During Oscar Wilde’s speaking tour of America in 1882, the front two rows of the crowded Boston Music Hall were conspicuously empty. As Wilde took the stage, sixty Harvard students marched into the hall clutching sunflowers and wearing the high-camp, aesthete-approved attire of knee breeches, black stockings, wide cravats, and Wildean wigs. Wilde may have anticipated their prank and was conservatively dressed in a simple coat and trousers. He pretended to overlook them before pulling back in mock surprise. He began: “As I look around me, I am impelled for the first time to breathe a fervent prayer, ‘Save me from my disciples.’ But rather let me, as Wordsworth says, ‘turn from these bold, bad men.’”

Chanler rarely stayed in one place for more than a moment, moving his household from the family estate on the Hudson to Rome, Newport, Washington, upstate New York, and Rome again before settling further upstate at Sweet Briar Farm in Geneseo, New York.

The leader of those bold young men was Winthrop Astor Chanler, son of the congressman John Astor Chanler and one of the famous eight surviving Astor orphans. “Wintie” was left parentless but not penniless at age fourteen. Educated at Eton and Harvard College and possessing a “lively rather than disciplined” mind, he was not a model student, but he read enough Latin, French, and English literature to complete his gentleman’s education in “charm, amenity, and good taste,” as his wife Margaret Terry Chanler noted. His lifelong friend Owen Wister, the founding father of American Western fiction, thought Wintie hailed from a bygone era: he could credibly sit for a portrait of Sir Walter Raleigh, Wister argued, and if he had “lived in the age to which so much of him belonged, he would have sailed with Drake or Raleigh any day at a moment’s notice.” Chanler rarely stayed in one place for more than a moment, moving his household from the family estate on the Hudson to Rome, Newport, Washington, upstate New York, and Rome again before settling further upstate at Sweet Briar Farm in Geneseo, New York. A visitor once dropped by the family estate on the Hudson expecting to find Wintie. “He’ll be here tomorrow,” said one of his sisters, “at least if he hasn’t gone to Pawtucket, or Portland, or Fitchburg, or Atlanta . . .” Another sister chimed in: “Whatever Wintie does, his conscience sits looking on, beating happy applause.” From each new home base, he launched new expeditions: hunting mouflon sheep in Sardinia and elk in the Rockies (sharing part of the train ride west with Mark Twain), Rough-Riding in Cuba with Teddy Roosevelt, fox-hunting with the Meath Hounds in Ireland, and serving as General Pershing’s aide-de-camp in the Great War.

“Wintie always made light of hardships met with in the pursuit of adventure (the form asceticism takes with sportsmen),” wrote his adoring wife in The Letters of Winthrop Chanler, which she privately printed. As a houseguest during their courtship in Rome, he silently endured the bites of Roman fleas. Cruise-ship porters were amazed that he could cross the Atlantic as an honored guest in the state room and return cheerfully in a shared third-class upper bunk. During an overnight train breakdown in the “howling wilderness” of Colorado, Wintie and his fellow passengers stoked an enormous bonfire beside the tracks and sang hymns in the moonlight.

Wintie was not the only adventurer in the family. His younger brother Willie, once come of age, defied his guardians by leaving Harvard early to become a big game hunter in Africa. When the two set off together on an ambitious search for oil in Morocco, their nervous London outfitter approached the American ambassador that was accompanying the pair. What would happen should his client be killed in the wild? The ambassador assured him that if Mr. Chanler died he would be paid immediately by the family trust; if Mr. Chanler came back alive, however, he would have to wait a long time for his wages. The search failed. In another project, Wintie and his older brother Armstrong attempted to build a hydroelectric plant supporting a cotton mill and small village on the Roanoke River in North Carolina. To design the cotton mill they commissioned the Beaux-Arts architect Stanford White, who knew as little about mills as the Chanler brothers did.

