Damien's first contact with the police came when he was 17. His girlfriend at the time and he decided to run away from home together. The first night, they broke into an adandoned house for the night. The police came and Damien was arrested and forced to take many psychological tests. He was then sent to Charter Hospital. While he was in Charter, he was diagnosed manic-depressive and given the anti-depressant drug Tofanil, which he took until he arrived on death row. Damien met Jerry Driver, chief Juvenile Probation Officer for the county, and a parter of Steve Jones. During an interview, Driver had been convinced that "Satanic" cults were behind many crimes in the area and was determined to put a stop to it. From then on, Driver would investigate Damien in several unsolved crimes in the area, but was never able to convict him.
After his release from Charter, Damien's life took a traumatic turn. His mother had divorced Jack Echols and remarried Damien's biological father. They moved to Portland, Oregon. After the move, Damien began to drink heavily. His parents called the police one night when he had locked himself in his bedroom and threatened to kill himself with a knife. He was again treated for depression and alcohol rehabilitation. He was released when he informed doctors that nothing they could do would make him feel any better. This time he returned to Arkansas after his release. Records in Oregon show that the authorities were informed of Damien returning to Arkansas, although there is no record of this information in the Arkansas office. Damien was staying with a friend on the condition that he return to school. The day that he went to get readmitted to the school, he was told he needed a letter from his parents. Driver arrested him as he was leaving the school grounds. Driver filed a complaint saying that Damien had violated his parole by leaving the care of his parents after he had threatened their lives.