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About The Book

This glittering, “wild romp of a story, boldly and beautifully told” (Neal Thompson, author of The First Kennedys) explores the darkly intertwined fates of infamous socialite Ann Woodward and literary icon Truman Capote, sweeping us to the upper echelons of Manhattan’s high society—where falls from grace are all the more shocking.

When Ann Woodward shot her husband, banking heir Billy Woodward, in the middle of the night in 1955, her life changed forever. Though she claimed she thought he was a prowler, few believed the woman who had risen from charismatic showgirl to popular socialite. Everyone had something to say about the scorching scandal afflicting one of the most rich and famous families of New York City, but no one was more obsessed with the tale than Truman Capote.

Acclaimed for his bestselling nonfiction book In Cold Blood, Capote was looking for new material and followed the scandal from beginning to end. Like Ann, he too had ascended from nobody to toast of the town, but he always felt like an outsider, even among the exclusive coterie of high society women who adored him. He decided the story of Ann’s turbulent marriage would be the basis of his masterpiece—a novel about the dysfunction and sordid secrets revealed to him by his high society “swans”—never thinking that it would eventually lead to Ann’s suicide and his own scandalous downfall.

“A 20th-century morality tale of enduring fascination” (Laura Thompson, author of The Heiresses), Deliberate Cruelty is a haunting cross between true crime and literary history that is perfect for fans of Furious Hours, Empty Mansions, and Midnight in the Garden of Good and Evil.


If Ann Woodward had resolved to live a quiet life in Europe, where she could mourn her late husband, Billy Woodward, far from the madding crowd of the American press, the town of Saint Moritz, high in the Swiss Alps, was certainly an unusual place to retreat to. Renowned for its winter sports, popular as a spa hamlet, and exclusive as a community where entertainers, celebrities, and assorted socialites gathered, Saint Moritz was a lesser European sun around which various society moons revolved. While summer tourism was popular, it was in winter that this small city shined. Luminaries descended in head-to-toe furs in the daytime and flashy jewels at night, their diamonds and bangles competing with the glittering snow. In the fall of 1956, Ann Woodward was once again the center of attention as she sat down for dinner at one of Europe’s most elite restaurants.

Back in the United States, those familiar with Ann Woodward—and lately there were few who had not heard of her, whether over lunch at the Colony on New York’s Upper East Side, or on the front pages of tabloids—believed that she had been banished to Europe by her formidable mother-in-law, Elsie Woodward, and was now likely leading a lonely life, without family or friends, much less a lover, with plenty of time to reflect on the transgressions that had forced her into exile.

But as Truman Capote watched her from a table across the restaurant, he saw that she was not the solitary widow they expected. Capote was not only surprised to see her in this particular location, but astonished to see her in the company of a man, which was a cause for raised eyebrows, considering that she had entered widowhood by her own hand not so very long ago. But Ann Woodward did not seem rattled by the patrons staring with obvious disdain as she exchanged languorous looks with her companion.

Truman recognized the man she was with: Claus von Bülow. A noted womanizer, the tall and handsome von Bülow had committed himself to the effort of charming a long list of social contacts and prided himself on his cultivation of illustrious connections—much as Ann herself had done during her early years in New York. Ann found in von Bülow an amusing companion, younger than herself, a man with a past as colorful as her own, if not more so. The rumors surrounding him were dark: that he was a necrophile; that he had killed his mother and stashed her body on ice; that somehow, he was still embroiled in espionage; that as a youth he had attended Hermann Göring’s wedding. Von Bülow could rebut most of the gossip if he ever found himself in the mood to explain, which was rare. Most of the time he shrugged away the stories with a smirk, which made him even more beguiling to many.

In later years, long after Ann Woodward had come and gone from his life, Claus von Bülow would be indicted for the attempted murder of his wife, Sunny, whom he married in June 1966, and who would spend twenty-seven years and eleven months in a coma after it was suspected Claus von Bülow attempted to kill her by injecting her with sedatives and insulin. The position he would find himself in was not unlike Ann Woodward’s, and further solidified his bizarre connection to her.

Truman Capote had, of course, heard all about Billy Woodward’s murder when it happened back on Long Island. On November 15, 1955, not two weeks after Billy’s death, Truman had written to his friend the photographer Cecil Beaton that “Ann Woodward continues to occupy the front pages—but those who discuss it have had to move to L’Aiglan since Mr. Soulé closed the Pavillion. L’Aiglan has upped its prices.” But Capote most often frequented Henri Soulé’s restaurant La Côte Basque, which had opened in the late 1950s and was located just across the street from the Saint Regis Hotel in New York City. There, Truman’s eyes often widened in mischief and delight when he and his friends told the most cutting jokes and dished the other diners, including Ann Woodward, who was not only a patron but also lately a topic of discussion.

Truman Capote found Ann Woodward interesting. Indecorous, perhaps. Certainly audacious for showing herself in public so soon after being accused of killing her husband, and with a man who appeared to be a lover. He continued to stare, but at a certain point he was compelled to get up from his table and walk toward Ann Woodward. He must have also had a suspicion that the encounter, however short, would annoy her, if not downright distress her, which likely increased his delight at his own mischief. As he arrived at the table, Ann immediately got up from her chair, angry that she should have been disturbed during her meal. A short conversation followed, during which, apparently, Ann called Truman “a little fag.”

