The Copelands were in Arkansas for less then a month before Ray was arrested for cattle theft. Charged with grand larceny, he was convicted and sentenced to one year in jail. Upon his release from prison, Ray moved his family to Rocky Comfort, Missouri. The change in scenery did not help and in 1951, Ray was again arrested for cattle theft. He was sentenced to manual labor on the judges farm.
In 1953, Ray moved his family to Illinois. Over the next eight years the Copelands moved from town to town and Ray was arrested on at least three separate occasions for writing bad checks. Fines and jail time did little to deter Ray and he continued to dabble in illegal activities. In 1961, Ray paid for 20 head of cattle with a $2,960 check. The seller soon discovered the check was no good and Ray was arrested and sentenced to nine months behind bars. Directly after his release, Ray passed another bad check during the purchase of 19 head of cattle. He was again arrested and sentenced to another nine months in jail.
After his last stint in jail Ray finally came to the realization that something needed to change. He was spending more time as a prisoner than he was a free man. Unfortunately, rather than change his actions he ultimately decided he needed to change his methods. He needed to formulate a new game plan and he decided to go straight until he could figure out the details.
During the summer of 1966, Ray decided it was time to move once again, and he took his family to Missouri. The following year, the Copeland clan purchased a small farm with 40 acres of land. They paid $6,000 for their new home, which was located in Mooresville, Missouri. They were in desperate need of money, so Faye soon took a job at Midwest Quality Gloves Corporation.
Over the course of the next several years many of Rays neighbors began to loathe him. They viewed him as a penny-pinching old man and several suspected he beat his wife and children. His wife and kids would verify these suspicions many years later.