Truman Capote, a Cyanide Pill, and a Shocking High Society Murder

HBO show The Gilded Age is an entertaining romp of extravagant houses, decadent gowns, and deliciously catty behavior. It’s fun to watch, but there’s something about it that feels too high gloss, not quite real. It’s Hollywood’s interpretation of New York high society in the late 19th century—magnified, zhuched up, and distilled to only the best lines.

That’s what I thought, at least, until I began to research what Life Magazine called “the shooting of the century.” The gowns may have gotten a little less voluptuous and a little more scandalous (Agnes van Rhijn would be horrified by the amount of leg shown), the transportation added a whole new level of “horse” power, and the world of the famously rich had become ever so slightly bigger and more connected, but the behavior of America’s highest social class in the 1950s—well, that remained snobby and scandalous.

The year was 1955 and the characters in this story are 40-year-old Ann Woodward, a woman of dubious origin (read: low class who once performed on—gasp—the stage) and the affluent man she “ensnared” into marriage against his family’s wishes, the 35-year-old Billy Woodward. On the night of October 30, the police were called to an emergency in a tony neighborhood of Oyster Bay, Long Island. When they busted into the mansion, they found Ann on the ground, shotgun nearby, cradling the body of her naked and dead husband.

For the rest of her life, Ann would be dogged by one question: did she commit murder or had she been a victim in a tragic accident? From the New York courts to drawing room gossip and the pages of books by two of the biggest literary figures of the day—Truman Capote and Dominick Dunne—everyone was talking about what happened the night Ann Woodward killed her husband.

“Once upon a time, a jazzy little carrot-top killer rolled into town”

During his life, Billy was popular in the way that all well-to-do men who conform to the privileged path prescribed for them are. He went to all the best schools—Buckley, Groton, then Harvard—then joined the U.S. Navy to fight in WWII, for which he earned a Purple Heart. After upholding his family name in battle, he came home and accepted a respectable job at the bank his father ran, excelled in the family hobby-cum-business of horse breeding, and joined all the finest clubs in the area.

But while he may have been popular among his set, the papers professed shock at the crowd who turned out for his funeral. According to LIFE’s 1955 account, one police officer on the scene said it was “the biggest funeral since Babe Ruth’s.” The author of the piece professed particular astonishment at the number of “help” from around the city who turned out to pay their respects.

In true Gilded Age fashion, writer Cleveland Amory felt the need to add an editorial comment to his account of the funeral, writing “This too was fitting. Help as a class is the most snobbish of all groups when it comes to people ‘of good family,’ although they haven’t the slightest idea what the phrase means.”

(Let’s pause here for just a moment to revel in the flood of arrogance and condescension from a distinguished man of letters born to a powerful Boston family writing in one of the country’s leading midcentury newsmagazines.)

The one person who was not in attendance at the funeral that day was Ann Woodward. She sent her two young sons to say goodbye to their father with their grandmother (paternal, of course), while she remained removed and silent.

Most of the people whose voices were heard in the aftermath of the tragedy were either born into the upper crust or had clawed their way into it and weren’t about to show any sign of weakness towards Ann and risk giving up their newfound position or haughty attitude. So, needless to say, there aren’t many rousing defenses or positive portrayals of Mrs. Woodward.

What is known is that she rose from rags-to-society riches through sheer talent, will, and good looks. Ann pulled herself out of poverty in Kansas to become a leading model and radio actress for a time. Her obituary in The New York Times says she became known as “the most beautiful girl on the radio,” a line that wasn’t a slight like today’s infamous saying, “You have a face for radio.”

Capote would later distill Ann’s arrival to New York and class rise into this opening gut punch of a line: “Once upon a time, a jazzy little carrot-top killer rolled into town.”

The origins of Ann and Billy’s relationship are shrouded in gossip. One version of events has it that Billy’s father, William Woodward, Sr., met Ann first, and possibly had an affair with her while she was working as a showgirl. Through this association, although presumably without knowledge of the exact nature of the relationship, Billy met and became entranced by Ann.

What is known is that the two were married in 1943. While they would go on to have two sons, by all accounts the volatile relationship showed cracks early on. From nearly the words “I do,” their relationship was characterized by copious amounts of alcohol, drugs, and sex—and not only with each other.

According to Susan Braudy, who wrote about the scandal in This Crazy Thing Called Love, the disconnect at the core of their relationship might have been that they weren’t on the same page about the role Ann would play. Braudy suggests that Billy might have married this wholly unsuitable woman as a breath of fresh air, expecting her to help him get out from under the thumb of his parents. But Ann was interested in gaining entry into his social class. When she became Mrs. William Woodward, Jr., she set about conforming to the social rules and doing everything she could to be accepted. (A real Bertha Russell, if you will.)

