One of the most important tools for the survival of any career criminal was not weapons, money, or connections, but their reputation. A reputation for violence would strike fear into anyone who would speak up to the authorities or caution rivals from challenging for territory. A reputation of philanthropic actions would garner good will with the community and the authorities, which would allow a gang to exist among the community for extended periods of time. A gangster in the 1900s needed to maintain a balance of these two distinct types of reputations to survive police investigations and thrive against rival gangs.

When gangsters like Jake “The Barber” Factor, Owney “The Killer” Madden, Mickey Duffy, and Al Capone chose an automobile, they chose a car to represent this balance of reputations. The car of choice was the Duesenberg Model J. The Duesenberg Model J, marketed as a car for the rich, powerful, and fully alive, was an image that these high-profile celebrity gangsters would pay any price to own.