Island of Vice

by Richard Zacks

  “Teedie” and “Ellie,” as they were called, shared the rarefied life of the Roosevelt clan on 20th Street. They had stood shoulder to shoulder at the second-story window and watched the Lincoln funeral procession in 1865; they shared private tutors (never attending public or private school) and performed scenes from Shakespeare under the direction of the family doctor; they endured dour family Sundays and took Grand Tours together to Europe and Egypt. They played in the gardens of Fontainebleau and floated down the Nile on a dahabeah for two months with thirteen servants. On that trip, twelve-year-old Elliott hadn’t discovered hunting yet, but Theodore, with new spectacles, blasted birds with his new 12-gauge double-barreled French shotgun; then he gutted and stuffed them on the deck to preserve them as specimens. His blood-drenched clothes made him a family outcast, inspiring a limerick by Elliott.

  There once was an old fellow named Teedie

  Whose clothes at best looked so seedy

  That his friends in dismay

  Hollered out, “Oh, I say!”

  At this dirty old fellow named Teedie.

  As siblings often do, each carved out his niche. Elliott became the ballroom dancer, athlete, the charmer of women; Theodore was the bookish one who kept a diary and tried extremely hard at everything. TR would later reminisce about “dancing class” where Elliott far outshone him. “He was distinctly the polished man of the world from the outside, and all the girls from Helen White and Fanny Dana and May Wigham used to be so flattered by any attention from him.”

  They summered together, first in New Jersey, then at Oyster Bay; they rode horses bought for them by their father. Elliott excelled at sailing, while Theodore became the relentlessly determined rower.

  Both suffered severe childhood illnesses that upended family outings, provoking immense worry by their parents and perhaps jangling relations between them. Theodore from age three endured frightening deep-gasping bouts of asthma, which he later combated with extraordinary gym workouts. Elliott seemed the golden child until suddenly at puberty he started having seizure-like attacks, diagnosed as “nerves/hysteria,” with fainting, headaches, and night terrors.

  Their philanthropist father, Theodore Roosevelt Sr., tried hard to prevent them from turning into the frivolous boys of Fifth Avenue. Father, known as “Great Heart,” preached and also practiced an active Christianity that demanded good works. He founded the Newsboys’ Lodging House to shelter hundreds of orphans sleeping in alleyways and gutters; during the Civil War he had helped create the Allotment Commission, which encouraged soldiers to send their pay home to their families instead of squandering it on whores and saloons.

  Theodore seemed challenged to live up to his father’s lofty aspirations; Elliott often seemed chafed by them.

  As part of a cure for Elliott’s fits, the family sent him at age sixteen to a military outpost, Ft. McKavett in the wilds of Central Texas. Elliott wrote about bunking with a genuine cowboy in a tumbledown hut, sharing a blanket with the stranger, and deciding to use a dog as a pillow “partly for warmth and partly to drown the smell of my bedfellow.” Theodore was very jealous.

  Together, they weathered the sudden shock of their father’s death in 1878. As they grew older, the lives of the two brothers intertwined less, with Theodore off at Harvard and Elliott still too troubled to study, but Elliott took his brother—just before Theodore’s marriage to his first wife, Alice Lee—on a kind of extended bachelor party, a hunting trip out west as far as the Red River in Minnesota. Though they had no Indian adventures, the brothers shot more than 400 birds—geese, snipe, plovers, ducks—and nearly drowned, after upending a rowboat in Iowa. “I enjoy being with the old boy so much,” Theodore wrote, and Elliott echoed the sentiment: “All the happier we are solely dependent on each other for companionship.” Elliott appeared to be outgrowing the anxiety attacks, or perhaps he had discovered how to blot them out with cocktails.

  Theodore described his twenty-year-old brother reaching Chicago during their trip: “As soon as we got here, he took some ale to get the dust out of his throat; then a milk punch because he was thirsty; a mint julep because it was hot; a brandy smash ‘to keep the cold out of his stomach’; and then sherry and bitters to give him an appetite.”

  TR’s flippant tone makes it unlikely he recognized his brother’s incipient alcoholism, but clearly Elliott was downing more than a few. He obviously wasn’t sloppy about it yet because Theodore asked Elliott to serve as best man at his Boston Brahmin wedding to Alice Lee on TR’s twenty-second birthday. “She is so pure and holy, it seems almost profanation to touch her,” Roosevelt wrote in his diary, but added that nonetheless he couldn’t stop hugging her.

