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, ExplainedMay 14
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 Life HacksMay 19
Why it’s so hard to save right now
Let's explore why saving feels so difficult right now, and how we can help you regain control.
Pittsburgh's BestMay 15
7 Summer Biking Events in Pittsburgh, From Group Rides to Races
Pedal in Pittsburgh at group bicycle rides, races, and special events featuring tasty treats.
Pittsburgh's BestMay 13
10 Summer Home, Garden, and Neighborhood Tours in Pittsburgh
Be your best nebby self and explore lush gardens, historic homes, and magnificent parks on these summer tours.
Pittsburgh's BestMay 12
10 Ways To Celebrate Your Birthday in Pittsburgh
Take a guided tour, learn a new skill, have a spa day, or play games with friends on your next birthday in Pittsburgh.
Pittsburgh Life HacksMay 8
Pittsburgh's Guide To Voting in the 2026 Primaries
What to know before you vote in Allegheny County’s primary election on May 19.
Pittsburgh HistoryMay 7
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's BestMay 6
15 Pittsburgh Music Festivals for Good Tunes and Community
It’s music festival season! Whether you’re into jazz, rock, punk, or folk, Pittsburgh has an event for you.
Food & DrinkMay 4
4 Pittsburgh Brunches We Don’t Want To Live Without
Whether you’re craving dippy eggs and home fries or a towering stack of pancakes, there’s a Pittsburgh brunch spot for you.
