How the Government Targeted “Strange Fruit” Singer Billie Holiday with Drug Arrests

In 1939, Billie Holiday rode the service elevator in a midtown Manhattan hotel on her way to sing on stage. Of course, the hotel had a front door, but Holiday wasn’t allowed to use it because she was Black. Little did she know this was just the beginning of the troubles that would follow her that night.

Holiday stuck to her setlist, including singing “Strange Fruit,” a hauntingly emotional song against lynching with lyrics like “Southern trees bear strange fruit / Blood on the leaves and blood at the root / Black bodies swinging in the southern breeze / Strange fruit hanging from the poplar trees.” Her self-described way of being able to “sing like an instrument” made the performance particularly effective.

But that night she received a warning from the Federal Bureau of Narcotics (FBN), a government agency which lasted from 1930 to 1968: She was never to sing the song again. The link between the song and the anti-drug agency may feel disjointed, except that FBN commissioner Harry Anslinger drew a direct correlation.

“To Harry Anslinger, Billie Holiday was like the symbol of everything that America had to be afraid of,” Johann Hari, who wrote the book Chasing the Scream: The First and Last Days of the War on Drugs, told WNYC. “She had a heroin addiction because she’d been chronically raped as a child and she was trying to deal with the grief and the pain of that. And also, she was resisting white supremacy. And when she insisted on continuing on her right as an American citizen to sing ‘Strange Fruit,’ Anslinger resolves to destroy her.”

Anslinger was widely known as an “extreme racist in the 1920s”

When Anslinger first took on the role in the new agency that was part of the Treasury Department, he was determined to “eradicate all drugs, everywhere.” He had previously been part of the Department of Prohibition, but since the prohibition had been abolished, he was more determined than ever to take a strict stance on drugs.

Among his strategies was his belief that jazz music was a part of the problem. “It sounded like the jungles in the dead of night,” a memo he wrote said, while another said “unbelievably ancient indecent rites of the East Indies are resurrected” and that the songs “reek of filth.” His agents even reported back to him that “many among the jazzmen think they are playing magnificently when under the influence of marijuana, but they are actually becoming hopelessly confused and playing horribly.”

The reason for his targeting of a genre of music came down to his widely-known bias. “You have to understand that he was regarded as an extreme racist in the 1920s,” Hari told WNYC. “He used the N word so often in official memos that his own senators said he should have to resign.”

So the controversial nature of “Strange Fruit” among the musicscape at the time gave him the excuse he needed to go after Holiday. “This was not a time when there were political pop songs,” Hari said. “And to have an African American woman standing in front of a white audience singing a song against white supremacy and its violence was viscerally shocking at that moment.” Coupled with Holiday’s known struggles with alcohol and drug addiction over the years, Anslinger became laser-focused on taking Holiday down.

Anslinger sent undercover agents after Holiday

Despite the fact Anslinger didn’t like hiring Black agents, he assigned Jimmy Fletcher to investigate Holiday since she was based in Harlem and he wanted his agent to be able to blend in. Fletcher himself believed, “You victimize yourself by becoming a junkie,” so he seemed like the right fit for the job.

Fletcher soon frequented Holiday’s neighborhood and saw her drinking and doing cocaine first-hand, but Holiday noticed him around too and grew to like him. Although Fletcher did eventually have to raid her, they grew close and were even seen dancing together at Club Ebony.

“I had so many close conversations with her, about so many things,” Fletcher later said, according to Hari, who said the agent fell in love with Holiday. “She was the type who would make anyone sympathetic because she was the loving type.”

Holiday’s husband worked with the FBN to set her up

Around the time, Holiday would often show up to her performances beaten by her husband, Louis McKay, so she eventually cut him off. He was so enraged, even being quoted as saying, “I got enough to finish her off,” Mari wrote in Politico. McKay went down to Washington, D.C., met with Anslinger and they decided that McKay would set Holiday up.

Holiday was caught and put on trial. “It was called The United States of America versus Billie Holiday—and that’s just the way it felt,” Holiday wrote in her autobiography. Despite telling the judge that she simply wanted the opportunity to recover and find “the cure,” she was sentenced to a year in prison in West Virginia—where she had to kick her habit but also didn’t sing a note.

When she was released from Alderson Federal Prison in 1947, her license to perform at her cabarets was revoked. But that didn’t seem to faze her. Shortly thereafter, she played a sold-out show at Carnegie Hall, a venue she went on to perform at more than 22 times.

Even after reportedly being framed, Holiday continued to perform “Strange Fruit”

Anslinger wasn’t done with Holiday. He recruited Col. George White, who was a “sensation as the first and only white man ever to infiltrate a Chinese drug gang, and he even learned to speak in Mandarin so he could chant their oaths with them.” At a time when Holiday claimed she had been clean for more than a year, White busted Holiday at San Francisco’s Mark Twain Hotel, saying he found opium in a wastebasket and a heroin kit in the room.

“It’s pretty clear, I think, from reading the historical documents, that [White] planted drugs on Billie Holiday that night,” Hari said. “She’s broken and destroyed again. She’s really back on the path of addiction.”

This time, things didn’t quite bounce back. She’d go through remission, only to be addicted once again—and her career spiraled along with it. But she kept performing throughout the 1950s, and most importantly, she kept singing “Strange Fruit.” “The kind of courage not only that she would risk her career and her career mobility but that she actually risked her life and her freedom because she felt that she had to sing this song,” Farah Jasmine Griffin of Columbia University’s African American and African Diaspora Studies told NPR.

Anslinger continued to pursue Holiday in the hospital

One day in 1959, Holiday collapsed and was sent to the hospital—and she feared Anslinger wasn’t done with her yet, even after she was diagnosed with liver disease. “So she’s very ill, and she goes into heroin withdrawal because she’s not given any in the hospital,” Hari said. “And Maely Dufty, her friend, managed to insist that she was given methadone, and she began to recover. Obviously, heroin withdrawal is very dangerous if you’re extremely physically weak, as she was.”

And then Holiday’s worry came true: Anslinger’s team arrested her on her hospital bed.

“It sort of was like the last straw that the public or the system could do to her, and I think that that really took the heart out of her,” Holiday’s friend Alice Vrbsky said. It became clear what was happening, and protests were even held outside the hospital as people carried signs saying, “Let Lady Day Live!” referring to her by her nickname.

But after 10 days, the methadone was cut off on Anslinger’s instruction. “She was in very bad shape,” Vrbsky added. “I could see on her face and in her whole condition that she wasn’t well.” On July 17, 1959, Holiday died.

Anslinger reportedly was satisfied, writing, “For her, there would be no more ‘Good Morning Heartache,’” Hari wrote.

He had succeeded in his decades-long pursuit to take down Holiday, a task fueled by his own racist views (case in point: he addressed Judy Garland’s drug addiction by telling her to take longer vacations). In September 1962, Anslinger was even honored by President John F. Kennedy for his work on the war on drugs.

While Holiday unfairly met her end, her legacy and determination transcend today. “We’re at the point now where we applaud anything. Like, oh, such and such person took a stance,” Griffin said. “They aren’t going to get the hit that Billie Holiday got. They aren’t going to go to prison because they sang a song, right? So I think it’s important to remember that she did that when the cost and the consequences were much, much harsher.”