The Tragic Life of Kermit Roosevelt & the Burden of Legacy

Supported by a crew, Teddy Roosevelt, Kermit, and a Brazilian explorer, Candido Rondon, canoed the Rio da Duvida—“River of Doubt”—a notoriously dangerous and little-explored waterway of the Amazon. Two months into the trip that began in December 1913, the president wrote to his sister, finally acknowledging Kermit’s relentless quest to emulate his famous father.

“Kermit causes me much concern; he is altogether too bold, pushing daring into recklessness…the fear of some fatal accident befalling him [is] always a nightmare to me.”

The concern was too little, too late.

Theodore Roosevelt, the 26th president of the United States, enthusiastically promoted what he called “the strenuous life”—a state of heightened physical and psychological engagement inculcated in him by his father, also Theodore, an investment banker with the family firm Roosevelt and Sons.

In 1871, young Teddy, 13, was a weak, awkward, and asthmatic child who wore glasses, then the mark of a milquetoast. To invigorate the boy, Theodore Sr. and his wife Martha set up a gymnasium on the second floor of their townhouse on East 20th Street in Manhattan. Teddy, who was home-schooled, added to his routine lifting weights, using the horizontal bars, and punching a heavy boxing bag.

When bullies ragged him, his father hired a professional pugilist to train him to defend himself. By 16, young Roosevelt was spending hours working out. He devoted his summers to running, hiking, hunting, and rowing. Being of old money and high social status, the Roosevelts could have coasted on their family fortune, but the father and son spurned the comfortable path—in the former’s case, leading to an untimely death at 46.

The son attended Harvard College, where he met Alice Hathaway Lee. They married shortly after his graduation in 1880. Alice died in 1882 from an undiagnosed kidney failure two days after giving birth to a daughter, also Alice. Distraught, Theodore threw himself into public affairs, and that same year, his attacks on corruption gained him a seat in the New York State Assembly. He toggled between politics and ranching in the Dakota Badlands. In 1885, he rekindled a youthful romance with Edith Kermit Carow, three years his junior. The couple wed in London, England, on December 2, 1886. That winter, severe weather wiped out Theodore’s cattle, prompting him to sell off his Western interests.

In 1887, Roosevelt and Edith took up residence at Sagamore Hill in Oyster Bay, New York. Theodore spent the next few years writing and publishing to recuperate his losses from the Dakota venture. By decade’s end, he authored nine books, including the multi-volume history of the American West, The Winning of the West.

In 1889, Theodore took a step up in his career by accepting the US Civil Service Commissioner position in Washington DC. In his six-year tenure at the helm, Roosevelt rooted out administrative corruption through reforming the spoils system into one based solely on merit.

In August 1894, while living with his family in DC, Theodore was once more plagued by tragedy when his younger brother Elliot, 34, lost his drawn-out battle with alcohol and morphine addiction. Frequent bouts with depression resulted in a casual drinking problem in young adulthood, morphing into alcoholism by the time he was thirty.

Elliot had abandoned his wife and three children, the middle girl being Eleanor Roosevelt. Elliott spent a short stint in an asylum on a writ of lunacy before moving to New York City under an assumed name to live with his mistress. The ostracized Roosevelt died a few days after complications from an unsuccessful suicide attempt.

Theodore later wrote that Elliott “was like some stricken, hunted creature” who was pursued by “the most terrible demons that ever entered a man’s body and soul.”

Following his brother’s death, Roosevelt and his family returned to Sagamore Hill. In 1895, he accepted the position of New York City’s police commissioner. Theodore’s love for the job sustained him, and the press quickly gave him the moniker “Teddy the Scorcher” for his relentless fight against corruption.

As Roosevelt’s political stock rose in the Republican Party, President McKinley appointed him the Assistant Secretary of the Navy in 1897, a post he resigned to lead the Rough Riders cavalry unit in the Spanish-American War. In 1900, Roosevelt’s popularity was such that McKinley, running for reelection, chose him as his running mate. Not quite a year later, an assassin’s bullets put Theodore Roosevelt, 42, in the White House.

Edith and Theodore Roosevelt had six children—four sons and two daughters, the eldest being Alice, Theodore’s daughter from his first marriage. She was joined by Theodore Jr., Kermit, Ethel, Archibald, and Quentin.

