How Teddy Roosevelt Diffused a Scandal by Destroying His Brother’s Marriage

Theodore Roosevelt styled himself an incorruptible politician untainted by scandal. But in his path to the White House lay a troubling obstacle: his scapegrace brother, Elliott.

Photo Illustration by Kelly Caminero/The Daily Beast

The untold story of the illegitimate Roosevelt son and the family’s scheme to keep him hidden reveals the secret pain that was carried by First Lady Eleanor Roosevelt all her life, as well as the fact that the successful management of political sex scandals is hardly a 21st century accomplishment. In previous accounts, Theodore Roosevelt’s actions in 1891—1894, when he did his best to commit his brother to an asylum, even if that meant splitting up Elliott’s family, have been presented as noble and inevitable. I take a different view.

William J. Mann

Theodore Roosevelt wanted to be president more than anything. As a young man serving on the Civil Service Commission in 1891, he would often walk past the White House on his way home and his “heart would beat a little faster,” he admitted. He was in a hurry to get ahead. Still smarting over losing the New York mayoral race two years earlier, the thirty-two-year-old Republican loyalist didn’t want to be some gray-bearded codger when he finally grabbed the brass ring. He didn’t want to be President Benjamin Harrison, “the little gray man in the White House,” as Theodore called him. He wanted to make his move now.

But he had a problem. In a name: his brother Elliott.

Alone at night, after his wife Edith and his three children had gone to bed, Theodore sat at his desk and wrote letters to his sister Anna, called Bye, ruminating over their reckless brother. In January, Theodore had received a letter from the New York law offices of William Howe and Abraham Hummel, lawyers best known for defending prostitutes and saloonkeepers. They informed him that Elliott had gotten one of the chambermaids in his house pregnant, and the woman was in dire need of money. Theodore had no idea if the woman was telling the truth or merely a con artist, but it was indicative of the kind of life Elliott led that such a claim could even be made. Theodore’s brother drank too much and showed no respect for proprieties. For the past few years he’d been embarrassing the family at social gatherings. At one soiree thrown by Bye, he’d been rude to her guests, finding them insufferably snooty. “It is a perfect nightmare about Elliott,” Theodore told his sister after getting a report of the evening. “I am distressed beyond measure.”

At the moment, Elliott was in Europe, living beyond his means with his extravagant wife, Anna. Stories of their high-flying lifestyle were frequent. As any man with his eye on the presidency would be, Theodore was keenly aware of decorum and discretion, and he knew party bosses would be reluctant about backing a candidate with a black sheep such as Elliott in his family. Only seven years earlier, after all, cries of “Ma, Ma, where’s my pa?” had threatened to derail Grover Cleveland’s campaign for president. Taunted about stories of an illegitimate son, Cleveland barely won an election he was supposed to have taken handily, eking out a win in the popular vote by just one quarter of one percent. (He did far better in the electoral vote tally.) Until the end, a Cleveland win remained in doubt, with preachers blasting him from their pulpits and the Republican press publishing frequent heartrending affidavits from the mother of the little boy.

Such dishonor could not attach itself to Theodore. After years of government corruption, he was positioning himself as a new kind of politician: moral, principled, incorruptible. His whole public persona was predicated on his integrity and character. His intolerance of backroom deals was well known: Theodore refused to countenance patronage or misconduct of any kind. That was why Elliott’s shenanigans were potentially so dangerous.

The rivalry between the two brothers had begun when they were very young, when Theodore, the elder brother, had suffered from asthma, depending on Elliott to get up the stairs. But after the asthma faded and Theodore started lifting weights, he’d found himself beating Elliott in athletic contests, much to their father’s surprise and admiration. Elliott discovered other ways to attract paternal notice, even if it wasn’t always laudatory. Better looking than his brother, Elliott was a playboy, carrying on a string of romances from his young teens. “All the girls,” Theodore would recall wistfully, “used to be so flattered by any attentions from him.” Theodore, on the other hand, possessed a puritanical streak, engaging in few romantic adventures until he met the woman who’d become his wife. Elliott’s fondness for women had continued. How many other chambermaids, his brother feared, might come forward? Such sexual impropriety offended Theodore to his core.