  As a newly married man, Theodore embarked on his plans to be a writer and enter politics in New York. Meanwhile, best man Elliott sailed for India. Cavalier and footloose, Elliott hunted tigers south of Hyderabad, traveling by elephant, by horse, by servant-hoisted palanquin. Camp meals rivaled the catered baskets of Delmonico’s as they dined on an assortment of curries, chicken, veal, salmon, duck, and tongue, washed down by a cool pitcher of beer.

  Elliott proudly recorded that he had shot a nine-foot-long Bengal tiger as it was making its final lunge toward him. He wished his “brave, old Heart of Oak brother” could have been there. “It is the life, old man. Our kind. The glorious freedom, the greatest excitement.” A London taxidermist deftly fashioned the tiger’s skin into a rug that would cover the floor of the Roosevelt family parlor for years.

  Elliott circled the globe, then returned to join the polo-playing, hard-carousing fellows of Long Island. On December 1, 1883, he married the regally beautiful debutante Anna Hall in “one of the most brilliant weddings of the season,” attended by Astors and Vanderbilts. A crescent of diamonds held her veil in place. Anna, who almost a year later gave birth to daughter Eleanor and then five years after that to son Elliott, would remain beautiful enough to win accolades at society dinners. Elliott belonged to several prestigious Manhattan clubs and was working as a stockbroker.

  Theirs seemed the perfect marriage, only it wasn’t.

  Elliott “drank like a fish and ran after the ladies,” later commented a Roosevelt family member, “I mean ladies not in his own rank, which was much worse.”

  He also began having bizarre athletic accidents, probably from his recklessness and drinking. He fell attempting a double somersault during an “amateur circus exhibition” in Pelham, New York, in 1888 and cracked his ankle; a doctor’s misdiagnosis of the injury as a sprain led to the ankle having to be rebroken to be set, all of which dragged out his recovery and probably accelerated his use of opium-based painkillers.

  In late June of 1890, the twenty-nine-year-old German-born live-in house servant Catharina “Katy” Mann informed Elliott that she was pregnant with his child. Weeks later, Elliott and his wife Anna, their two children, and several servants (not including Katy) headed off to the elegant spas and hotels of Europe. The family’s plan was for him to dry out. Count Bismarck entertained them in Berlin, as did Count Sierstorff, who intervened when Buffalo Bill, then touring there, offered Elliott a shot glass of whiskey.

  Anna became pregnant again; Elliott remained sober for two months, feeding the pigeons in Piazza San Marco in Venice, sailing every morning with his two children near Naples. Then he cracked. Wife Anna wrote and asked if the most efficient member of the Roosevelt clan, unmarried older sister Bamie, would come over to Vienna to tend to her till she gave birth and try to convince her brother to dry out in a sanitarium.

  Elliott had other ideas; he soon headed to Paris, inviting the family to tag along. Once there he would disappear for days, one time hunting boar with the Duc de Grammont. “The horns played a little, then we galloped in a single file up and down miles of beaten forest road,” he wrote to one of his polo chums on Long Island. He complained that the only excitement possible in such a stage-managed hunt could occur if someone fell asleep and tumbled off his horse.

  Back in New York, Katy Mann—pregn
ant, abandoned, and living at home in Brooklyn with her mother—approached the Roosevelt family, told her story, and demanded money. Older brother Theodore, then in D.C. serving on the Civil Service Commission, and brother-in-law Douglas Robinson (married to his younger sister, Corinne), in New York, handled the negotiations. TR at first did not believe the servant, until she said she had a locket and witnesses who had heard Elliott in her room. She claimed it was common knowledge that the other servants “chaffed” her about the master’s attentions.

  “It is like a brooding nightmare,” wrote TR to his sister Bamie in Europe, painting the adultery in stark Victorian terms. “If it was mere death one could stand it; it is the shame that is so fearful.”

  TR wanted Bamie to convince Elliott to allow himself to be locked up in an asylum for a long cure. In any case, he expected his brother’s living arrangements to change drastically. “Personally, I regard it as little short of criminal for Anna to continue to live with him and bear his children. She ought not to have any more children and those she has ought to be brought up away from him.”

