Every once in a while I've heard stories about how in some parts of the city some buildings have several numbers. It denoted different addresses over the years at least until the street numbering system had been standardized early in the 20th century. It didn't take a city planner to make this change but a grassroots person who was frustrated by this chaos.
Imagine what one person can do, although in his case he had family connections. You will see if you read this WBEZ article.