May as well start posting these here too. 1950 - 2020. Chicago, corner of Ashland Ave and Jackson Blvd. This stretch flipped from 1880s mansions to boarding houses (mostly for medical students) and labor unions then back to fancy townhouses.
The still-standing Richardsonian Romanesque mansion on the right is the Chalmers House (1885, Treat & Foltz). William Chalmers married Joan Pinkerton - yeah, Allen Pinkerton’s daughter. Now their home sits on Union Row under the tower of @CMRJB’s office (Walter Ahlshlager, 1928).
Two of the since-demolished mansions were built in the 1880s for Chicago Board of Trade members, Ulric King & Sanford Scribner, but the wealthy fled the neighborhood quickly (and at a $$$ loss) - by 1910 these homes had been sold and turned into boarding houses.
Before that though, King, Scribner, and Chalmers were buddies with Chicago Mayor Carter Harrison Jr. - he lived across the street. When the Mayor was assassinated in 1893, Chalmers was one of the first to respond.
Mayor Harrison was an avid cyclist - they had no idea how good they had it, you’re crazy to bike down a car sewer like Ashland today.
The rich moved out of these buildings, medical students moved in, and then in the 1950s it became a dorm for Coyne College (a trade school). There are truly a bizarre number of postcards depicting what was a random trade school dorm.
The Chalmers house (315 S. Ashland) became a nursing home and then a (pretty questionable imo) religious rehab/addiction center. Also a puppy was rescued from within its walls in 1950. Today it is once again apartments.