Under the Willow

The northeast corner of Monroe and Wells was the most notorious location in pre-Fire Chicago. From 1858-1868, Roger Plant ran a brothel and resort known as "Under the Willow," due to the willow tree that stood at the corner, under which Plant would ceremoniously dump liquor and trash. The windows of Under the Willow were covered with blue shades, upon which was written the famous catch-phrase he popularized, "Why not?"

Every sort of vice and criminal behavior took place at Under the Willow, and it was "one of the most talked about if not actually one of the wickedest places on the continent." It included a saloon, three brothels where men were typically robbed at knifepoint, white slave holding rooms, and cubicles which streetwalkers could rent and use to host their clients.

Plant himself was an Englishman, not more than an inch over 5 foot tall, and was dominated by his 250 lb. wife, who ran the brothels at Under the Willow. In 1868, Plant left the place and bought a house in the country, where he reportedly lived a serene life on the fortune he had made in Chicago. Several of his many children remained in Chicago and were active in the underworld into the 20th century.

The site is today a beautiful garden in front of the Northern Trust Building. There do not appear to be any willow trees on the property.