Viola Roseboro’ (apostrophe intentional), the larger-than-life fiction editor at McClure’s, haunted magazine offices from the 1890s to the Jazz Age. A reader, editor, and semiprofessional wit, she discovered or mentored O. Henry, Willa Cather, and Jack London, among many others. Today she is nearly completely forgotten.

She could often be seen walking through downtown Manhattan alone, recognizable from her preoccupied step, thick dark hair, gray eyes under arching brows, and her purported resemblance to George Sand. She declined to wear corsets and loved cigarettes, and insisted on getting as much fresh air as possible. Instead of occupying a desk, she liked to pack manuscripts into a suitcase and take them to a bench in Madison Square Park, where in all seasons she could be found smoking, reading, and strategizing about how to develop a protégé.

Roseboro’ forged an identity for herself as a tastemaker, claiming she was “plugged in on a stronger current.” Her originality was specific to the city. She was the kind of New York character later embodied in figures like photographer Editta Sherman (the “Duchess of Carnegie Hall”) and literary agent Roz Cole, who represented Andy Warhol and lived at the Waldorf Astoria for more than fifty years.

Roseboro’ did not leave a comprehensive archive, autobiography, or series of cohesive literary works. The most remarkable thing about her, what is worth trying to conjure even now, was her genius at the spoken word. “She was one of the greatest conversationalists of her time,” said magazine editor S. S. McClure, while journalist Will Irwin placed her, in this respect, “at the very top.” Irwin characterized her as a “kind of feminine Dr. Johnson without his touch of pomposity and without a Mrs. Boswell.” The Johnson comparison crops up again and again. Another friend once said of her, “Anybody who does not acknowledge that something is happening when Viola Roseboro’ is talking is stupid.”

Roseboro’—she fiercely defended that apostrophe, reserving her family name, Roseborough, for her life on the stage—was more zealous than many a missionary. She was utterly convinced that books were all that mattered in life. She offered to give one promising young writer her ideas “as you put cloves into an apple you are going to roast.” And yet, though she championed voices who are today seen as canonical and left behind a literary legacy with which few other readers and editors can compete, she died destitute, rarely leaving her rented rooms on Staten Island.

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She was born in 1858, in Pulaski, Tennessee. Her parents, fervent abolitionists, named their delicate only child Viola (Vee-ola), and called her the Pet. Her childhood was itinerant, and her tendency toward croup and “nervous prostration” was treated with classic Victorian remedies: beef tea, mustard water, cold-water treatments, and long stretches in the house reading and dreaming of a future on the stage.

After she graduated from a women’s college near home, her mother urged her to write, while her father fretted that she should marry. Instead, she embarked on a “reading tour” of the South, reaching as far as Cincinnati. For her performances, she would walk onstage and recite poems and monologues, demonstrating her facility with both Southern literature and Scotch dialect. Audiences were rapturous. She had her sights on the real stage, in New York, and after she moved to the city around 1882, she acted in at least two plays, Two Orphans and The Lights O’ London. But her health was fragile, and she abandoned acting after a bout of pneumonia. The only thing she would ever have in common with Sarah Bernhardt, she wrote to her mother, was a liking for eating apples in bed.

Her pivot to a literary career was swift and confident. She got a weekly column from the Nashville Daily American, and a press pass that gained her entry to cultural events across the city. Five years after her move to New York, she was contributing to The Century, The Cosmopolitan, The Daily Graphic, and working on her first novel. Richard Watson Gilder, editor of The Century, folded her into his family and circle of friends, and she also frequented artists’ studios, especially stained-glass artist and muralist John La Farge. She was hired as a reader at a literary syndicate run by S. S. McClure, and moved to the fiction desk at his magazine, McClure’s, when it launched in 1893.

At McClure’s, she was known to her colleagues as Rosie. She became close friends with rising investigative journalist Ida Tarbell while both were on staff at the magazine, and Tarbell wrote of her: “By good fortune McClure’s in this period happened upon a reader of real genius—Viola Roseboro—the only ‘born reader’ I have ever known. … Her judgments were unfettered, her emotions strong and warm, her expressions free, glowing, stirring, and she loved to talk, though only when she felt sympathy and understanding. … An unsleeping eagerness to find talent and give it a chance, and secondarily, she said, to enrich the magazine, made every day’s work with the unsifted manuscripts an adventure. If she found exceptional merit that was also suited to McClure’s, she might weep with excitement.”

On one famous occasion, Rosie hurried to the editor with tears in her eyes to insist on the publication of Booth Tarkington’s The Gentleman from Indiana. She struck up a correspondence with O. Henry—the pseudonym of William S. Porter, who was then serving time in the Ohio Penitentiary—and McClure’s featured his first published story under that name, “Whistling Dick’s Christmas Stocking,” in 1899.

To Willa Cather, who joined McClure’s in 1906, Rosie was “my first critic.” Reportedly, on reading the manuscript for My Ántonia, she told Cather, “[You] have told your novel through the wrong character’s eyes, from the wrong point of view. Have you the courage to throw the [manuscript] away, and sit down and re-write it from [Jim Burden]’s point of view, you have a great book.” Cather heeded her words. After its success Roseboro’ often gave the book to visitors, calling it “one of the books of the world” and “wholly perfect.”

Many of Rosie’s authors are no longer read today, but were acclaimed in their time: Josephine Daskam, George Madden Martin, Myra Kelly, Harvey J. O’Higgins. Others, like Rex Beach, are hovering on the edge of total obscurity; still others are experiencing a moment of resurrection, as with recent reissues of Booth Tarkington’s major novels The Magnificent Ambersons and Alice Adams.

