He was the founder of the Broadway restaurant-cabaret club "Churchill's", located on Forty-Ninth Street, which became one of the most popular establishments in New York City for over a decade prior to Prohibition.
He retired at the rank of police captain around 1904 and, at the suggestion of friends and family, eventually entered the restaurant business.
His menu of chops, potatoes and ice cold beer attracted very large crowds and soon found his establishment too small to accommodate his customers.
He sold his shop and bought a bigger place of Forty-Sixth Street, which seated 350 people, but this too proved too small and he eventually opened "Churchill's" in 1909.
He was invited to Washington, D.C. and personally approached President Warren G. Harding to offer him the position of Prohibition Administrator for the state of New York.
Instead of the hostesses, I employed thirty boys, one of them the late Rudolph Valentino, to dance with women who came unescorted for luncheon".