Simon chose to not return to the military until he had straightened things out for his family. His brother, Tommy, was addicted to drugs and had been stealing from their mother to support his habit. Returning home on leave in January 2003, Simon found his mother and brother had hit rock bottom. He eventually was accepted into the Special Air Service. Simon used to be an apprentice butcher at a grocery but joined the military after the September 11 attacks occurred. At one concert, his father made him laugh at the death of a prostitute who had overdosed on drugs. Simon's father would sometimes take him to the Bone Lickers concerts. When he and his younger brother Tommy grew older, Tommy would always wear a skull-mask at night to scare Simon.

His father often brought dangerous animals back to their home and taunted him with them, even going so far as to force Simon to kiss a snake. Simon Riley had a very traumatic childhood while growing up in Manchester, England because of his heartless father. 1.3.6 The Search for Vladimir Makarov and Death.1.3.4 Infiltration of the Russian Oil Rig / Rescuing Prisoner 627.