Dorothy's journey to that moment began with a relationship with a partner who was addicted to crack cocaine. With her encouragement, he entered treatment, remaining in a program for almost 8 months. Unfortunately, once he left treatment, Dorothy's boyfriend relapsed and continued using crack. One day federal agents raided Dorothy's home, where she lived with him.

Although law enforcement officers found no drugs or weapons on the premises, both Dorothy and her boyfriend were arrested and charged with conspiracy to deliver cocaine based on her boyfriend's alleged involvement in a large-scale drug operation as a driver. Dorothy was completely unaware of any such activity on his part.

Charges against Dorothy were initially dismissed, but several defendants in the conspiracy later made a deal with the prosecutor to reduce their own sentences by providing information to assist in the prosecution of others. They subsequently alleged that Dorothy had delivered small packages of cocaine to local street sellers. On the basis of this testimony Dorothy was charged and convicted of conspiracy to distribute the total quantity of drugs involved in the drug operation, and served six years in prison until she received clemency.