F rom his first day in office in 1930, Harry Anslinger had a problem, and everybody knew it. He had just been appointed head of the Federal Bureau of Narcotics—a tiny agency, buried in the gray bowels of the Treasury Department in Washington, D.C.—and it seemed to be on the brink of being abolished. This was the old Department of Prohibition, but prohibition had been abolished and his men needed a new role, fast. As he looked over his new staff—just a few years before his pursuit of Billie Holiday began—he saw a sunken army who had spent fourteen years waging war on alcohol only to see alcohol win, and win big. These men were notoriously corrupt and crooked—but now Harry was supposed to whip them into a force capable of wiping drugs from the United States forever.

Harry believed he could. He believed that the response to being dealt a weak hand should always be to dramatically raise the stakes. He pledged to eradicate all drugs, everywhere—and within thirty years, he succeeded in turning this crumbling department with these disheartened men into the headquarters for a global war that would continue for decades. He could do it because he was a bureaucratic genius—but, even more crucially, because there was a deep strain in American culture that was waiting for a man like him, with a sure and certain answer to their questions about chemicals.

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Jazz was the opposite of everything Harry Anslinger believed in. It is improvised, relaxed, free-form. It follows its own rhythm. Worst of all, it is a mongrel music made up of European, Caribbean and African echoes, all mating on American shores. To Anslinger, this was musical anarchy and evidence of a recurrence of the primitive impulses that lurk in black people, waiting to emerge. “It sounded,” his internal memos said, “like the jungles in the dead of night.” Another memo warned that “unbelievably ancient indecent rites of the East Indies are resurrected” in this black man’s music. The lives of the jazzmen, he said, “reek of filth.”

His agents reported back to him that “many among the jazzmen think they are playing magnificently when under the influence of marihuana but they are actually becoming hopelessly confused and playing horribly.”

The Bureau believed that marijuana slowed down your perception of time dramatically, and this was why jazz music sounded so freakish—the musicians were literally living at a different, inhuman rhythm. “Music hath charms,” their memos say, “but not this music.” Indeed, Anslinger took jazz as yet more proof that marijuana drives people insane. For example, the song “That Funny Reefer Man” contains the line “Any time he gets a notion, he can walk across the ocean.” Anslinger’s agents warned that’s exactly what drug users were like: “He does think that.”

Anslinger looked out over a scene filled with rebels like Charlie Parker, Louis Armstrong and Thelonious Monk, and—as the journalist Larry Sloman recorded—he longed to see them all behind bars. He wrote to all the agents he had sent to follow them and instructed: “Please prepare all cases in your jurisdiction involving musicians in violation of the marijuana laws. We will have a great national round-up arrest of all such persons on a single day. I will let you know what day.” His advice on drug raids to his men was always simple: “Shoot first.”

He reassured congressmen that his crackdown would affect not “the good musicians, but the jazz type.” But when Harry came for them, the jazz world would have one weapon that saved them: its absolute solidarity. Anslinger’s men could find almost no one among them who was willing to snitch, and whenever one of them was busted, they all chipped in to bail him out.

In the end, the Treasury Department told Anslinger he was wasting his time taking on a community that couldn’t be fractured, so he scaled down his focus until it settled like a laser on a single target—perhaps the greatest female jazz vocalist there ever was.

He wanted to bring the full thump of the federal government down upon that scourge of modern society, his Public Enemy #1: Billie Holiday.

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One night, in 1939, Billie Holiday stood on stage in New York City and sang a song that was unlike anything anyone had heard before. ‘Strange Fruit’ was a musical lament against lynching. It imagined black bodies hanging from trees as a dark fruit native to the South. Here was a black woman, before a mixed audience, grieving for the racist murders in the United States. Immediately after, Billie Holiday received her first threat from the Federal Bureau of Narcotics.

Harry had heard whispers that she was using heroin, and—after she flatly refused to be silent about racism—he assigned an agent named Jimmy Fletcher to track her every move. Harry hated to hire black agents, but if he sent white guys into Harlem and Baltimore, they stood out straight away. Jimmy Fletcher was the answer. His job was to bust his own people, but Anslinger was insistent that no black man in his Bureau could ever become a white man’s boss. Jimmy was allowed through the door at the Bureau, but never up the stairs. He was and would remain an “archive man”—a street agent whose job was to figure out who was selling, who was supplying and who should be busted. He would carry large amounts of drugs with him, and he was allowed to deal drugs himself so he could gain the confidence of the people he was secretly plotting to arrest.

Many agents in this position would shoot heroin with their clients, to “prove” they weren’t cops. We don’t know whether Jimmy joined in, but we do know he had no pity for addicts: “I never knew a victim,” he said. “You victimize yourself by becoming a junkie.”

He first saw Billie in her brother-in-law’s apartment, where she was drinking enough booze to stun a horse and hoovering up vast quantities of cocaine. The next time he saw her, it was in a brothel in Harlem, doing exactly the same. Billie’s greatest talent, after singing, was swearing—if she called you a “motherfucker,” it was a great compliment. We don’t know the first time Billie called Jimmy a motherfucker, but she soon spotted this man who was hanging around, watching her, and she grew to like him.

When Jimmy was sent to raid her, he knocked at the door pretending he had a telegram to deliver. Her biographers Julia Blackburn and Donald Clark studied the only remaining interview with Jimmy Fletcher—now lost by the archives handling it—and they wrote about what he remembered in detail.