his characters in Washington Square say that the modest house he and his bride had taken would do for the moment, for they didn’t intend to remain there long. “At the end of three or four years, we’ll move. That’s the way to live in New York—to move every three or four years. Then you’ll always get the last thing. It’s because the city is growing so quick—you’ve got to keep up with it. It’s going straight up town—that’s where New York’s going.”

What was driving New York uptown was all the immigration downtown. Since Ireland’s famine of the 1840s, the largest stream of immigration had come from that hungry isle; the Irish joined an earlier and continuing effusion from the German-speaking lands of central Europe. At first a few of the immigrants sought shelter at the northern edge of the populated districts. Their habits dismayed those who had arrived earlier, causing the editor of the Evening Post to harrumph in distaste:

During the last few years, an immense population of poor Irish and Germans have settled on the vacant lots, between 37th and 50th streets. They have built their own cabins, and live there, the dogs, goats and pigs often all in the same room with the family. Their business is the poorest street or house labor. Picking rags, selling goats’ milk, gathering cinders from the ashes to sell to the other poor, cleaning the new houses, working on the docks; and among the Germans, making the wooden splinters for match manufacturers.

But as the moneyed classes fled the crush downtown, they evicted the squatters. These joined the larger number who had crowded into the older districts that the wealthy had left behind, either into their since-partitioned houses or into the newer, even more crowded tenements. Statistics told the tale of the difference between the upper and lower parts of the city. A housing reformer, Samuel Halliday, noted that the two miles of fashionable Fifth Avenue between the parade ground at Washington Square and the reservoir at Forty-second Street provided homes to some 400 families, while a single block of tenements farther south sheltered 700 families, or some 3,500 individuals. At a time when a square mile of London’s East End, the neighborhood so wrenchingly portrayed in the novels of Charles Dickens, contained 175,000 inhabitants, New York’s Fourth Ward had a population density of 290,000 per square mile. More crowded places on earth existed, but most Americans wouldn’t have considered them civilized. Many had similar doubts about the immigrant neighborhoods of lower New York.

The wealthy had another reason for moving uptown besides the breathing room that the new neighborhoods offered. They wanted to get wealthier—to cash in on the boom in real estate prices that the population explosion was driving. Halliday, after enumerating the density of the tenements, offered an explanation for their existence and a warning regarding the prospect of change. “The amount in-vested in tenant-houses in New York,” Halliday said, “together with the enormous percentage which they pay, has created an interest so great that the work of reforming the abuses connected with them will be no child’s play.” The influx of immigrants generated an insatiable demand for housing, and although the immigrant families couldn’t afford to pay much individually, collectively they could pay a great deal. Owners of tenements typically received returns of anywhere from 25 percent to 100 percent per year on their investments, far higher than the rates received by owners of housing rented to middle- and upper-class families. The arithmetic of the situation drove property values up, which in turn drove the more comfortable classes uptown, making many of them rich in the bargain.

The richest of all was John Jacob Astor. At his death in 1848, Astor was one of the wealthiest men in the world, with an estate conservatively valued at $20 million. The rental income alone from his properties topped $200,000 yearly. And yet he still regretted lost opportunities—in particular, the bargains in land he had missed. Asked what he would do differently, he replied, “Could I begin life again, knowing what I now know, and had the money to invest, I would buy every foot of land on the Island of Manhattan.”

Theodore Roosevelt’s people weren’t in the same league as Astor, but they played the same game. In the mid-nineteenth century, Cornelius Van Schaack Roosevelt, Theodore’s grandfather, ruled the clan from a brick mansion on Union Square. C.V.S., as the family called him, headed the firm of Roosevelt & Son, founded by his grandfather and father, originally merchandising hardware, more recently providing plate glass to New York’s busy builders. The company paid the family’s bills and provided employment for the adult sons. But the true source of the family’s wealth was real estate, which C.V.S. had cannily collected on the low side of the Panic of 1837. As Manhattan boomed during the middle decades of the century, so did the Roosevelt fortune. During one three-year stretch in the 1840s, Cornelius’s worth was estimated to have doubled, and it soon doubled again and then again. An 1868 listing in a nosy magazine placed him among Manhattan’s ten genuine millionaires. While he complained of the publicity, he didn’t dispute the veracity of the report.

