Simon was a very nervous and paranoid man by nature, having a noticeable stutter in his high-pitched voice sometimes. He was one of the lower members of the criminal organization 101 working directly under James O'Reilley to distribute meth and take in income for the group.
Isabelle Knight Edit
Simon was put in charge of Isabelle Knight, a meth addict that slowly became dependent on Simon giving her meth to sell and use. He gave her a deal; sell bags of meth and in return, get one or two for personal use. This worked fine until Simon began to slip up on the money he owed back to James and Mav Doretto, who became increasingly frustrated by his mistakes. On one occasion, James cut out Simon's eye in front of Isabelle as punishment and to set an example for the both of them. Since that moment, he forced everyone to call him "Leon" to further protect his identity, worried that the cops were on to him about the meth. His paranoia increased until it was too much of a liability for 101 to have around.
After the mistakes and missing meth and money continued to be a problem for Simon, Mav and James decided to deal with him. On December 17th, they took him out in a car to a remote peninsula on the West coast of the island. They forced him to his knees and started to cut off his fingers, but halfway through, Simon punched James, then took his gun and held James between him and Mav's shotgun. After trying and failing to yell through his gag, he briefly exposed his side out from behind James and was shot by Mav. Some of the bullets managed to catch James, but he was mostly uninjured. Mav finished the job by cutting the rest of his fingers off and pulling his teeth out, then pushing him out into the current.