Demolition began Wednesday morning at 1230 N. Burling St., Cabrini Green's last standing high-rise.
It marks the final stage of a years-long initiative to raze the housing project and signals the last chapter in the development's storied, troubled history.
Ald. Water Burnett (27th) was raised in a Cabrini Green building across the street from the final highrise and said he had fond memories of his time there.
"There was a cohesiveness. Everyone was related someway, somehow. Everyone looked out for each other. Everyone knew each other. And that type of family atmosphere will not be here anymore," he said.
The few remaining residents moved out of the now-vacated building on Burling in December. At one time, Cabrini Green was made up of 10 sections, built over a 20-year stretch starting in 1942, and was home to 15,000.
The homes became known for gang violence, deteriorating conditions and an unspeakable crime surrounding Girl X, a 9-year-old found strangled, raped and poisoned in a stairwell.
Crime in the complex was so bad that Cabrini made news nationally as the worst housing project in the country.
But some residents were undeterred.
They rallied around their home and organized efforts against crime. When the federal government mandated Cabrini's demolition, residents filed a relocation lawsuit and some refused to leave.
The homes came down nonetheless and people who lived their for years were forced to move out.
Development companies built new row houses in the area and talk of redevelopment on the mostly barren Cabrini property is now on the table.
The latest talks involve a proposed Target store on the site.
The retailer is looking to make a land swap with the Chicago Housing Authority to build a new store at the northwest corner of Division and Larabee streets, the Sun-Times reports.
"I think CHA is negotiating with Target trying to make sure that their residents over here get job opportunities, not only on construction, but permanent jobs inside the store," said Burnett.
A Target spokeswoman didn't confirm the news but she acknowledged the company is scouting new sites in Chicago.
Demolition to 1230 N. Burling St. will take about a month.