There was only one answer. If indeed a chambermaid was carrying his child, Elliott had to be separated from his wife and children. Appearances were everything. “If some frightful scandal arises,” Theodore wrote to Bye, “it should be widely known that we regarded him as irresponsible, that Anna had left him with the children, and that we stood by Anna.” Although Elliott had stopped drinking—a fact insisted on by his wife and corroborated by Bye when she visited them in Europe—Theodore declared his brother needed to be institutionalized. Elliott’s welfare, he bluntly told Bye, was “only secondary.” The safety and reputation of Anna and the children should now be their only concern, he wrote—except for Theodore’s career, of course, though that hardly needed to be said.


Getting Elliott into an asylum was never going to be easy. But Theodore had another battlefront in his effort to suppress the scandal: the pregnant chambermaid. Katie Mann had come to America from Germany at the age of twenty-three, an idealistic young woman who wanted, her descendants said, to find “someone to marry, have babies, and live in a house with a garden all her own.”

Soon after her arrival, Katie took a job as a servant to the Elliott Roosevelts at their house on 29 East Thirty-Eighth Street. At first, she spoke little English; she picked up words and phrases by overhearing governesses teaching Elliott’s daughter, Eleanor, who was fond of Katie. Elliott was fond of the chambermaid too. Occasionally, at night, he would come by Katie’s room to talk. Very quickly, Katie fell in love with the charming, handsome man; she came to believe Elliott loved her as well. At one point, her family would reveal, they even pledged their troth to each other. “Katie Mann was the victim of a mock marriage,” her granddaughter would say years later, “an immigrant girl who was confused and [who] believed the drunken Elliott Roosevelt when he ‘married’ her.” Elliott called Katie his “spiritual wife.”

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Then, apparently, his actual wife discovered their rendezvous, because all at once the family packed up, closed the house, and sailed off for Europe. Not only was Katie out of a job and bereft of her lover, but a short time later, she discovered she was pregnant. From Bad Reichenhall, Germany, she received a photo in the mail of little Eleanor. She tried replying to the letter but Elliott was constantly moving. No word reached him of her condition. Living in a small flat in Brooklyn with her mother, Katie took in laundry, barely making the rent. She felt desperate.

When the baby came, in May 1891, Theodore sent a police detective out to get a look. Named Elliott after his father, the boy’s “Rooseveltian features” convinced the detective that Katie was telling the truth.

Theodore needed to see for himself. On July 13, he made his way to the Brooklyn tenement where Katie lived. The big, barrel-chested man seemed to take up all the space in the little room. For the first time, the commissioner and the chambermaid stood face-to-face. From behind his spectacles, Theodore’s beady eyes glared at Katie. So this was the girl who might stand between him and the White House. Katie did not flinch in his gaze. She presented him with his nephew. Evidently Theodore’s reaction was much the same as the detective’s, as he made no further objection to paying Katie some money.

She’d have to do something for him in return, however, Theodore told her. Katie needed to give her word that she’d make no further claims on the family and never tell anyone who the boy’s father was.

Katie accepted Theodore’s terms. She had no desire for a scandal. All she cared about was her son’s future. She dropped her own lawyers, Howe and Hummel—known for their aggressive and showy courtroom style—and accepted representation from Frank Weeks, who secretly worked closely with Theodore. As payment for her silence and exile, Katie was promised four thousand dollars. The money, she was told, would be paid to her by Weeks.

Meanwhile, in Paris, Elliott was drinking again, furious at his brother’s meddling in his life. He’d agreed to spend a few months in a sanitarium, but no more. That wasn’t enough to satisfy Theodore, who knew if the scandal become public, Elliott needed to be already securely locked away. In July 1891, Elliott was forcibly removed from his home in Paris—he described it as a “kidnapping”—and placed under a doctor’s care, allowing Bye to whisk Anna and the children back to America. Elliott’s seven-year-old daughter, Eleanor, was traumatized.

The lanky and awkward little girl had never received much tenderness from her mother, who seemed disappointed that she wasn’t as pretty as other girls in her family. Eleanor had a weak chin and an overbite, but her eyes were cerulean blue and full of soul and they left her father enchanted. Elliott discerned possibilities in Eleanor that everyone else seemed to miss. He looked upon her “shortcomings with a much more forgiving eye,” Eleanor would remember. He gave her “warmth and devotion,” she said, and “some badly needed reassurance.”

So when she and her mother, brothers, and Auntie Bye sailed back to New York on August 1, 1891, without her father, Eleanor was bereft. In many ways, she would remain that frightened little girl trembling on the bow of the ship, yearning for her father, for the rest of her life.