Teddy adored his children and was their most valued playmate. He led them on hikes, hunts, swims, and horseback rides. Under fire on San Juan Hill, he had collected spent cartridges to bring home as souvenirs for them. He told the boys that defending and advancing the nation ranked highest among Americans’ every duty and privilege. He once said he would rather his children “die than have them grow up weaklings.”

Her father’s ascent to the presidency made Alice, 17, a celebrity and fashion plate. Outspoken and unconventional, she thrived on attention. Stepmother Edith cautioned daughter Ethel, 10, not to model herself after her half-sister. The Roosevelt boys—the youngest lads to live in the White House since Abraham Lincoln’s sons—made for good newspaper and magazine copy. Reporters wrote of the lads transporting their favorite pony, Algonquin, on the presidential mansion’s elevator, frightening visiting officials with a four-foot snake, and dropping water balloons onto White House guards’ heads.

Emulating their father, Teddy’s boys strove to be honorable, fearless, and uncompromising—but also, like him, they were not exempt from troubles. Eldest son Theodore Jr. served in the New York State Assembly, became undersecretary of the Navy, and unsuccessfully ran for the governorship of New York in 1924, losing to Al Smith, a candidate endorsed by his cousin Eleanor and her husband, Franklin. He served in both World Wars—dying of a heart attack one month after landing at Normandy on D-Day.

Archie, a boisterous child and avid animal lover, also served in the wars—he was badly wounded in the great war—after which he established a successful brokerage house in New York City.

Youngest son Quentin was the golden child—funny, fearless, academically gifted, mechanically brilliant—and doomed to die young at war.

All the boys looked up to their father, but Kermit most fully embraced his ethos. Like his dad, a sickly child drawn to the strenuous life, he nonetheless differed from his parent. Resembling Theodore’s late brother Elliott, Kermit was irritable, easily bored, and given to depression. When an elementary schoolmate mocked Kermit’s father, then at war in Cuba, he beat up the naysayer.

Theodore fostered in Kermit a love of languages, the humanities, and poetry, balanced by adventures that Kermit anticipated enthusiastically. By 18, as a Harvard freshman, he was athletic, an avid reader of history, a daring outdoorsman, and a curious traveler who, in time, mastered many languages, including Greek, French, Portuguese, Swahili, Arabic, Hindustani, Urdu, and Romany.

When Theodore Roosevelt, looking to recharge upon leaving the presidency in 1909, decided to go on safari in Africa under the auspices of the Smithsonian Institution, he enlisted Kermit, just finishing his first year at Harvard, as his fellow hunter and confidant. A skilled horseman and a fair shot, the son suspended his studies to participate in the Smithsonian-Roosevelt Expedition.

He proved industrious, independent, and fearless. Comparing him to the timid boy he had been in a letter to Theodore Jr., Theodore wrote that Kermit “is a little too reckless and keeps my heart in my throat, for I worry about him all the time…he is a bold rider, always cool and fearless, and eager to work all day long.”

Theodore’s letters mentioned Kermit running down and singlehandedly killing giraffes and hyenas. In one episode, “he stopped a charging leopard within six yards of him after it had mauled one of our porters.”

Kermit and a guide disappeared into the bush for two months to hunt lions, prompting his father to write, “When Kermit shows a reckless indifference to consequences when hunting, I feel like beating him.”

Returning to Harvard and graduating in 1912, Kermit impressed his father by relocating to Brazil, whose undeveloped interior was a massive mystery. He worked for the Brazil Railway Company and built bridges for the Anglo-Brazilian Iron Company. He narrowly escaped death when a collapsing span dropped him hundreds of feet and buried him in debris. He met and fell in love with Belle Willard, daughter of the US Ambassador to Spain. Kermit’s father, again taking to the wild to recharge—this time after a crushing defeat as a third-party candidate for president in 1912—invited Kermit on a 1913-14 river journey in a remote region of Brazil.

Originating as a series of lectures in Argentina, Brazil, and Chile, the project evolved into a leisurely specimen-gathering expedition well-suited to a man of advancing years and middling health. Financed by the American Museum of Natural History, the trip again changed at the suggestion of Brazilian Minister of Foreign Affairs Lauro Muller. Now, Theodore Roosevelt and Brazilian explorer Candido Rondon would explore the uncharted River of Doubt. Roosevelt encouraged his son to postpone his wedding and light out with him into the unknown. Kermit agreed.

