News media from around the world flocked to the Los Angeles Municipal Court, hoping to catch a glimpse of the infamous "madam to the stars" during Heidi's arraignment on August 9, 1993. Heidi retained criminal defense lawyers Anthony Brooklier and Don Marks to represent her. At Heidi's request, a plea of "not guilty" was entered on all charges. She was indicted a month later.

During the trial that year, Heidi's attorneys presented a persuasive argument claiming that officers entrapped her. Their strong argument caused a split among members of the jury. Some strongly believed she had been set up, whereas others believed she had been justly apprehended.

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To prevent a deadlock, some of the jurors decided to bargain in the hopes of coming to a mutual agreement. Finally, after four days of deliberation they reached a decision. On December 2, 1994, a grand jury found Heidi guilty on three of the five pandering counts, but innocent of the narcotics charge. Months later, Los Angeles Superior Court Judge Judith L. Champagne sentenced Heidi to three years in prison and a $1,500 fine.

When Heidi's lawyers learned that some of the jurors "traded votes" to reach a verdict, he appealed for a new trial. During the appeals process, Heidi remained free on bail. While out on bail she immersed herself in her new occupation, selling men's boxer shorts and other apparel at her newly opened store in L.A. aptly called "Heidi Wear."

In the midst of the state trial, federal proceedings began against Heidi. On July 28, 1994, a federal grand jury indicted her on 14 counts of conspiracy, income tax evasion and money laundering. Heidi's father, Dr. Paul Fleiss, was also indicted for having signed a bank loan of $1 million, allegedly under false pretenses, which was used to finance Heidi's Benedict Canyon home. Heidi and her father entered pleas of "not guilty."

Facing both federal and state charges proved to be a tremendous burden on her. In September 1994, she tested positive for methamphetamine and was ordered to a drug treatment center. It would not be the last time she was caught using illegal substances.

In August 1995, a federal jury convicted Heidi on eight counts of conspiracy, tax evasion and money laundering. It was her second conviction in less than a year. Dr. Paul Fleiss received three years probation. Heidi was eventually sentenced to 37 months in minimum-security prison, of which she served 20 months. After striking a plea bargain with the state, she received another 18 months for the pandering charges. Thus, Heidi received a total of three years in prison.

Throughout it all, Heidi never publicly revealed the names of her customers. According to Heidi's book, only two famous clients came to the forefront publicly during the court hearings. They were actor Charlie Sheen and Texas billionaire businessman Robert T. Crow who admitted to using her service. The identity of her other customers was left to speculation.