In 1987, a month before his 30th birthday, McNair broke into and stole from a grain storage facility in Minot, North Dakota. He shot two men when stealing from another place that same year, and one of the men who McNair shot was killed. He was eventually arrested for the crimes, but when being questioned by police, he took lip balm out of his pocket and slipped his hands out of the cuffs the police had restrained him with during the arrest. He escaped the police station with the officers pursuing him from behind. McNair managed to hide inside a building when police officers came in to take him back to the police station. McNair jumped out of a window and crashed into a tree, but was injured when the branch he landed on snapped. After time in the hospital, McNair was housed at Ward County Jail in Minot, North Dakota. While serving time there, he broke through part of a wall in his cell, but police officers who worked there found out about it. After being moved to the North Dakota State Penitentiary, McNair and two other inmates escaped by crawling through the ventilation shaft. He went around the United States for ten months, but was arrested again and the officers marked him as a bad inmate, and moved him to the Oak Park Heights prison.