Jerry’s Pizza, the Heart of the Hill District

Think of Jerry’s Market and Pizza Shop as Pittsburgh’s real-life version of one of the friendliest establishments on TV. “Walking into Jerry’s is like walking into Cheers,” said Shawn Thomas, Lending Team Leader for Bridgeway Capital. “Everybody knows everybody. You’ll see councilmen and judges. Everybody’s friendly, the food is flowing, and community leaders are talking about what’s going on in the community and how it’s changing for the better.” 

That community is the Hill District, and after you spend a few minutes inside Jerry Hughes’ shop, you might think he knows every resident. You wouldn’t be far off. “I was born and raised in the Hill,” he said. “We’ve had our ups and downs, but it’s been a thriving community from day one.” 

Hughes’ idea to open a pizza shop came in the early 1980s when he befriended Angelo Posteraro, of Angelo’s Pizzeria, a longtime family-run restaurant in Bloomfield. “Angelo said, ‘You ain’t even got to be a good business person. You make a good pie, and it’s gonna sell.”

Hughes has the good pie part down, but, of course, keeping a shop alive is a little more complicated than Angelo joked it was. Financial support from Bridgeway Capital has helped Hughes with day-to-day expenses, supplies, utilities, and payroll. “It’s been the wind underneath my wings to keep me flying,” he said. 

During Covid, when Hughes wanted to expand his business to include a lounge, Bridgeway was able to provide a tailored loan to help his cash flow — so that he has even more space to host the community members that flock to his restaurant for hot pizza and friendly conversation. “We want to make sure he can be there for a very long time,” Thomas said.

That happens to be Hughes’ plan too. “I just want to be able to keep making a good pie,” he said. “And bring my grandkids into the fold, where they understand that there’s something at the end of hard work. And then they bring their new fresh ideals to even make it greater.”


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