Tragic Details About Billie Holiday

Billie Holiday, nicknamed "Lady Day," is well-known for her legacy as a jazz legend, but the remainder of her life is shrouded in mystery.

Two popular movies—Lady Sings the Blues (1972) and The United States vs. Billie Holiday (2021)—have endeavored to tell the story of Holiday beyond the music. But even these biopics cannot necessarily be taken as fact. While the former film was based upon Holiday's own 1956 autobiography, Lady Sings the Blues, even her own account of her life contains inconsistencies and has been partly disputed.

Even so, through the reporting of the time and the accounts of people who were a part of Holiday's life, her story can be pieced together. The pieces may not add up to the complete picture, but they reveal elements of tragedy, FBI-targeting, and failures on the part of the people around the singer. But while these accounts detail some of Holiday's hardships, such as addiction and related arrests, they do not do justice to her unforgettable work as a civil rights activist. Thankfully, while tragedy shadowed Holiday's life, it has not defined her legacy.

Her childhood was darkened by poverty, an absent father, and abuse

Billie Holiday was born Eleanora Fagan on April 7, 1915, to teenage parents Sarah Julia "Sadie" Fagan and Clarence Holiday (via Biography). According to Sunday Post, Clarence abandoned her and her mother shortly after she was born. Her mother was often traveling for work on long-distance trains, so Billie spent most of her time with relatives, some of whom were abusive.

In her book, Lady Sings the Blues, Billie recalled having to share a bed with her cousin Ida's two young children, Henry and Elsie. Henry wet the bed every night, and Ida would accuse Billie and beat her. "When she was upset she'd beat me something awful... with her fists or a whip," Holiday wrote. "One time she heard me say 'Damn it' and she thought this was so sinful she tossed a pot of hot starch at me. She missed, though, because I ducked." When Billie suggested that she and Elsie sleep on the floor one night to prove it was Henry wetting the bed, Ida beat her again for "being smart with her."

According to a 1939 interview with Downbeat magazine, Holiday revealed that she and her mother struggled while living on 145th Street near Seventh Avenue in Manhattan. "Mother and I were starving," she told the magazine. "It was cold. Father had left us and remarried when I was 10. Mother was a housemaid and couldn't find work. I tried scrubbing floors, too, but I just couldn't do it."

At 10, she experienced 'the worst thing that can happen to a woman'

When Billie Holiday was 10 years old, one of her neighbors turned up at her apartment and told her that her mother had sent him. According to the Toronto Star, the man was a 40-something-year-old named Wilbert Rich. He took Holiday to a house under the false premise that she would be waiting there, at her mother's request, until her mother came to pick her up. Her mother didn't come, and it grew dark outside, so the sleepy Holiday lay down on a bed at Rich's suggestion. As soon as she did, Rich "pinned her down and raped her." A woman who had let them into the house tried to hold Holiday's head and arms down. Holiday put up a fight, screaming and clawing at her attackers, and before long, police officers — accompanied by Holiday's mother — broke the door down.

In Lady Sings the Blues, Holiday wrote that, after the attack, the cops at the precinct "treated [her] like [she'd] killed somebody." They accused Holiday of seducing and coercing Rich, and as her mother "cried and screamed and pleaded," the officers locked Holiday in a jail cell for two days.

"It's the worst thing that can happen to a woman," Holiday wrote of the attack in her autobiography. "And here it was happening to me when I was ten."

She was sent to a Catholic reform school that doled out horrific punishments

After she was sexually assaulted by her neighbor, Billie Holiday was sent to a Catholic reform school for a year as punishment. According to, The House of the Good Shepherd was a "school known for meting out harsh punishments for even minor transgressions."

In Lady Sings the Blues, Holiday wrote about the harsh punishments the nuns would mete out. One Easter, her mother came to visit and gave her an Easter basket full of boiled eggs and fried chicken. Holiday was being punished at the time, so the nuns made Holiday watch as the other girls feasted on the food. That night, they locked her in a room with the body of another girl from the school who had died. "I couldn't sleep," Holiday recalled. "I couldn't stand it. I screamed and banged on the door so, I kept the whole joint from sleeping. I hammered on the door until my hands were bloody."

'Strange Fruit' was a painful song for Billie Holiday to sing

"Southern trees bear a strange fruit, Blood on the leaves and blood at the root, Black body swinging in the Southern breeze, Strange fruit hanging from the poplar trees..."

So goes Billie Holiday's haunting, best-selling song, "Strange Fruit." According to Biography, the song was written and composed by a Jewish activist named Abel Meeropol after he saw a photograph of two lynched men in Indiana. He showed the song to a nightclub owner, who showed it to Holiday, who was "deeply moved" by it. The song reminded the singer of her father, Clarence Holiday, who died of lung cancer after he was turned away from a hospital for being Black. "It still depresses me every time I sing it," she wrote in Lady Sings the Blues. "It reminds me of how Pop died. But I have to keep singing it, not only because people ask for it, but because 20 years after Pop died, the things that killed him are still happening in the South."