  He advised his sister that as soon as Anna gave birth and recovered, she should bring the family home to the United States and leave Elliott in a foreign asylum, preferably a long-term, or possibly “permanent,” arrangement. He added that if she couldn’t persuade Elliott to go to one in Europe, he would have him locked up as soon as Elliott returned to America. “His curious callousness and selfishness, his disregard of your words and my letters and his light heartedness under them, make one feel hopeless about him.” TR feared that “the Katy Mann affair is but the beginning.”

  Theodore regarded Elliott’s drunken infidelity in black-and-white terms: Elliott was either “insane,” that is, not responsible and deserving of treatment or … his brother was sane, responsible, and a “selfish, brutal and vicious criminal.”

  Katy Mann gave birth and demanded the large sum of $10,000. TR and his brother-in-law Douglas sent an investigator, carrying a picture of Elliott, to Brooklyn to examine the baby. He confirmed that it was probably a Roo-sevelt. “It is his business to be an expert in likenesses,” wrote TR. They mulled a counteroffer of $3,000 or $4,000 in exchange for a quit-claim.

  The Dutch Roosevelts, one of New York’s oldest families, had never been touched by scandal. Most family members preferred to keep this quiet as long as possible, certainly not volunteer it to the press. Nonetheless, Theodore and Bamie—convinced they needed to protect Anna and the family fortune—applied to the New York courts for a writ of insanity against Elliott. With that filing, the scandal finally broke, with front-page headlines: DEMENTED BY EXCESS, WRECKED BY LIQUOR AND FOLLY, and PROCEEDINGS TO SAVE THE ESTATE. In his affidavit Roosevelt stated his brother had threatened suicide several times and had lost his power of self-control. Bamie stated that Elliott had been drinking to excess for the past three years but had turned irrational and violent in the past year.

  However, Roosevelt’s younger sister, Corinne, the flightiest and most emotional of the four siblings, refused to join in the court proceeding. Years earlier, she had written: “Dear Elliott has been such a loving tender brother to me … How different people are … there is Teddy, for instance, he is devoted to me too but if I were to do something that he thought very weak or wrong, he would never forgive me, whereas Elliott no matter how much he might despise the sin, would forgive the sinner.”

  The judge appointed a three-person commission of lunacy to evaluate the thirty-one-year-old bon vivant, currently in Paris. If he was ruled a lunatic, the court would appoint an executor to oversee his immense $175,000 estate. Throughout his letters, TR sounded a recurrent theme of wanting to preserve the estate for Elliott’s wife and children, as Elliott was apparently blowing through about $1,500 a month skittering around Europe, which would exceed his annual investment income.

  Each of the four Roosevelt siblings had received approximately $125,000 from their father and $62,500 from their mother.

  Following his boyhood cowboy dream, TR had invested $85,000 to buy two ranches and herds of cattle in North Dakota; in one letter describing a sudden ice storm, he stated that he hoped to lose “less than half” the money. He had bought property and built a home for $45,000 in Oyster Bay. Thanks to his financial decisions, TR had seen his annual income drop from about $14,000 a year in the mid-1880s to $7,500 in 1894 prior to taking the police commissioner job. In one recent year, wife Edith’s account books revealed an annual shortfall of more than $1,000. Roosevelt was eventually forced to sell off land in Oyster Bay. He even feared losing Sagamore Hill. He was famously impractical about money. Decades later, his daughter Alice noted that every morning her mother pinned a $20 bill in his pocket, and her father had no idea how he spent it.

  On the other hand, the bulk of younger brother Elliott’s inheritance—despite his high jinks and immorality—remained intact and was being invested through a stock brokerage managed by his uncle by marriage James Gracie.

  Elliott had voluntarily parked himself at a retreat, Château Suresnes, outside Paris, where he somehow learned of the writ of lunacy. He issued a denial to the Herald: “I wish emphatically to state that my brother Theodore is taking no steps to have a commission pass on my sanity, either with or without my wife’s approval. I am in Paris taking the cure at an établissement hydro-therapeutique, which my nerves, shaken by several accidents in the hunting field, made necessary.” His words sounded quite sane and his lawyers in America quickly found a jurisdictional flaw—an incorrect address—in Theodore’s lunacy application.

  Elliott seemed in the clear once again to pursue the life of a wealthy, hard-drinking, adulterous husband. In fact, he was already living with Mrs. Evans in Paris. His brother could not abide that.