That was not the first time that Truman Capote had been insulted for his sexual orientation, nor would it be the last. But with the insult coming from Ann Woodward, an accused killer, he took more offense to the jab than he usually did. He returned the slur by wagging his finger at her and calling her “Mrs. Bang Bang,” a moniker that would stick to her for the rest of her days. After leaving Saint Moritz, he would repeat the story of how he had met the notorious Ann Woodward whenever the opportunity presented itself, embellishing his tale and relishing each detail.

Ann Woodward eventually came to learn that Truman was constantly talking about her. She grew to despise the man she referred to as a “little toad,” but she also should have known he was dangerous. He once confessed, “I am about as tall as a shotgun, and just as nasty.” He was especially keen to hurt those who hurt him. An insult to his sexuality would sharpen his wit. In later years, Truman’s friend Lee Radziwill echoed Ann Woodward’s words when Truman Capote was in a spat with his novelist rival Gore Vidal. “What does it matter?” Radziwill told the reporter Liz Smith. “They are just a couple of fags.”

When Truman learned of that conversation and was asked about it during a televised interview, he smiled sardonically and said, “I’ll tell you something about fags, especially southern fags. We is mean. A southern fag is meaner than the meanest rattler…. We just can’t keep our mouth shut.”

In the years that followed their encounter in the restaurant in Saint Moritz, the lives of Ann Woodward and Truman Capote would occasionally converge. Ann would drift, a wan figure, on the outskirts of the social world that had once admitted her, however reluctantly. Truman, a literary bad boy who built on his early success and went on to write what he called the “nonfiction novel” In Cold Blood, became more and more of an ornamental fixture, gadfly, commentator, walker, and chronicler of the New York social world that centered on La Côte Basque and shunned Ann. Though one was the striking socialite whose life had gone wrong with the killing of her husband and the other was a small-town southern homosexual of literary brilliance, the two were not that different. Both had overcome hardscrabble, unsteady, fraught childhoods. Both had cajoled, clawed, and charmed their way into the elite circles they sought to enter. Both were vulnerable and mean. Both were familiar with violence. And the violence that caused the death of Billy Woodward would, as recounted by Truman Capote in 1975, incite fresh violence that would ultimately destroy them both. What began with insults in Saint Moritz would end in death for one and ignominy for the other.

About The Author

Roseanne Montillo is an accomplished research librarian who earned her MFA from Emerson College and has taught creative writing at Emerson and the Tufts Extension School. In addition to Deliberate Cruelty, she has published four previous works of narrative nonfiction to critical acclaim—Fire on the TrackThe Wilderness of RuinAtomic Women, and The Lady and Her Monsters

Why We Love It

“Murder, betrayal, secrets, and intertwined literary and social scandals set among the elite of literary and cafe society, this is true crime with a murderess wearing a designer evening gown and dripping in jewels.”

—Trish T., VP, Executive Editor, on Deliberate Cruelty

Product Details

  • Publisher: Atria Books (November 24, 2022)
  • Length: 320 pages
  • ISBN13: 9781982153731

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Raves and Reviews

"[A] sharp sliver of true crime...a vertiginous spiral of social death." --The New York Times

"It goes without saying that Deliberate Cruelty is awash in salacious material, but Montillo handles it with narrative skill — and deliberate fairness." --The Washington Post

"Deliberate Cruelty captures a multi-branched narrative of true crime and gossip and scandal, a literary history, noir mystery, and tragic denouement." --Daily Beast

"Deliberate Cruelty manages to be a hard-hitting true crime story and an interesting piece of cultural history, bringing out new facets of some well-known personalities to create a shocking story." --CrimeReads Most Anticipated Books of the Fall

“Montillo’s deeply researched exposé of the untimely downfall of glittering icons haunted by fundamental insecurities and entrenched demons is a dishy true-crime, literary critique mash-up.” --Booklist

"This engaging, well-researched book will appeal to true-crime aficionados, Capote fans, and anyone interested in a darkly intriguing story well told. A compelling mix of true crime and literary biography." --Kirkus Reviews

"The tragic collision of two lives — Truman Capote and socialite-murderess Ann Woodward — makes for riveting reading in Roseanne Montillo's memorable account of two social-climbing strivers and the lives they touched." —Meryl Gordon, author of Bunny Mellon and Mrs. Astor Regrets

"When the life of Ann Woodward, self-made socialite from Kansas, collided with that of Truman Capote, genius jester at the court of the beautiful people, the result was a twentieth century morality tale of enduring fascination, rooted in a particular kind of American dream - the one that seeks entry into the sleek, exigent world of Manhattan's Upper East Side. Roseanne Montillo tells the story supremely well, with a cool relentlessness reminiscent of Zola." —Laura Thompson, author of The Heiresses

"Brash and beautiful, Ann Woodward’s escape from a hardscrabble past and her ambitious rise from model and showgirl to the upper tiers of New York’s high society is a both a rags to riches story and a cautionary tale -- just the kind of story literary provocateur Truman Capote adored. In crafting the side-by-side tales of two arriviste strivers born of humble roots, Roseanne Montillo has given us a thrilling, tragic, Gatsby-esque saga. A wild romp of a story, boldly and beautifully told." —Neal Thompson, author of The First Kennedys and A Curious Man

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