As it lifted the Roosevelts and Astors and others similarly fortunate, the swelling tide of real estate values sifted the city socially, producing two distinct and only occasionally overlapping societies. Theodore Roosevelt was born into one; the other he would come to know professionally. The older wards were home to the poor, some honest, some not. The honest poor included the innumerable peddlers who plied their wares on the ferry landings and in front of the Merchants’ Exchange on Wall Street; of these the most visible, or at least the most audible, were the hot-corn girls, whose chant rose above the din of the streets:

Hot corn! Hot corn!

Here’s your lily-white corn!

All you that’s got money,

Poor me that’s got none—

Buy my lily-white corn

And let me go home.

The dishonest poor included the pickpockets, petty thieves, and criminals of somewhat grander ambitions who frequented City Hall Park, lower Broadway, and other less genteel parts of Manhattan. What truly disturbed respectable New Yorkers was not the existence of the criminal element—they had become inured to that—but the esteem in which its leaders were held by so many of the city’s inhabitants. One gangster, gunned down in 1855, was given a funeral that featured a full marching band and a procession of thousands of mourners, and attracted scores of thousands of onlookers. Horace Greeley’s Tribune, expressing the “disgust and contempt” that all public-spirited citizens must share, warned that the circumstances surrounding the slaying evinced a cultural shift of ominous proportions. A longtime New Yorker, Philip Hone, lamented that “the city is infested by gangs of hardened wretches, born in the haunts of infamy, brought up in taverns.” Such persons, said Hone, “patrol the streets making night hideous and insulting to all who are not strong enough to defend themselves.” An English visitor remarked, “The practice of carrying concealed arms, in the shape of stilettos for attack, and swordsticks for defense, if illegal, is perfectly common.… Terrible outrages and murderous assaults are matters of such nightly occurrence as to be thought hardly worthy of notice.”

Not surprisingly, the pervasiveness of crime brought calls for better policing of the city. In 1844 the state legislature ordered the mayor to reorganize and upgrade the city’s police force. Mayor James Harper attempted to do so by, among other means, mandating the wearing of uniforms. The policemen, who were accustomed to wearing ordinary clothes with a badge indicating their office, rebelled at the notion of what they derided as livery. Meanwhile, the city’s Board of Aldermen, refusing to be overruled by Albany, endorsed a separate reorganization plan, creating a separate police force. For a year the city had two rival police forces, which at one point fought a pitched battle on the steps of City Hall. Finally, in the interest of municipal peace, the aldermen acquiesced in the legislature’s plan, and after much persuasion the officers agreed to put on the blue uniforms that became their trademark.

Theodore Roosevelt would grow intimately acquainted with the problems of policing the city when he accepted the post of police commissioner; he would also become acquainted with the corruption that underlay the policing dispute and that generally characterized the government of the city. Corruption in New York took myriad forms. It allowed the city’s ten thousand prostitutes, for example, to practice their ostensibly illicit profession usually unmolested. The bolder practitioners, those whom diarist George Templeton Strong called the “noctivagous strumpetocracy,” brazenly paraded along Broadway. One client, more appreciative than Strong, described the high-toned streetwalkers: “Their complexions are pure white and red, and their dresses are of the most expensive material, and an ultra-fashionable make. Diamonds and bracelets flash from their bosoms and bare arms, and heavily-wrought India shawls, of that gorgeous scarlet whose beaming hue intoxicates the eye, hang carelessly from their superb shoulders, almost trailing on the walk.” Every now and then the police would raid a brothel, to remind its owner why they were being paid off. After one such raid, the Herald intoned, “Clerks of respectable mercantile houses were found in this pious place in the embraces of the most depraved and abandoned denizens of the notorious spot. They were compelled to give their names and the names of their employers. They were then suffered to go home, covered with shame and mortification.”

Corruption in the city had many other faces. The most familiar watched over the development of public works. Providing the necessities of life to a population that was rapidly approaching one million was a heroic undertaking; one landmark victory came in 1842 with the opening of the Croton water system. Connecting a storage reservoir on the Croton River in upper Westchester County to distribution reservoirs on Forty-second and Eighty-sixth Streets by means of a conduit eight feet in diameter and forty-five miles long, the Croton system brought a flood of fresh water into the city and allowed the city’s breathtaking growth to continue unabated. “Nothing is talked of or thought of in New York but Croton water…” Philip Hone wrote. “Political spouting has given way to waterspouts, and the free current of water has diverted the attention of the people from the vexed question of the confused state of the national currency.… Water! water! is the universal note which is sounded through every part of the city, and infuses joy and exultation into the masses.”

