Life After Football
On November 11, 1994, Boles was arrested on charges of possession of drug paraphernalia and petty theft and wound up in jail in Naples, Florida.
Boles discovered at age 27 that he had not been reared by his biological father. He soon thereafter started experimenting with cocaine. After football ended, he worked various jobs such as construction and working at a grocery store. He then started selling drugs and then using his product. This led him to a series of arrests, prison stays, and homeless periods. In 2003, two former teammates tracked him down and set him up with a job at a car wash. However, Boles fell back into his criminal ways. Boles was convicted of robbing an elderly couple and was sentenced to three to fifteen years in prison. He was released into a work program. He also found himself at the Elmhurst Home, Inc. substance abuse treatment center in 2006. The residential treatment center has since 1972 been used to host about 100 recovering addicts at a time providing Narcotics Anonymous and Alcoholics Anonymous meeting places, military style roll calls, daily tasks, and progress logs.
Physically, in 2006, Boles was described as starting to gray, missing two top front teeth and suffering from an arthritic knee. He stood 6 feet 2 inches (1.88 m) and 190 pounds (86 kg; 14 st). He had a 21-year-old daughter and kept in touch with his mother. His stepfather had died in 1994.
Boles was arrested in Ypsilanti, Michigan on September 9, 2007 and pled guilty to one count of receiving and concealing stolen property. He was sentenced to serve two to five years in prison for receiving and concealing stolen property in violation of his parole in Washtenaw County Circuit Court. He had previously served six months in prison for unarmed robbery before he was paroled in 2005. Boles' most recent infraction occurred when with an outstanding warrant, he provided a false name to officers investigating why he was blocking traffic with a car they would find out had been stolen from Detroit, Michigan. He had been attempting to converse with sidewalk pedestrians while purchasing drugs.
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