A Woman Accidentally Killed Her Rich Husband In The ’50s. A New Book Uncovers What Came Next.

Deliberate Cruelty reframes a ’50s crime scandal as a story about ethics. The result is more moralistic than revealing.

On the night of Oct. 30, 1955, Ann Woodward shot her husband, William, in their lavish Long Island home. The banking fortune heir was dead by the time the police arrived at the North Shore estate, and Woodward, a former radio actor, cried as she confessed to officers that she’d confused him with an intruder.

Friends told police investigators that the couple, both expert hunters, had been talking about a rash of neighborhood break-ins at a dinner party that night. Weeks later, a burglar even admitted he’d been on the home’s roof and was scared off by the gunshot.

Woodward testified in front of a grand jury, and ultimately, no charges were brought against her. Still, the story took off in the press. The couple wasn’t just rich — they were society-page fixtures. He had been called the country’s most eligible bachelor; she was a club “showgirl” who, in the classist and gendered parlance of the time, had married “up” when she became Woodward’s wife. The story of the shooting was turned into a mystery about the marriage itself: Had she really not known it was her husband? Had it actually been an accident? Had he been trying to cut her out of the will?

Even decades after the story faded from headlines, it easily sparked dinner party debates. Truman Capote included a thinly disguised fictionalized portrait of Woodward in his 1986 novel, Answered Prayers. Vanity Fair scribe Dominick Dunne wrote The Two Mrs. Grenvilles, another fictionalized version of the story told from the perspective of the mother-in-law, which was adapted into a 1987 miniseries.

Now, Roseanne Montillo, a biographer of literary figures like Mary Shelley and the scientists behind the atomic bomb, sets out to reexamine the Woodward story. In Deliberate Cruelty: Truman Capote, the Millionaire's Wife, and the Murder of the Century, she grapples with Capote’s effects on Woodward through his novelization of her story.

Putting the two in conversation — the scandalous murder protagonist and the scandal-hungry journalist — is potentially interesting, especially as true crime ethics becomes an even more heated topic of debate. But the premise of the Capote–Woodward connection requires a bit of stretching; Montillo plays up the causes and consequences through speculation and collapses Capote’s narrator with Capote. Ultimately, the book’s intriguing conceit of historical nonfiction as an ethics lesson doesn’t fully cohere into the new perspective it promises.

Montillo’s skills as a historían are most evident when she focuses on Woodward, especially her backstory in Pittsburgh, Kansas.

She zeroes in on Woodward’s mother, Ethel Crowell, a transgressive figure who might have inspired her daughter’s ambition. Crowell got a sociology degree in the ’20s and became a teacher and high school principal at a time when married women weren’t allowed to teach. She was charismatic and passionate, gave lectures about Kansas history at her local church, divorced her husband, and started a taxi cab business in the midst of the Depression.

But she always struggled to make ends meet. Her daughter Ann, Montillo suggests, didn’t want to experience her independent mother’s difficulties. She took off for New York City as a model, then became a club showgirl, a radio actor, and the “most beautiful girl on radio” before she met William Woodward.

Deliberate Cruelty is told in Montillo’s omniscient voice, and her interpretations are presented as fact. This isn’t much of a problem in the expository chapters, but it becomes more limiting as the book moves into the more mysterious aspects of the Woodwards’ marriage from 1943.

For instance, she wheels out what seem to be unsubstantiated rumors that William, known as Billy, a racehorse enthusiast, was gay and that his father set up his first meeting with Ann. No sources are cited; how does she know this? Was it true or is this conjecture drawn from the kind of gossip that emerged only after the public became greedy for scandal after the shooting?

Depending on one’s tastes, the prose comes off either readably breezy or insipidly efficient, but there’s little dialogue, so the story never quite comes alive. Take Montillo’s description of that meeting: “She knew very well the power she had over men, and she knew how to use it.” Bill looked at “her breasts spilling out from a bra that was too small, and at her legs in those black stockings that drove men wild.”

None of the quotes or descriptions are tied to citations, and it’s very difficult to discern what’s fact and what’s novelization. The book is based on press accounts and police reports, but they’re just rehashed, rather than analyzed or questioned.