Theodore had succeeded, for appearance’s sake, in breaking up the family, but ultimately he failed in his plans to institutionalize his brother. When Elliott was brought back to America, he was declared sane and competent by two different courts. The damage was done, however. The nation’s newspapers had headlined elliott roosevelt insane during Theodore’s attempt at conservatorship. A scandalized public devoured salacious details about the glamorous young playboy who’d once been a regular name on the society pages. “Excessive indulgence in drink… Entertained lavishly, went out in society too frequently… ” Given his public humiliation, Elliott had no choice but to accept his brother’s decree that he not to see his wife or children. Only a handful of times did Eleanor see her father after that. Depressed and miserable, Elliott drank himself to death in 1894.

To Theodore’s mind, he’d made the best of a very bad situation. He might not have been able to avoid the scandal, but he had contained it: there was no mention of Katie Mann and the child. And despite the difficulties his actions had caused for Elliott’s wife and children, the situation was far better, Theodore believed, than if they’d been permitted to stay with him and remain a family. “Any poverty would be better for the children,” he wrote to Bye, “than to be brought up in that degradation of association with Elliott.”

For the rest of her life, Eleanor would passionately disagree. “I needed my father’s warmth and devotion more perhaps than the average child, who would have taken love for granted and not worried about it,” she would write. Her childhood would be delineated by the theft of her father: a time before and a time after. Nothing was ever the same for her. Two years earlier, on her fourth birthday, Eleanor’s parents had thrown her a party, and her father had showered her with presents and kisses. She was the apple of his eye, his darling, the happiest of little girls. After the party, a delighted Elliott wrote to Bye that his daughter had gone to bed declaring she “loved everybody and everybody loved her.” Never again would Eleanor feel that way.

Another child left was bereft as well: Elliott’s namesake son with Katie Mann. Thirty miles and a world away from his wealthy uncle, cousins and siblings, two-year-old Elliott Roosevelt Mann lived in a rundown Brooklyn tenement. Every day he and his mother worried they’d be tossed out onto the street.

Katie Mann had hoped by now she and her son would be far away from this place, having used the money from the Roosevelts to find themselves a home. All she wanted was a couple of rooms, with enough land for a small garden. Yet Katie hadn’t seen a dime. Frank Weeks, the lawyer so trusted by Theodore to handle his brother’s affairs, had absconded with the money. Weeks’s crime was surely known to the Roosevelt clan: as it turned out, he’d been embezzling clients all over New York, from various Astors to an American-born countess. The newspapers were filled with accounts of Weeks’s arrest and his sentence to ten years of hard labor at Sing Sing. Surely Theodore and his sister Bye must have wondered whether the money that had been earmarked for Katie and for their nephew had ever been received. If either of them ever made inquiries, though, neither left any record of doing so. And Katie’s family insisted they had not. Apparently, it was best not to ask questions when they did not want to know the answers.

Katie had appealed one last time for help, visiting a Roosevelt brother-in-law soon after Elliott’s death. “Katie Mann came in to Douglas’s office with the child,” Theodore wrote to Bye, “which she swears was [Elliott’s]. I have no idea whether it was or not… but her story may have been partly true. We cannot know.” Keeping alive the possibility that Katie was a con artist made it easier to deny her financial support. “She was a bad woman,” Theodore told Bye, without any justification, without knowing a thing about Katie or her character, judging her from a distance, through a cloud of presumption and his own fears.

Empty-handed, Katie returned to Brooklyn to raise her child as best she could. Sometimes she lamented the fact that she’d left Howe and Hummel, that she’d allowed herself to be swayed by Frank Weeks, who, she came to realize, had been in the pocket of the Roosevelts. Yet Katie didn’t spend much time brooding over regrets. She couldn’t, her family said. She had a little boy to raise.

True to her word, Katie kept the secret of her son’s paternity and never contacted the Roosevelt family again, not even after Theodore became president in 1901. The same, however, would not be true of her son.

Excerpted from The Wars of the Roosevelts. Copyright © 2016 by William J. Mann. Reprinted with permission of Harper, an imprint of HarperCollins Publishers.

William J. Mann is the author of Tinseltown: Murder, Morphine, Madness at the Dawn of Hollywood, winner of the 2015 Edgar Award for Best Fact Crime, as well as Kate: The Woman Who Was Hepburn, How to be a Movie Star: Elizabeth Taylor in Hollywood, and several other best-selling titles. His biography Wisecracker: The Life and Times of William Haines won the 1999 Lambda Literary Award. He divides his time between Connecticut and Cape Cod.