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.
How Bootleggers & Bullets Brought Nightlife to the Hill
Posted on February 22, 2023 | Updated on September 30, 2025
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.
see more:history
Share article
Stay connected to City Cast Pittsburgh and get ready to join the local conversation.
Pittsburgh, Explained
Pittsburgh, ExplainedApril 17
Try This Pittsburgh Crossword Puzzle
A crossword puzzle all about Pittsburgh news and fun facts.
Pittsburgh, ExplainedApril 14
The Baltimore Banner Buys the Pittsburgh Post-Gazette
Both the Pittsburgh Post-Gazette and Pittsburgh City Paper will continue in 2026.
Pittsburgh, ExplainedMarch 26
Stay in the Know with City Cast Pittsburgh
Subscribe to our FREE daily newsletter and podcast made for Pittsburghers by Pittsburghers.
Pittsburgh, ExplainedFebruary 23
What We’re Loving About ‘The Pitt’ So Far
City Cast Pittsburgh’s favorite local references and missed opportunities in season two of HBO Max’s “The Pitt.”
Pittsburgh, ExplainedFebruary 20
7 Ways To Learn About Black History in Pittsburgh
Learn about Pittsburgh’s Black trailblazers, activists, artists, and sports teams at these local landmarks.
Pittsburgh, ExplainedFebruary 18
Will Pittsburgh Build A New Football Stadium?
The Steelers are already planning for their next arena, Allegheny County Executive Sara Innamorato confirmed to City Cast Pittsburgh.
Pittsburgh, ExplainedJanuary 27
Ways To Support Pittsburgh’s Immigrant Communities
Trainings, mutual aid, family support, and other resources to help immigrant communities as ICE activity escalates nationwide.
Pittsburgh, ExplainedJanuary 21
Mayor Corey O’Connor Talks Budget Gaps, Filling Storefronts & Fresh Ideas for Downtown
City Cast Pittsburgh podcast host Megan Harris sits down with Mayor Corey O’Connor at the City-County Building.
The latest in Pittsburgh
Pittsburgh HistoryApril 24
Think You Know Pittsburgh Neighborhoods? Take This Quiz
How well do you know Pittsburgh neighborhoods and the surrounding areas? Take our quiz to find out!
Pittsburgh Life HacksApril 22
What to Do When You Get Scammed
When the scam involves money or your accounts, your first move should be to contact your financial institution.
Food & DrinkApril 17
10 Food and Drink Festivals in Pittsburgh This Spring
Mark your calendar for Mac and Cheese Festival, Vegan Restaurant Week, Strawberry Pretzel Standoff, Pittsburgh Pizza Olympics, and more.
Food & DrinkApril 13
Where Can You Get a Good Bagel in Pittsburgh?
The City Cast Pittsburgh team tried some of Pittsburgh’s best bagel shops. Dig into our favorites.
Pittsburgh's BestApril 10
Free Parties, Concerts and More NFL Draft Events in Pittsburgh
Party for the NFL Draft in Pittsburgh with a music crawl, free fan festival in Point State Park, Slappers N Bangers dance party, Pitt Blo...
Food & DrinkApril 8
The Michelin Guide is Coming to Pittsburgh. How Does it Work?
The prestigious restaurant guide is expanding to the Great Lakes region, including Pittsburgh. What restaurants should get a Michelin Star?
Pittsburgh's BestApril 7
1,000 Things We Love About Pittsburgh: By the Numbers
City Cast Pittsburgh readers and listeners tell us what they love about living in Pittsburgh.
Food & DrinkApril 1
5 Food and Drink Pop-Ups Worth Tracking Down in Pittsburgh
Get Malaysian goodies, deep dish pizza, veggie-packed Korean bowls, creamy matcha drinks, and more at these Pittsburgh pop-ups.