Despite his attempts at business, Wintie remained more marksman than free marketeer and became a founding member of Teddy Roosevelt’s Boone and Crockett Club along with his friends Austin Wadsworth, Grant La Farge, Owen Wister, and Charles Deering. Just for amusement, Wintie often accompanied Roosevelt on his legendary midnight raids as the police commissioner of New York City. Wadsworth invited Wintie to his upstate homestead in Genesee Valley, where he risked injury to body and ego in rounds of “singlestick combat” with Roosevelt. “I am certain to be licked,” he writes in a letter to his wife, “or, in the very improbable event of a victory, to be locked up in the jail overnight.” The 1911 Encyclopedia of Sport and Games provides additional context for this forgotten sport: “Singlestick, or cudgel-play, is, moreover, an honest, manly old English sport, which should rather be encouraged than allowed to sink in to oblivion.” In the White House, Roosevelt faced off in singlestick combat against his old Rough-Riding pal Major General Leonard Wood to rehabilitate a leg injury suffered early in his presidency. As late as 1898, singlestick training was practiced aboard the USS Maine despite the disappearance of cutlasses and the virtual impossibility of a modern capital ship being boarded.

When an explosion sank the USS Maine in Havana Harbor, Roosevelt resigned from his position as Assistant Secretary of the Navy and helped to organize a volunteer regiment sent to Cuba. “I really think he is going mad,” writes Chanler; “the President has asked him twice as a personal favor to stay in the Navy Dept., but Theodore is wild to fight.” But Chanler misjudged the effect of Roosevelt’s impulsiveness on future prospects: “Of course this ends his political career for good.”

Worried that the American naval blockade would quickly starve Spain out of the war before he could fire a shot, Chanler raced to join Roosevelt’s Rough Riders. He found himself among friends. “We drew recruits from Harvard, Yale, Princeton, and many another college,” wrote Roosevelt in his memoir The Rough Riders; “from clubs like the Somerset, of Boston, and Knickerbocker, of New York; and from among the men who belonged neither to club nor to college, but in whose veins the blood stirred with the same impulse which once sent the Vikings over sea.” Roosevelt, Chanler, and their fellow officers drank a toast before disembarking in Cuba: “May the war last until each is killed, wounded, or promoted!” Their landing was anticipated and they found themselves immediately in a firefight with a well-hidden enemy. Pinned down for several days and nights in a ditch as bullets zipped overhead, they felt the full effect of tropical heat and humidity while running low on food and fresh water. “One morning when they had about touched zero,” Owen Wister recalls, “Chanler rose up somewhere in the cactus and remarked in a tone of cheery conviction: ‘This is no place for a married man.’” The men rallied to participate in the victory in Cuba. As predicted, the war ended quickly, but not before Wintie took a bullet in the arm. It missed bone and artery, so he was shipped home to recover at Stanford White’s vacant house in Manhattan, lifting weights to build strength in his injured arm and lifting flutes of Pol Roger to his lips with the other.

He ended the war in Italy armed only with “a knife and a bitter tongue trained to curse horridly in four languages, English, French, Italian, and Boche [German].”

The Chanlers moved at this time from Newport to Sweet Briar Farm in Livingston County in upstate New York. Wintie became Master of the Hounds at the Genesee Valley Hunt Club, while his wife built the Chapel of St. Cecilia on their homestead. But their peaceful country life was interrupted by America’s entry into the Great War. General Pershing, the Commander in Chief of the American Expeditionary Forces, requested two good worldly men familiar with French culture as his personal aides. William Corcoran Eustis and Winthrop Chanler were offered the job despite being well past the typical age for military service. (Wintie was 53.) Neither of them seemed likely to pass a medical examination, but their examiners shielded their various ailments and injuries in medical jargon impenetrable by army bureaucrats. Pronounced “hunting sound,” the two old sportsmen went to war. “I feel like a Roman Centurion,” Chanler wrote from France, “and ready to bully my subordinates!” He ended the war in Italy armed only with “a knife and a bitter tongue trained to curse horridly in four languages, English, French, Italian, and Boche [German].” In peace time, his wife cruised the Aegean Sea with Edith Wharton while Wintie toured Crete with an old wartime friend. (He and Wharton never got along well.) He fell ill and returned to Sweet Briar Farm in declining health.

The Curé d’Ars, who was not as well traveled as the Chanlers, said that not every saint begins well but that they all end well. After a life of infamy, Oscar Wilde was reconciled to the Catholic Church on his deathbed. Wintie often told his wife that he too wished to die a Catholic, like her, but long delayed his entrance in the Church. “When my head is so far from the ground on my last fall,” he said while holding two fingers inches apart, “I shall become a Catholic.” One day he and his wife went out for a ride. “Let’s have a little canter,” he said, then collapsed in the saddle. A priest was called and Wintie received the Last Rites before dying in bed. This Astor orphan was comforted to know that “in my Father’s house there are many mansions” and that a place was now prepared for him.

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