The free-agent bootlegger
In restaurants and hotels, even so-called honest houses which officially complied with the law of the land, enterprising waiters, elevator operators, desk clerks, concierges, valets, and other employees acted as bootleggers independently of the syndicates. They purchased their liquor from other retailers, in smaller amounts, and offered it to customers by the drink in the restaurants and coffee shops, and sometimes by the bottle, with a profit margin added, to registered guests. These entrepreneurs often maintained a relationship with a nearby speakeasy, from which they received payment for referring customers.
The free agents, being independent of the syndicate, were outside of its protecting arm, though they frequently sold the syndicate’s products. It was up to them to bribe the local representatives of the law, either through cash or more often through free liquor to the neighborhood policemen. The policemen frequently responded by directing others toward the bootlegger in a mutually beneficial arrangement. Those in the know found that the coffee they had ordered was a shot of whiskey served in a coffee cup, or the glass of iced tea was in fact a Scotch highball. Scotch has a pungent smell, and the absence of detection indicates that the bootlegger’s employer was at the very least aware of the activity.
Free agents operated in barber shops, where daily visits of customers seeking a shave was not an unusual activity which attracted attention. The same was true of cigar stores, which in the 1920s were on nearly every city block. Cigar stores were also havened for illegal gambling with cards and dice in their backrooms, activities which predated Prohibition by decades, and which readily accompanied the new vice of illegal drinking. Cab drivers also found bootlegging to be a profitable enterprise, tacking on the cost of a quick drink to the fare, and receiving a larger tip for the service.