Public works necessitated public funding, in the expenditure of which numerous temptations to diversion arose. New York officials were perhaps no more susceptible to temptation than others of their era, but they were demonstrably no less. And none was more human in this regard than William Marcy Tweed, the boss of New York’s Democratic Party. Boss Tweed had gifts well suited to an age that lionized schemers and connivers, but where the legal lions did their scheming and conniving in the private sector, Tweed and his Tammany Hall colleagues were more publicly minded. During the 1850s and 1860s, they brought to the government of New York City the same sorts of shenanigans that were cornering markets, watering stocks, and fleecing investors in the corporate world. Their most breathtaking project, the construction of the County Courthouse at City Hall Park, netted the Tweed ring millions of dollars before being revealed in all its grafting glory, and it included such ornaments to civic pride as enough carpet to cover a highway reaching halfway to Albany—paid for but, needless to say, never delivered. Heaping insult atop injury, a special committee appointed to probe the case charged the city more than $18,000 for twelve days’ deliberation.


Theodore Roosevelt would get to grapple with both the gangsters of the street and the bilkers of the boardroom. But before he did, he had to survive a sheltered youth in the world of upper-class New York. It wasn’t easy. By his tenth birthday he had been nearly pampered to death—repeatedly. To be fair to his parents, it wasn’t precisely the pampering that carried him to death’s doorstep; it was the asthma. But the pampering didn’t help, and quite possibly it hurt.

Roosevelt’s was a sick family—not dysfunctional but ill. His father died at the age of forty-six from cancer. His mother, never robust, succumbed to typhoid fever at forty-eight. His elder sister, Anna, nicknamed Bamie (short for bambina and pronounced “bammie”), suffered from a congenital bone disease that warped her spine and left her partly disabled. His younger sister, Corinne, called Conie, had asthma. His younger brother, Elliott, suffered from emotional illness and perhaps epilepsy, and eventually from chemical dependencies that led to his early death.

But it was Theodore—or Teedie, distinguishing him from his father, also Theodore (often The—pronounced Thee, and sometimes so spelled)—who was the frailest. Almost from his birth, on the evening of October 27, 1858, at the family house on East Twentieth Street, the boy suffered from one ailment after another. As an infant he was chronically uncomfortable; when he got old enough to say what was hurting, he described headaches, fevers, stomach pains, intestinal groanings, and as many other maladies as he had names for.

Most serious was his asthma. First appearing not long after he learned to talk, it recurrently seized the child by the bronchi and nearly suffocated him. The illness was only vaguely understood at the time, although an inherited predisposition was suspected, and a connection was recognized between the onset of attacks and various airborne irritants: coal dust (a pervasive problem in an age when coal heated houses, fired factories, and drove trains), powdered horse dung (another problem endemic to city life in the pre-automobile era), pollen, molds, and the like. In addition, asthma researchers noticed an emotional or psychological element in the disease, although what that element was in any particular case remained elusive.

In Teedie’s case the attacks came at intervals lasting from several hours to several days or sometimes even weeks. They were terrifying; try as he might to breathe, he couldn’t get enough air. He gasped and wheezed and choked, not knowing whether each frantic gasp might be his last. And when the attacks finally eased, he lay sweat-soaked, trembling, and exhausted, torn between relief at having survived and dread at the thought of the next such encounter.

The attacks were equally terrifying for his parents, if in a slightly different way. Helpless to prevent the attacks, neither could they alleviate them. No medications existed to open the swollen air passages. Caffeine sometimes seemed to work; one recommendation was to ply the patient with the blackest, strongest coffee brewable. But equally often the bitter stuff merely made the patient vomit. Nicotine, another stimulant, was also recommended, producing the paradoxical sight of a young child, already strangling on his own breath, trying to smoke a fat cigar. On the other hand, sedatives such as alcohol had their partisans; under this regimen, asthmatic children knocked back shots of whiskey. That all-purpose palliative of the Victorian era—opium—soothed some sufferers. Assorted other remedies, often equally contradictory, testified to the general state of confusion surrounding the condition.

