It is unknown how Simon gained possession of Herbie but after failing to win races for him he decides to send him to the junk yard.
He shows a complete dislike for the little car but after seeing him do incredible things he didn't do when he had him he becomes determined to learn the car's secret. He soon finds Herbie's creator Dr. Gustav Stumpfel and persuades him to build another car like him only to have an evil competitive personality, he calls him Horace.
After cutting Stumpfel, Simon decides to eliminate the competition by destroying Herbie and sends Horace and his right hand man Rupert to carry it out. However when he discovers Herbie has been rebuilt he decides to settle this in road race between the two little cars. "The winner takes home both cars, to do what he wants."
Using modifications, He gains most of first place but his evil little car fails to win the race. Horace becomes so angry with losing that he tries to destroy Herbie again only to miss and go off the edge of a dam.
Simon becomes upset over the loss of his car and is later arrested by the police along with Rupert.