From the beginning, the Roosevelt-Rondon Scientific Expedition tested Kermit’s devotion to his father’s “strenuous life.” Participants were constantly sick, injured, and feverish from malaria and insect bites; Theodore, at times, was near death.

Rather than lightweight North American-style canoes, they were paddling hollowed-log dugouts, heavy but also fragile, forcing frequent stops to replace vessels. Moving at a crawl, supplies dwindling, the party looked to the elder Roosevelt for motivation that wound up coming from his son.

Staggered by malaria, the younger Roosevelt pressed on. His hunting, tracking, and canoeing skills proved invaluable. He refused quinine for his own fever, aches, and diarrhea lest there not be enough of the drug for his father. Only when Kermit was too weak to resist could the expedition doctor inject him and restore his health.

Canoeing with a guide, Kermit attempted to paddle across the river at a point his father thought too dangerous. The current overturned the dugout, hurling its occupants into the water and dragging them under just upriver from a waterfall. The guide drowned. Kermit, blinded and choking, careened over the falls and, despite his waterlogged clothing, kept afloat until he could pull himself onto shore. Drenched and exhausted, he seemed unapologetic about his escapade and his companion’s death.

In his journal that night, Theodore acknowledged that his son had a “very narrow escape.” Had they lost Kermit, he admitted, he did not think he could have survived having to deliver “bad tidings to his betrothed and to his mother.” Though Kermit’s disregard for safety rattled Theodore, he could not hide his pride. “Kermit has really become not only an excellent hunter but also a responsible and trustworthy man, fit to lead,” Theodore wrote.

Kermit and Belle Willard married in 1914. The couple settled in Argentina, where Kermit secured employment as an assistant manager for the National City Bank in Buenos Aires. The young Roosevelts stayed in South America until 1917, when Kermit could no longer withstand the United States’ isolationist policy towards World War I.

Having grown up hearing his father extol combat as a mark of manhood, he initially enlisted in the US Army in 1917 but, itchy to fight, resigned his commission and joined the British Army. Kermit’s wife moved to Europe with her husband, first to Britain, then to France, where Roosevelt was promptly assigned a position on the staff of General Maud, operating against the Turks in Mesopotamia.

Kermit was transferred to the front with the Motor Machinegun Corps. He was employed with the mounted cavalry unit raiding Turkish forces, quelling Arab uprisings, and participating in major attacks on the Euphrates and Persian front at Kifri.

Speaking of his experiences in the Rolls Royce armored car, Kermit recalled “splinters of lead [coming] in continuously,” with “the great heat of the summer,” making the inside of the turret “a veritable fiery furnace.”

In the spring of 1918, Kermit received his desired transfer to the American Expeditionary Force. In a phrase of the day, he had a good war, serving with distinction in the Meuse-Argonne Offensive that ended the conflict on November 11, 1918.

Kermit’s three brothers also had taken up arms. Wounded in France serving with the US 1st Infantry Division, Archie accepted a discharge with full disability. Ted Jr., gassed and wounded in the AEF, barely emerged from the conflict alive. Quentin died at 20, shot down over France during the Second Battle of the Marne in July 1918.

His grief-stricken parents retreated to Islesboro Island, Maine, where the ebullient Theodore collapsed into himself, writing few letters, hardly speaking on the telephone, and staring at the sea for hours.

Writing to fellow Rough Rider Bob Ferguson, Theodore Roosevelt clung to his oft-professed values. “It is bitter that the young should die,” he told Ferguson. “[yet] there are things worse than death, for nothing under Heaven would I have had my sons act otherwise than as they acted.” He never recovered from Quentin’s death, himself dying in January 1919.

Kermit carried on. He and Belle had four children. In 1919, the family settled in New York, where Kermit started building his shipping empire, the Roosevelt Steamship Company. Throughout the 1920s, his company’s consolidation of many smaller shipping businesses eventually made Kermit the manager of eight steamship companies operating as far as Australia and the Far East.