Teedie’s parents tried everything they could think of. Nothing worked anywhere near reliably. When the fits came, the only thing they could do was hold him, walk him around, and try to comfort him. Given the slight stature and uncertain constitution of his mother, this chore fell to his father, the more as Teedie grew older. As a result, the boy came to associate the attacks—unconsciously, to be sure—with an opportunity to receive his father’s undivided attention. Teedie’s father was hardly a cold or remote figure to his children, but he was a busy man who spent the great majority of his waking hours away from home. Moreover, Teedie had three siblings who also competed for their father’s attention. Quite possibly it didn’t escape Teedie’s notice that their father particularly doted on Bamie, who had the bone disease. In any event, it definitely didn’t escape his notice that during his attacks he became the center of his father’s world. Bamie could wait; Elliott and Conie could wait; his mother could wait; his father’s outside activities could wait. His father would pick him up in strong, reassuring arms. Fresh air sometimes seemed to afford relief: often at night his father would bundle him in blankets and take him for a fast ride through the darkened streets of Manhattan—a thrill the young child could appreciate as the siege of his pulmonary system gradually lifted.

All of which is not to imply that Teedie’s asthma was anything but a real disease or was merely in his head. It most definitely was in his lungs. Yet many diseases have psychological components, asthma among them. And as distressing as the physical manifestations of the attacks were, some of the emotional consequences could be distinctly rewarding. It isn’t surprising that they occurred as often as they did.


Teedie would have idolized his father even without the asthma. The elder Theodore Roosevelt was an easy man for his children to idolize. He was a large, powerful figure with a broad forehead, strong brow and nose, full bristling beard, and sparkling blue eyes that revealed beneath the distinguished demeanor a soul that had never lost the joyfulness of youth. Theodore was the youngest of grandfather C.V.S.’s five surviving offspring—all boys (a sixth boy died as a baby). As children, the group—Silas Weir, James Alfred, Cornelius Jr., Robert Barnhill, and Theodore—made quite an impression on polite New York society. The neighbors spoke of “that lovely Mrs. Roosevelt” and her “five horrid boys.” James took most after their father in temperament and interests, and it was to James that Cornelius handed direction of the family’s business affairs, including management of the Broadway Improvement Association, the corporate entity that controlled the family’s property holdings. Robert, the maverick of the bunch, went into politics (discreetly allowing his given middle name to be corrupted to Barnwell, which he considered less likely to afford an opening to slander-minded opponents who might liken a Barnhill to a manure pile). Setting something of a precedent for his nephew, Robert campaigned to recapture New York politics from the machinations of the Tweed ring. He also established another family precedent by making the conservation of natural resources a priority. His efforts at saving the shad run on the Hudson River brought him international attention; when the British minister in Washington requested information on the subject, Secretary of State Hamilton Fish, who presumably chose words on this subject with care, directed him to Robert Roosevelt as “the Father of all the fishes.”

Theodore joined brother James in the family business. But he never warmed to it the way James did. He had neither passion nor flair for commerce and found the whole thing rather a bore. His blood might have been stirred by the thought of helping to build the great metropolis, of providing, literally, windows on the world to the thousands of the present and the millions of the future. But it didn’t. Neither did he conceive of money-making as the test of a man’s mettle in the dawning age of industry.

Yet if Theodore fell short in the art of making money, he knew well enough how to spend it. He had an eye for the finer things in life. He kept himself impeccably attired, partly to befit his station in society but also, apparently, to offset his childhood experience as the last of five boys and the recipient of the others’ hand-me-downs. Once, overhearing his mother say, for what seemed the thousandth time, “These were Robert’s, but will be a good change for Theodore,” he objected vociferously that he was “tired of changes.” As an adult he bought only the best clothing. He was an accomplished horseman and kept the most handsome mounts; when he took his family out for a drive, his coach and team—not to mention his fast driving—made onlookers turn and stare. The house on Twentieth Street that all his children were born in was a wedding gift from his father; while it wasn’t especially imposing or luxurious, Theodore never stinted on its operation and maintenance.

