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How Bootleggers & Bullets Brought Nightlife to the Hill

Posted on February 22, 2023   |   Updated on September 30, 2025
Francesca Dabecco

Francesca Dabecco

Hill District map drafted in 1917 by the Irene Kaufmann Settlement showing “The Neighborhood’s Negative Forces.” Map courtesy the Oliver M. Kaufmann Photograph Collection of the Irene Kaufmann Settlement, University of Pittsburgh Library Archives & Special Collections.

Hill District map drafted in 1917 by the Irene Kaufmann Settlement showing “The Neighborhood’s Negative Forces.” Map courtesy the Oliver M. Kaufmann Photograph Collection of the Irene Kaufmann Settlement, University of Pittsburgh Library Archives & Special Collections.

The Hill District was a thriving neighborhood 100 years ago, known as much for its nightlife as its rich, cultural heritage — until the city leveled it to build the predecessor to PPG Paints Arena. Learn the history of a predominantly Black neighborhood and how two white brothers used nefarious means to bankroll big portions of it.

Hear a bit of Bootlegging History
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