"Strange Fruit" received mixed responses from white audiences. Immediately following her first performance of the song in 1939, she received her first threat from the Federal Bureau of Narcotics. The song reportedly led the bureau's racist commissioner, Harry Anslinger, to become fixated on causing Holiday's downfall.

The FBI worked to ensnare Billie Holiday for her heroin addiction

Billie Holiday married addict and drug dealer Jimmy Monroe in 1941, according to JazzWise. Holiday already used alcohol and marijuana heavily, but she began getting high on opium. A couple of years later, due to the opium shortage during World War II, she began using heroin intermittently before giving into a full-blown addiction. She began spending most of the money she made on fueling her habit.

Federal Bureau of Narcotics Commissioner Harry Anslinger was determined to silence Holiday, so he hired a Black street agent named Jimmy Fletcher to keep an eye on her. According to Politico, Fletcher infiltrated the drug community from within; he was allowed to sell drugs himself to build trust. Before long, Holiday "grew to like him," and he fell in love with her. Even so, he eventually set her drug bust in motion by pretending to be delivering a telegram. When a policewoman was sent over to search Holiday for drugs, Holiday insisted on stripping herself  —and then peed on the floor in front of the officers.

The FBI's targeting of Billie Holiday led to her arrest and notorious trial

Billie Holiday and fellow jazz icon Louis Armstrong both used drugs and had a shared manager, Joe Glaser. To protect Armstrong from getting busted for drug possession, Glaser worked with officials to get Holiday busted. The Los Angeles Times reports that the raid occurred in May 1947 at a nightclub in Philadelphia. Holiday's arrest led to a highly publicized trial in the U.S. District Court. "It was called 'The United States of America versus Billie Holiday,'" she wrote in Lady Sings the Blues (via Politico), "and that's just the way it felt."

Holiday told the judge that she wanted to go to a hospital to get clean. "I want the cure," she said (via Politico). Instead, she was sentenced to a year in prison. According to JazzWise, Holiday was forced to get clean — cold turkey — while doing time at the Alderson Federal Prison Camp in West Virginia. "[Billie] paid her debt to society," her friend wrote later (via Politico), "but society never paid its debt to her."

Her 'cabaret card' license in New York state was revoked

As noted in the BBC documentary Reputations: Billie Holiday, the singer "refused to sing a note" during her entire almost-10 months in prison. According to, Holiday attended church every Sunday while doing her time, and her supervisor reportedly described her as "generous, quiet, lady-like, [and] matter-of-fact." She was released from prison a couple of months early, in March 1948, due to "good behavior," per Slate.

Holiday's cabaret card had been revoked when she was arrested, which meant she could no longer play at nightclubs that had liquor licenses, according to Even after she served her time, the police refused to reinstate her card for more than a decade. Nightclub shows had previously been a solid stream of income for Holiday, and she found herself with a dangerous amount of free time without them. Still, she began to set her comeback in motion by playing a winning, sold-out, headline show at Carnegie Hall, which prompted six encores.

The men in her life failed her, putting her career, her health, and her reputation on the line

Despite her lack of cabaret card, Billie Holiday got a hookup to perform at New York City's Ebony Lounge through its owner — and her new boyfriend — John Levy, according to Slate. Still, due to her newfound free time — and the influence of her first husband, Jimmy Monroe — Holiday fell back into her heroin habit just a few months after her release from prison. "There isn't a soul on this earth who can say for sure that their fight with dope is over," Holiday once said (via, "until they're dead."

Levy soon began to abuse, manipulate, and short-change Holiday, not paying her sufficiently for her shows at the Ebony Lounge, per Slate. He was also allegedly a police informant, and in January 1947, he cooperated with federal narcotics agents and planted drugs on her (though they both appeared in reports of the arrest).

According to Hettie Jones' Big Star Fallin' Mama, Holiday managed to prove her innocence with the help of friends, a good lawyer, and a lot of money. She started playing at nightclubs outside of New York City, calling herself a DP—a name for World War II refugees, which means "displaced person."

She was arrested on narcotics charges on her deathbed

Billie Holiday made her last public appearance on May 25, 1959. According to, she had to be helped off the stage after performing a single song, "T'Aint Nobody's Business If I Do." She had also quickly lost a whopping 50 pounds by that time, according to The Sun.

After collapsing at her apartment six days after the performance, she was admitted to the New York Metropolitan Hospital and diagnosed with cirrhosis of the liver. While she was there, federal narcotics officers raided her Harlem apartment and claimed to have found heroin. The federal agents pressed charges against her and stationed armed guards outside of her hospital room. She died "of pulmonary edema and heart failure caused by cirrhosis of the liver on July 17, 1959, at the age of 44" (via The Sun). When she breathed her final breath, federal narcotics officers were still stationed outside of her room.