I found this man wandering back and forth all alone near a halfway house smiling to himself. I don’t know if he was a resident or just waiting for someone. His clothes struck me as odd. He was wearing a coat and tie – very unusual for Uptown in this era – with white socks and shoes that had holes in them. Holes in shoes were not unusual. Enlargement will show a white sock sticking out the side of the camera-left shoe where the upper part the wingtips had separated from the sole. Nothing added up to the impression this man wanted to create. I concluded that he was a poor, lost and lonely human being, struggling as best he could to find a job or a friend. The photo was taken at 909 West Wilson in Chicago’s Uptown neighborhood in 1975.

He probably concluded that I was a struggling young photographer who couldn’t afford a fill-flash. He would have been right. The strong backlight made the contrast in this scene exceed the contrast capabilities of the film.