Periodically leaving his family in New York, Kermit, chasing more thrills, undertook numerous expeditions, including, with brother Ted, a 1925 trek through the uncharted Himalayas and a 1928-29 Asiatic foray.

Like his father, Kermit also turned to writing. His book, War in the Garden of Eden, detailed his World War I experience in Mesopotamia, while his East of the Sun and West of the Moon, written together with his brother Ted Jr., chronicled their later Himalayas and Asian hunting excursions. In a collection of essays describing his life travels, The Happy Hunting Grounds, Kermit evoked his father’s creed of a strenuous life when he opened with, “It is when men are off in the wilds that they show themselves as they really are.”

The 1930s witnessed the emergence of another Roosevelt – Franklin Delano, a Democrat. Even though he was married to Theodore’s niece Eleanor, FDR was only a distant cousin of the Oyster Bay clan and not highly regarded by them. Ted Jr. dismissed Franklin as a “maverick” who “[did] not have the breed of our family.”

When Franklin was elected President in 1932, Ted Jr. was appalled to learn that Kermit had voted for the Democrat. Kermit and Belle were friendly with the now governor of New York and his wife, Eleanor. The relationship stemmed from Franklin and Kermit frequenting the same social circles and New York City’s meeting clubs of world travelers, bankers, and heads of business and industry.

While the Great Depression saw the rise of Franklin and Eleanor, Kermit and Belle’s fortunes took a turn for the worse. The Depression, having severely affected the shipping industry, sapped Kermit’s finances and set him back on his heels.

Although still employed and working throughout the decade, the economic pressures of a failing business forced Kermit and Belle to balance their investment losses and living expenses against their low income. By 1933, they overdrew their Fifth Avenue Bank account on so many occasions that they suspended writing checks altogether.

The unpaid bills forced the couple to give up many things they once took for granted. Not even a savings of $20 for dropping Belle’s membership in the Child Study Association of America was too trivial. In 1937, Kermit canceled his subscription to the New York Times and resigned from the Tennis and Racquet Club and the Explorers Club.

Kermit’s already fragile temperament and predisposition to mental depression began to put a strain on the family. Unable to afford to travel and deprived of topics to write about added another layer to his malaise. As the unpaid bills stockpiled, Roosevelt drank and ran around on Belle, disappearing for weeks, returning half-drunk to apologize, only to repeat the pattern.

The onset of another war offered redemption and distraction. Thinking of reprising his first martial experience, in 1940, Kermit importuned British prime minister Winston Churchill for a commission. Churchill assigned him command of a unit among those sent to repel the Soviets from Finland and then to North Africa to fight the Germans. He mocked the monotony of patrols and drills in Africa, backsliding into drink. In early 1941, the British Army ordered him to England for a medical discharge.

Kermit returned to Belle a physical and mental wreck. His efforts to kick alcohol led to a dependency on paraldehyde, a drug used to cure acute alcohol intoxication. Liver enlarged, teeth ruined, stomach churning with flareups of malaria, Kermit was mired in depression. In June 1941, he vanished again. Belle, who was close with FDR and Eleanor from before the Depression, asked the president to send the FBI after him.

Within weeks, agents found him in New York City, bruised from a beating by a cab driver. Archie Roosevelt committed his older brother to a sanitarium in Hartford, Connecticut. Released that autumn, Kermit again disappeared, this time with mistress Carla Peters. In early 1942, the FBI found the couple in California, Kermit a stumbling drunk.

Instead of bringing him home to New York, Archie and Belle booked Kermit into the sanitarium in Hartford while they plotted a longer-term solution. Archie and Ted Jr. engineered a US Army commission for their troubled sibling. The US Army Air Corps assigned Kermit to a base at Fort Richardson near Anchorage, Alaska. He was to establish and train a territorial militia of Indigenous Alaskans meant to function as an insurgent force should the Japanese, who had seized several of the Aleutian Islands, attack mainland Alaska.

Kermit briefly regained a sense of purpose until liver and stomach trouble caused internal bleeding. After a hospitalization, he returned to Fort Richardson in May 1943. On June 3, 1943, after saying goodbye to a friend, he retired to his room, sat on the edge of his bed, put his .45 pistol under his chin, and pulled the trigger. He was buried at the fort’s cemetery beneath a regulation-issue headstone. He was 53 years old.