Alas, it was a doomed endeavor. “Ann’s nemesis was her mother-in-law, Elsie Woodward, who decreed that her daughter-in-law lacked style—and that meant class,” Braudy wrote in New York Magazine in 1992. Elsie, who excelled at zingers that could slice like a knife and who believed “money is more important than good health,” was not shy about her distaste. She allegedly once said, “I wish Billy had just married one of our attractive housemaids. At least we would have known where she came from.”

While both Billy and Ann were having affairs—allegedly many—it was mostly Billy’s escapades that were whispered about during his life. It was this fact that many would use as the basis for speculating about Ann’s guilt. In a complete lack of imagination, high society glommed on to the most tired trope of them all: philandering husband offed by scorned and jealous wife who claimed it was all a terrible accident.

But Braudy, for one, thinks Ann really was innocent and her argument is persuasive. Her investigation began after she happened to befriend one of the pair’s sons in the early 1970s and heard about the family history. (She unexpectedly met Ann once and recalled: “As Ann Woodward glanced at my bare knees, I realized that I was dressed improperly—and it mattered. It took me years to understand that Ann was treating me in the Woodward manner. This was the way her husband’s family had treated her.”)

Braudy said that Ann shooting her husband out of spite or because he threatened divorce made no sense. By that point, Ann was obsessed with holding onto her wealth and status. She would have gained a lot more money in a divorce than she did after his death, not to mention she became a social pariah and outcast even after a grand jury cleared her of wrongdoing.

Either way, our story comes to its crescendo on the night of October 30, 1955. That evening, Ann and Billy got dressed to the nines and went to a neighbor’s home, where there was a dinner being given in honor of the Duchess of Windsor.

When they returned to their home, no doubt boozed up, the couple made a fateful decision. There had been reports of several break-ins throughout their fashionable neighborhood. So when they repaired to their separate bedrooms for the night, they each decided to sleep with a loaded shotgun. According to Ann’s testimony, she woke up in the middle of the night to see a shadow looming in her doorway. She immediately fired her gun at what she thought was a burglar.

But it wasn’t. Ann had shot and killed her husband Billy while her two young sons slept nearby.

The fallout was swift. Tongues immediately started wagging, the well-attended funeral was planned, and a grand jury was swiftly convened. While she was acquitted of any wrongdoing in the eyes of the law not even a month after her husband’s death, Ann was forever tainted in the eyes of society. (While she was convinced of her daughter-in-law’s guilt, Elsie supported Ann’s acquittal. What would the people think if there was a convicted murderer in the family, after all?!)

Ann’s downfall was swift and after two decades she largely had fallen out of the spotlight. The gossip had finally died down. But then Truman Capote happened.

In 1975, Truman Capote announced that he was writing a new book. He told People magazine that this book would be like a gun: “There’s the handle, the trigger, the barrel, and, finally, the bullet. And when that bullet is fired from the gun, it’s going to come out with a speed and power like you’ve never seen—wham!”

While it was a novel, it quickly became clear that Capote planned to expose the secrets of all his high-society swans, masked by only the thinest of fictional veneers.

While the book would famously remain unfinished, an excerpt of it was published in the November issue of Esquire. The story, “La Côte Basque,” went into gory detail about call girl “Ann Cutler” who transformed herself into a society lady when she marries the well-to-do young “David Hopkins.” The couple had a volatile marriage, but it was Ann’s exploits that caused a sensation and earned her the “reputation up and down the French Riviera for what she did to men’s organs with her mouth and some marmalade.”

Finally, according to Capote’s tale, David discovered Ann had committed bigamy and was still married to a fellow back in Kansas. He had also fallen in love with a distant cousin, the right sort of girl, by this time. When Ann discovered his plans to end their relationship, she planned his murder and called it a case of mistaken identity.

No one—no one!—had any doubt as to who the story was about.

Just days before it was published, Ann was found dead in her Upper East Side appointment. She had taken a cyanide pill. Many believe that she had seen an advanced copy of the story, and that it was the last straw. Her mother-in-law was one of those.

Elsie tied up the affair in a fashion that only she could manage. After hearing the news of Ann’s death, she said, “Well, that’s that. She shot my son, and Truman just murdered her, and so now I suppose we don’t have to worry about that anymore.”