  Theodore said he feared for the well-being of Elliott’s children and wife. His own wife, Edith, later admitted a further motive: “I live in constant dread of some scandal attaching itself to Theodore.”

  Boarding a steamer, Roosevelt headed for Europe in January of 1892 to confront his younger brother. They had a brutal meeting in which Elliott tried to laugh off TR’s “stern” lectures, until he finally caved in, “utterly broken, submissive and repentant.” He agreed to sign over two-thirds of his estate to his wife and to undergo two years’ probation with no drinking before earning the right to rejoin his family. His rehabilitation would start with Dr. Keely’s five-week Bi-Chloride of Gold cure in Dwight, Illinois.

  “This morning, with his silk hat, his overcoat, gloves and cigar, E. came to my room to say goodbye,” wrote Mrs. Evans. “It is all over … Now even my loss was swallowed up in pity—for he looks so bruised, so beaten down by the past week with his brother. How could they treat so generous and noble a man as they have. He is more noble a figure in my eyes, with all his confessed faults, than either his wife or brother.”

  Although Elliott returned to the United States, stopped drinking, and was ruled sane later that same year, TR was adamant that his younger brother should not yet see his wife or children. His brother-in-law, real estate investor Douglas Robinson, gave Elliott a job managing properties and staff down in rural southwest Virginia, and Elliott thrived.

  Still dazzling, wife Anna Hall Roosevelt attended a “beauty dinner” hosted by the Turkish minister in Bar Harbor in September 1892, and was regarded as the “belle of the occasion.” Elliott kept writing letters, bragging of his sobriety to his mother-in-law. But a few months later at age twenty-nine, Anna Hall Roosevelt suddenly and shockingly fell ill and lay dying of diphtheria; Elliott wanted to see her one last time but her mother sent a terse telegram to him in Virginia: DO NOT COME.

  Elliott, still exiled from his family by his brother and his mother-in-law, began drinking again; he tipped over an oil lamp while reading naked and severely burned himself. He moved back to New York City and wound up on West 102nd Street living with that same married woman, Mrs. Evans, as “Mr. and Mrs. Elliott.”

  “He is now laid up from a serious fall,” Roosevelt wrote to
his sister Bamie on July 29, 1894. “Poor fellow! if only he could have died instead of Anna!”

  Two weeks later Elliott did die, with only a doctor and his uncle James K. Gracie at his bedside. He had started using “stimulants” again and while suffering from delirium tremens had tried to jump out of a fourth-floor window, but a policeman had restrained him. During his last hours he had called out for his daughter, Eleanor.

  “The terrible bloated swelled look was gone,” wrote sister Corinne to Bamie in London, “and the sweet expression round the forehead made me weep bitter tears … Theodore was more overcome than I have ever seen him—cried like a little child for a long time.”

  In death, the raw emotions finally battered down Roosevelt’s stout moral fortress and he wrote an extraordinary letter.

  [Elliott] would have been in a strait jacket had he lived forty eight hours longer. His fall, aggravated by frightful drinking, that was the immediate cause. He had been drinking whole bottles of anisette and green mint—besides whole bottles of raw brandy and champagne, sometimes half a dozen a morning. But when dead the poor fellow looked very peaceful and so like his old generous, gallant self of fifteen years ago…

  I suppose he has been doomed from the beginning. The absolute contradiction of all his actions and of all his moral—even more than his mental—qualities is utterly impossible to explain.

  For the last few days he had dumbly felt the awful night closing in on him; he would not let us come to his house, nor part with the woman, nor cease drinking for a moment but he wandered ceaselessly everywhere, never still and he wrote again and again to us all sending me two telegrams and three notes. He was like some stricken hunted creature and indeed he was hunted by the most terrible demons that ever entered into man’s body and soul.

  His house was so neat and well kept with his bible and religious books and Anna’s pictures everywhere, even in the room of himself and his mistress. Poor woman, she had taken the utmost care of him, and was broken down at his death. Her relations with him had been just as strange as everything else. Very foolishly, it had been arranged that he should be taken to be buried beside Anna but I promptly vetoed this hideous plan, Corinne who has acted better than I can possibly say throughout, cordially backing me up and he was buried in Greenwood [in the Roosevelt plot] beside those who are associated with only his sweet innocent youth, when no more loyal, generous, brave, disinterested fellow lived.