Chris Krauss submitted this unusual ashtray for the Project. I knew nothing about it, so asked Dwayne Kling, author of "The Rise of the Biggest Little City." His response:

Very interesting picture!! My educated GUESS. Leo Schwarz opened the first bar in Harolds (in 1941) and was the first bar manager at Harolds Club so I would say that very possibly Mr. Schwarz called the first bar that he opened "Leo's Bar" and had ash trays made that would publicize both the bar and Harolds Club. The bars were owned separately by Raymond I. Smith (Pappy) and he gave monetary rewards and bonuses to his early day bar personnel. That is what makes me think that Leo was trying to generate more business for his bar (which would in turn increase his bonus) that was located in the north east section of Harolds Club.
But, as I say--Just a guess. Dwayne