Toothpick was a lieutenant of Le Paradox's gang and was sent to a place out West called "Cotton Mouth Bluff", in the year 1884 AD. Toothpick intended to steal gold from that year and then bring it back to the present in order to make him a billionaire. His love for gold started at a young age, as he grew up loving cowboy films and gold. Toothpick eventually became an Eastern European mobster who specialized in gold robberies.
Toothpick was hired by Le Paradox to eliminate Tennessee Kid Cooper. After arriving at Cotton Mouth Bluff, Toothpick staged a robbery and framed Tennessee Cooper. The staging was successful even though the robbery happened after Tennessee Kid Cooper had already been arrested. Toothpick stole Tennessee's cane, storing it away in a storage facility, which he converted from a gold mine. Bentley would follow Toothpick to the location of the facility. Then, when Toothpick went off to inspect his gold, Bentley and Murray let Tennessee into the mine, successfully stealing back his cane.
Later on, Toothpick loaded up all his gold on his train and attempted to travel back to the present, where the opportunity to be a billionaire awaited. However, Sly and the gang caught up to Toothpick, as Sly took him down in a fight on his train. Toothpick was eventually thrown off the train and stranded in the past forever.