How Billie Holiday Broke Her Lawyer’s Heart

Lawyers have a position of responsibility when it comes to their clients, the courts and the community. They hear from people at some of the most difficult, emotional, and important times in their lives. They often hear the full story, much of which is not relevant for the purposes of court.

Celebrity criminal lawyer, Jake Ehrlich, heard a great deal about the life of his client, Billie Holiday, from her own mouth. He decided to publish a book about after her tragic death in 1959.

Holiday was once one of the world’s finest jazz singers, but died poor, alone, and under arrest in her New York hospital bed for the possession of narcotics, aged just 44.

Ehrlich represented Holiday when she was at the dizzying height of her career, successfully submitting to a jury that she had been framed for the possession of opium. Ehrlich says he knew, even then, that Holiday was a victim of drugs and society’s failed methods of dealing with users.

He recounts parts of the trial in his book, The Lost Art of Cross-Examination, and laments the senseless loss of Holiday, expressing his view that we have not yet reached the point of enlightenment where we want to help drug addicts the same way we care for people who are sick or injured.

Ehrlich’s story gives an insight into a criminal defence lawyer’s perspective when representing a client through a trial. He says Holiday, although incredibly gifted, was “not sharp”. Living up to the name her fans gave her—Lady Day—she was kind, completely trusting, and spent her money as though it would never run out.

She had recently completed a rehabilitation program for heroin addiction and was not using drugs when she arrived in San Francisco, where she was later framed and arrested. Ehrlich said:

“During her stay at the reformatory, no real attempt was made to get at the reason for her use of narcotics, so there was no real reason to believe that dope was through with her.”

Instead of being dependent on drugs at the time of her arrest, Holiday was entirely dependent on her lover and manager, John Levy, who controlled 100% of her earnings.

Ehrlich describes the circumstances of her arrest as “interesting and significant”:

“John Levy and Billie were relaxing in pyjamas in their hotel suite when the telephone rang. She took the call. It was for Levy. He took the receiver and exchanged a few monosyllables with the person on the other end of the line. Later he claimed that someone had asked for a business appointment and he had agreed to it.

He put down the telephone receiver and handed Billie a small package and told her to flush the contents down the toilet. As she neared the bathroom, there was a sharp rap on the door. Levy, who ostensibly had some personal reason for wanting the package to pass from immediate existence, nevertheless took the promptest action to open the door to the hallway, and in rushed Colonel George White with two San Francisco police inspectors and several of his agents from the Federal Bureau of Narcotics.”

Holiday was caught flushing a pipe containing opium down the toilet. Ehrlich says Colonel White placed the blame squarely on Holiday and hardly came after Levy at all. He writes that this was what tipped him off to the fact Levy and White were partners in an attempt to put Holiday in prison.

“I had before me a dual problem: (1) to defend my client against an apparently ironclad case for the prosecution, and (2) to unframe a frame-up.”

He said his greatest difficulty was Holiday’s enduring love for Levy. She suspected he had sinister intentions but firmly and irrationally decided she loved him anyway.

When Holiday was granted bail, she returned to singing nightly shows to packed venues. Word on the street, Ehrlich discovered, was that Levy was done with Holiday and already had another lover. He wanted Holiday gone but cared about his own public image too much to end the relationship.

Ehrlich hung about the nightclub scene until he found a photograph of Levy and White drinking together. Ehrlich recounted that:

“The defendant had a narcotics record. The evidence was chemically authenticated. The principal witness for the prosecution, Colonel White, was a cool and knowledgeable expert, resourceful under cross-examination, famed and popular as a dope fighter. The prosecutor had already cut a notch in his briefcase for this one.”

As the story goes, Ehrlich’s formidable cross-examination and the black and white photograph of Colonel White and Levy socialising together was enough to raise doubt as to Holiday’s guilt – and she was found not guilty.

Despite the acquittal, addiction eventually caused the untimely death of a talented, hopelessly caring, and beautiful young woman.

Thankfully, many would remember Holiday not as an addict or criminal, but as the New York Times put it: a woman with a “swatch of gardenias in her hair, her fingers snapping lazily with the rhythm, her head cocked back at a jaunty angle as she sang.”