Her mentorship could be prickly, and her critiques could be jarringly personal. She did not entertain any notions of separating the writer’s character from the work. As she told one resistant young writer, “It is nonsense to think you can get criticism on manuscripts that is not criticism on yourself—if it has the least depths or is worded so as to be useful.” Some received her involvement with “elation”; others distanced themselves. Her attachments and convictions were often too fiery to appeal for long, and her temper was notoriously short.

Books were Rosie’s life, and there were a handful that formed her foundation. She knew Shakespeare back to front, though her preferred play depended on her mood and stage of life. When she was older, she enjoyed King John especially because, as she wrote to a friend, “I do find the Bastard a most strikingly alive and individualized being, not composed, made by reflection, but delightful principally because he is a kind of miracle of just being born all there, as if Shakespeare did not know what he would say next until he said it to him.” The Iliad and the Odyssey awed her, and as a minister’s daughter, she had entire passages of the Bible by heart.

She loved Whitman, Emerson, and Housman, and whenever anyone came to her she would press a book on them to take away. For Rosie books were the connective tissue that gave relationships meaning, instead of the reverse, as it is for most of us. “About all the companionship I can have now is talk in letters about books that I and my correspondents have both read,” she wrote a friend, when her eyesight was bad.

The one work she cared for most of all, though, was surprisingly unliterary: The Mystic Will, by Charles Leland, a self-help volume focused mainly on willpower and visualization. A kind of prototype of The Secret, it was behind Rosie’s frequent advice to younger people: “Become what you are.”

What was Rosie herself, besides a live wire with a tendency to Wildean pronouncements, if Wilde had been a New Yorker? One could dwell only on her recorded quotes and come away with riches. Of Lillian Wald, celebrated founder of Henry Street Settlement, Rosie remarked, “She is entirely uncorrupted by a lifetime of doing good.” In describing a woman she disliked, she said her hair looked “like rats had sucked it.” Once she remarked that “the greatest defect of modern civilization was the absence of any place where one could adequately insult people. Either you were in the relationship of guest and hostess or you were both guests of someone else, and when you chanced upon each other at the Grand Central Station, there was no time for you were dashing for a train.” (She would, it is clear, have adored Twitter.)

She never abandoned staginess, and friends often reported that her large presence made her seem much taller than her actual five-foot-three. She rarely revealed her true age—“Prenatal memory prompts the reference,” she once told a colleague who asked about a long-past incident. Her electric spirit hardly dimmed in middle age. One young writer described her as a “great table thumper. I have seen her make the silverware at the old Lafayette jump, and the cups at the Brevoort rattle in their saucers!”

Her personal eccentricities multiplied over the years. She lived alone, or boarded in a family home; friends report no knowledge of a romantic entanglement. She dreamed of having a son, however, and periodically “adopted” young men in her circle. Men were her preferred company; she didn’t believe in women’s suffrage. But she didn’t care to be ladylike, she wore cheap, slouchy clothes and rolled her own long, skinny cigarettes. Unconventionally, but mainly because she was so unsuited to cooking, she ate mostly raw food. Some of her quirks put her ahead of her time; she was evangelical about yogic breathing and staying hydrated, and she often carried an old gin bottle full of water around the city. When someone once protested that it couldn’t be healthy to sip old water throughout the day, she angrily replied “Well, damn it, die!”—an expression that rippled outward among her writer friends, a byword for Rosie-ness. In the summer, her preferred way of living was to move to Provincetown, on Cape Cod, where she would sleep on her porch.

After McClure’s floundered in the 1910s, she struggled financially. She became increasingly deaf, and her hands, too, became worn out by the strain of rewriting others’ drafts and sending long editorial memos. Despite her money troubles, she couldn’t resist anonymous acts of charity and frequent social outings. Touched by the story of a spinster who had died in Italy, she paid for the perpetual care of the woman’s grave. Even in her eighties, she would occasionally leave her rooms in Staten Island, take a friend and a pillow, and go downtown to see up to four picture shows at a time. She knew every inch of the Metropolitan Museum, but she didn’t like concerts. Whenever anyone came to her, she entertained them with sherry outdoors if it was fine, or tea by her little Franklin stove if it was cold. Her own favored drink while she was working was a mug of half-coffee, half-chocolate.

She wrote, too—not only letters upon letters in her “huge, blind” handwriting, but short stories and articles. She published the novels Old Ways and New (1892), The Joyous Heart (1903), Players and Vagabonds (1904), and Storms of Youth (1924). Her prominence as a talent whisperer and literary booster meant few reviewers were willing to really criticize her. One confessed of The Joyous Heart, “Candidly, I love the writer, revealed through the book, better than the book itself, albeit it has my warm heart.”

Again and again, others remarked on her regal intensity and expressiveness. Frances Perkins, a labor-activist friend who became the first woman appointed to the U.S. Cabinet, wrote, “Of course I remember her vividly—her conversation, her attitudes, her courage … Miss Roseboro’ was essentially an expressive person. She couldn’t bear to enjoy … things alone, and that is why she would ask me to go along with her because she said, ‘I like to go with you because you enjoy having me talk about it.’” In later life Viola Roseboro’s close friend Gertrude Hall said to her: “To you the gods have granted a boon … to command instant attention and interest the very instant you care to. It is like sovereignty.” The McClure group liked to say her initials stood for Viola Regina.

There is a rumor that when Rosie died, in 1945, she was working on a memoir of the people she’d known and loved titled Let Me Tell You. If it ever existed, the manuscript is likely lost. It’s tantalizing to imagine the coda Rosie would have written for herself, how much she would have exceeded the last line of her New York Times obituary: “She was unmarried.”

Stephanie Gorton is the author of Citizen Reporters: S. S. McClure, Ida Tarbell, and the Magazine that Rewrote America, out this month from Ecco.