Just like the couple’s contemporaries, the book plays up that the marriage was in crisis. The household staff witnessed violent squabbles that are painted as mutually abusive, as if both had equal power: “Ann flung bottles, shoes, ashtrays at Billy, and Billy retaliated by slapping her face,” Montillo writes. After they had two children, Billy became abusive and asked for a divorce by 1948. Montillo suggests Ann had started losing power over her husband because her bedroom “tricks began to seem dated, as he met and became involved with younger people who were even more interesting to him than a former chorus girl from Kansas.”

The story often feels more like retrospective projection onto historical caricatures rather than a true reconsideration making new connections that build up to an original narrative. A more probing revisitation might grapple more explicitly with the ways the speculation about Ann might have been classist and misogynist, propounded first within the couple’s circles and then in the press.

Instead, Montillo relies on her critique of the cruelty of Capote’s novel.

By the ’70s, Capote was hungry for content after the massive success of In Cold Blood. According to Montillo, before he went off to Kansas to investigate the murder of the Clutter family for his 1966 bestseller, he had originally wanted to write about the Woodward story, intrigued by headlines like “Showgirl Wife Kills Heir with Shotgun Blast.”

Montillo shows how Capote, like Woodward, grew up with an ambitious mother who dumped her first husband, remarried, and reinvented herself. And Woodward was like a real-life version of Capote’s Breakfast at Tiffany’s protagonist Holly Golightly, desperately trying to leave her past behind.

By then, Capote had outgrown his role as the gay pet of high-society women like Babe Paley and Lee Radziwill and wanted to show that there was nothing to envy about the upper classes. Answered Prayers, his last work — unfinished, and only published posthumously — was supposedly meant to be a critique of that echelon’s mores, narrated by a bisexual hustler, P.B. Jones.

In the first published excerpt, Jones meets Lady Ina Coolbirth (later speculated to be based on Paley), who gets drunk and tells him all about Ann Hopkins (widely speculated to be based on Woodward). In Coolbirth’s telling, Hopkins was a ''jazzy little carrot-top killer'' who ''looked rather like a malicious Betty Grable'' and was known to men in the French Riviera as ''Madame Marmalade'' for an oral trick performed with jam. She’d killed her husband on purpose because otherwise she’d be left with nothing in a forthcoming divorce.

Arguably, this novelistic portrait was actually a critique of that kind of slut-shaming, but Montillo doesn’t raise that possibility. Instead, she plays up how much Capote supposedly and purposefully meant to hurt Woodward through the portrait. She recreates a scene between Capote and Woodward — again, based on the notoriously fabulistic Capote’s telling — where she supposedly called him an anti-gay slur and he called her “Mrs. Bang Bang.”

She implies that he just spent years waiting for a way to get back at her, and the opportunity came with Answered Prayers. “It’s possible that Truman Capote loathed the socialite Ann Woodward because she reminded him so much of his mother,” she writes. “But he may also have been so cruel to her because Ann Woodward seemed too much like him as well.”

The speculation extends to Woodward’s death by suicide three days before an excerpt of the novel was due to be published in Esquire. Montillo presents no evidence that Woodward knew that the particular excerpt would focus on her. It’s not that one doubts that a revival of a scandal could have been the last straw for a woman who had been supposedly expelled from her former social circle and was trying to put her past behind her. But no suicide note was found.

In some ways, Deliberate Cruelty highlights the problem with meta true crime.

It also seems likely that Woodward had been experiencing feelings of isolation from her former friends and stress about her younger son, Jimmy, who attempted suicide before she did. The Woodward family would continue to experience mental health struggles. A year after her own death, Jimmy died by suicide. In 1999, William, her older son, also killed himself.

William’s friends “blamed his depression, and in no small part, a family history,” Montillo writes. “They could also have blamed Truman Capote.” It seems a lot to put on the back of one person’s fictional output. Arguably, social misogyny and classism were also responsible.

In some ways, Deliberate Cruelty highlights the problem with meta true crime. People are often drawn to crime stories because murder mysteries provide voyeuristic glimpses into marriages and allow us to endlessly interpret motivations. But to repeat the lore about Woodward without addressing the gendered dynamics at play is to miss a huge piece of the puzzle.

In recent years, Amanda Knox, exonerated of a 2007 crime that made her infamous, has repeatedly critiqued the media’s framing of her story. Knox said the media mixed fact and gendered speculation to depict her as a “dirty man-eater.” She might as well have been talking about Montillo’s portrait of Woodward. ●

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