Theodore’s generous ways extended well beyond his family circle. He was a pioneer of a new class in America: committed and essentially full-time philanthropists. Charity had existed from time out of mind, of course, but in America during the nineteenth century it became organized as never before—at a time, not coincidentally, when most other areas of life were becoming similarly organized, and when poverty was becoming increasingly entrenched and visible. Theodore Roosevelt Sr. once remarked that he possessed a “troublesome conscience”; that conscience inspired him to activities that he found far more engrossing, and rewarding, than peddling plate glass. He helped found the Children’s Aid Society and the State Charities Aid Association. He spearheaded a drive to establish the Newsboys’ Lodging House, a shelter for Ragged Dicks who had pluck but not so much luck; most Sunday evenings were spent with the newsboys, inquiring after their activities and dreams, and sharing some of his own.

A special project was the New York Orthopedic Hospital. Bamie’s affliction attuned her father to the sufferings of similarly stricken children, and it acquainted him with New York’s leading doctors in the field. He initially tried to talk his friends and business associates into backing a state-of-the-art orthopedic hospital, but they claimed other causes as reason to decline. So one spring afternoon he held a small party at the family house, to all appearances a strictly social gathering. When the guests, representing New York’s most prominent and affluent families, arrived, he had several poor children in need of orthopedic treatment brought in and introduced to the guests. The effect was exactly as he had hoped. Mrs. John Jacob Astor turned to him and declared, “Theodore, you are right; these children must be restored and made into active citizens again, and I for one will help you in your work.” Mrs. Astor’s pledge precipitated others, and by afternoon’s end enough money had been raised to get the orthopedic hospital up and running.

This event and others like it won Theodore a reputation as an irresistible solicitor for worthy causes. Friends and business acquaintances came to recognize a characteristic gleam in his eye; most would surrender without a fight, asking merely, “How much this time, Theodore?”

Theodore put his fund-raising skills to work for the Union during the Civil War. Not long after the fighting began, he journeyed to Washington to lobby for legislation to guarantee that the families of the men under arms would not suffer unnecessarily from their absence. He pressed for a bill that would facilitate the voluntary allotment of part of each soldier’s pay to his family. The measure struck most of the legislators as patriotic and reasonable, and it passed without difficulty. After it did, Theodore accepted an unpaid appointment as one of New York’s allotment commissioners. In this capacity he traveled from camp to camp, encouraging the troops to earmark a set portion each month for their loved ones at home. He proved as adept at opening the soldiers’ pay envelopes as he was at prying money loose from the likes of the widow Astor. “The men looked as hard as I have often seen such men look in our Mission neighborhood,” he wrote home on New Year’s Day, 1862, “but after a little talking and explaining my object and reminding them of those they had left behind them, one after another put down his name, and from this company alone, they allotted, while I was there, $600.00.… One man, after putting down five dollars a month, said suddenly, ‘My old woman has always been good to me, and if you please, change it to ten.’ In a moment, half a dozen others followed his example and doubled their allotments.”



  • "A rip-roaring life of Theodore Roosevelt, in my view the most lovable, fascinating and creative of American presidents. Every red-blooded American should read this entertaining book.... Mr. Brands calls T.R. the last romantic, and it is true."—Paul Johnson, Wall Street Journal
  • "Roosevelt's life in Mr. Brands' able hands is a demonstration of the remarkable power of the human will. Roosevelt literally created the character he lived out, and then lived within it until he finally became his creation."—Washington Post
  • "Brands makes the case that Roosevelt believed in heroes and measured himself against giants of history and literature.... He puts them in vivid context with often wry narration and an impressive depth of historical research."—USA Today
  • "Brands outlines with suitable vigor the most important aspects of T.R.'s presidential years.... It seems likely that T.R. will stand for some time as the standard one-volume life."—Chicago Sun Times
  • "Brands shows how this hero of the charge up San Juan Hill, more than anyone else, led the United States onto the world stage."—Los Angeles Times
  • "Brands' narrative is lucid, fast-moving and unblended by hero-worship. In a single volume he has packed Roosevelt's 60 years of ambition, adventure, expediency, achievement, and, finally, frustration at having peaked too soon."—Publishers Weekly

On Sale
Aug 13, 2019
Hachette Audio

H. W. Brands

About the Author

H. W. Brands holds the Jack S. Blanton Sr. chair in history at the University of Texas at Austin. A New York Times-bestselling author, he was a finalist for the Pulitzer Prize in biography for The First American and Traitor to His Class. He lives in Austin, Texas.

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