Heidi Fleiss: The Million Dollar Madam

Immediately before serving her federal prison sentence, Heidi tested positive again for drugs. She was temporarily sent to jail and then ordered to attend a drug rehabilitation clinic. She remained at the clinic until the day she was to be transferred to the federal prison in September 1996.

Pleasanton Penitentiary proved to have life-altering effects on Heidi. According to Duncan Campbell's article "Don't Call Me Madam," it "was a frightening and humiliating experience." She was often harassed by the female inmates, which at times resulted in fights. Heidi was forced to literally defend her life on occasion. 

According to Allan, Heidi was pressured to prove her toughness to other inmates by standing up to a female prison officer who remanded her for moving a locker in her cell. In response, Heidi hurled two chairs over the officer's head. In an interview with Allan, Heidi claimed that if she didn't do it there would have been "serious consequences" and possibly become someone's "little prison bitch." The prison was known to have a high percentage of lesbians, some of whom would force girls into having sex.  

Heidi ended up spending 63 days in a special housing unit where the more hostile prisoners were confined to small concrete cells for the duration of their punishment. It was not the last time Heidi would be sent there. On one other occasion she was confined there for 47 days for breaking prison rules.

Heidi passed much of her time in prison reading and playing chess with some of the other inmates, most of whom she taught to play the game. Heidi was an exceptional chess player, having won two city chess championships in a row as a child. She also befriended a few of the inmates. During an interview with Larry King, Heidi said she forged a close bond with one particular woman named Sylvia, who was serving time for drug charges. Sylvia, seasoned by years of imprisonment, gave Heidi advice that helped her through her most difficult periods.

In November 1998, Heidi was released from prison and placed in a halfway house in L.A. for the duration of her sentence. However, she had difficulty getting acclimated to her new surroundings and after several days she expressed a desire to return to prison. It is believed that her reason for wanting to return was due to safety concerns. The authorities approved her request and Heidi eventually returned to Pleasanton to complete her sentence.