In the late 1860s, Al Smith ran a famous saloon and gambling house at this location, 111 N. Dearborn. With his earnings from this establishment, Smith bankrolled the city's top madame, Carrie Watson, who ran the most glamorous brothel in the city until the opening of the Everleigh Club. After the Great Fire, Watson and Smith went their separate ways, with Watson becoming close with Sig Cohen, and Smith leaving town for New York City, where he spent the last 35 years of his life at the posh Gilsey House hotel. Continuing to operate in the underworld, Smith was heavily involved in prize fighting, managing many fights for John L. Sullivan, the first heavyweight champion of the world. He died in 1909.
The site of Al Smith's gambling establishment is now the CBS 2 Broadcast Center.