"The Bug"
They also formed the lottery know as "the bug." In 1938 "the bug" was so popular that patrons pushed into the Ritz Café, owned by Shepherd and Matthews, to buy tickets and see the winning numbers. The crowd exceeded the building's capacity, pushing out the walls and a steel beam, collapsing the building on the crowd. 24 people were killed and dozens more injured. Police swore to action, but could turn up no witnesses. No action was taken.

Brotherly Love
Shepherd and his brother Snooks were indicted for the murder of Columbus gambler Fate Leeburn in 1946. Shepherd hired every available attorney in town including Albert Patterson and was acquitted. Snooks took the blame for the murder and was found innocent, claiming the shooting was in self defense.

Feeling the Heat
In 1952, as Phenix City was feeling the heat of community activists like Hugh Bentley, Shepherd and Matthews announced they were quitting the rackets and turned over a warehouse full of gambling machines. Though retired from running gambling clubs they rented their properties to other gamblers and later served 90 day sentences for leasing buildings for gambling. A wire tap established Shepherd as the leader in the Phenix City crime syndicate.

A Change of Heart
Shepherd invested his money from gambling in legitimate businesses, donating freely to churches and financing political campaigns. Shepherd's goal was to gain a reputation of good standing in the community for the sake of his children.