Numbers Gambling In Hill District

By David Rotenstein


“Numbers gambling is an informal street lottery that was introduced in the early 20th century in Harlem. By the mid 1920s. It had spread to cities throughout the United States, including Pittsburgh.”

Hill District Story

Who says that Pittsburgh is a boring city?
Listen to David’s story as he found some resemblance between his own childhood experience to an exciting, albeit illegal, activities that happened in this storied neighborhood in the 1930s.

Hi, my name is David Rotenstein. I’m a historian and folklorist and this is my Storyburgh story.

I’ve been collecting and telling Pittsburgh stories for about 30 years. I come from four distinct but related story collecting and storytelling traditions. The first is archaeology. As a kid growing up in coastal Florida, I’d collect bits of busted up pottery, or shell, bone, and other things that Native Americans had deposited there 1000s of years before my family arrived in Daytona Beach. I took that interest in collecting artifacts in archaeology to college with me where I majored in anthropology and archaeology. I became a professional archaeologist, and then went on to graduate school to study folklore and folk life, the second story collecting and storytelling tradition that informs my work. Folklorists collect myths, legends, folk tales, as well as folk music. We collect food ways we document old buildings and cultural landscapes; all in an effort to understand the artistic expressions that make sense of our daily world. The third story collecting and storytelling tradition I work in is history. Historians collect narratives in documents and we collect oral histories; all in an attempt to understand the distant past and make sense of the present. The fourth story collecting and storytelling tradition I come from is journalism. In graduate school, my professors told me that I was a good writer, and I was always looking for ways to help support myself while finishing up my coursework and then writing my dissertation. So I began writing for newspapers like the Philadelphia Inquirer, Charlotte Observer, and magazines. I write about blues music, folk music; I’d write feature stories, a whole host of articles to help pay my way through graduate school.

In the summer of 1992, I was working on an archaeological survey of the then proposed Mon Fayette expressway in Washington County, Pennsylvania. At the time, Pittsburgh newspapers have been crippled by a long running strike, initiated by delivery drivers. To help mitigate the impacts of the delivery driver strike and the shutdown to the presses, The Post Gazette had hired several news criers to stand in Market Square to keep the news out in front of the public and to keep the the brand name alive. I took a launch long lunch break it was definitely more than an hour and drove up from Washington County to market square to interview the town criers and to interview the then editor of the Post Gazette. That was my first foray into Pittsburgh story collecting and storytelling.

One thing that informs my story collecting and storytelling endeavors, is my desire to answer unanswered questions. Between 1999 and 2019, we lived outside of Pittsburgh, much of that time in the Washington DC area. When we move back to Pittsburgh and 2019 I brought with me a long running research project on gentrification and how history is produced and written in gentrifying neighborhoods. One story that is common in the in the research that I’ve been doing in gentrifying neighborhoods, is the history of numbers gambling.

Numbers gambling is an informal street lottery that was introduced in the early 20th century in Harlem. By the mid 1920s. It had spread to cities throughout the United States, including Pittsburgh. Here in Pittsburgh, it became entrenched in the Hill District, and was run by notable figures like Woogie Harris and Gus Greenlee. Gus Greenlee was a prominent entertainment entrepreneur who owned nightclubs, restaurants. He was a boxing promoter, and he was perhaps best known as the owner of the Negro Leagues, Pittsburgh Crawfords baseball team. Greenlee, like his contemporaries, couldn’t go into a bank and get a standard business loan to help pay for salaries, equipment, travel costs, and all of the other things that went into owning and running a professional baseball team. So, he used his proceeds from running one of the city’s earliest numbers rackets as a financing vehicle for his sports exploits.

After moving back to Pittsburgh in 2019, I began reading and rereading Pittsburgh histories, especially ones associated with the Hill District and that focused on numbers gambling. One of the books that I picked up in 2019 to learn more about numbers gambling in Pittsburgh was University of Pittsburgh historian Rob Ruck’s book Sandlot Seasons. Ruck interviewed surviving baseball players, team owners, and numbers racketeers to better understand the history of black sports in Pittsburgh. One of the people that Rob Ruck interviewed was an aging racketeer named Sam Solomon. Rob Ruck like historians before him, who had written about the history of numbers gambling in Pittsburgh, was keenly interested in an episode from the summer of 1930. On August 5th of that year, it seemed like everyone in the city of Pittsburgh had bet on a single number: 805. When that happened, the numbers bankers like Gus Greenlee and Woogie Harris struggled to scrounge up the money to pay off on the winnings. Many numbers bankers in the city took for the hills. Some of them left and never came back because they couldn’t pay off on the bets. Woogie Harris and Gus Greenlee, however, solidified their legendary status in the city by paying off on all of the bets. Ruck was able to interview Woogie Harris’s younger brother, the famous photographer Teenie Harris, and he also interviewed Charles Greenlee, Gus Greenlee’s son. One of the people that Ruck interviewed was an aging racketeer named Sam Solomon. Solomon had spent his entire life in Pittsburgh’s Hill District starting out as a bootlegger and graduating to numbers gambling. He was old enough to remember what happened in the summer of 1930 and when Ruck asked him about the 805 episode, Solomon replied, “805 was a burner. Where the hell is Jakie Lerner?”

Ruck didn’t follow up on Solomon’s rhyming answer with questions like who was Jakie Lerner and why was Jakie Lerner important to the story? And rock moved on to other aspects of 805 before going on to other parts of numbers gambling history here in Pittsburgh. Not liking unanswered questions I decided to go find Jakie Lerner and his story. I found Lerner buried in a modest Shaler Township Jewish cemetery and I began digging into the surviving documentary record associated with Lerner’s life. Lerner it turns out was a pretty important Jewish racketeer here in Pittsburgh, who like Solomon began as a bootlegger and graduated two numbers gambling. The stories I was collecting from Lerner’s surviving relatives and business associates began resonating with me on a personal level.

‘Though I’d never been involved in organized crime and numbers gambling, I did have a very vivid memory from the eighth grade when I and my family were whisked away by the FBI in a protective custody. We were taken from Daytona Beach to a hotel room in Atlanta, Georgia, while federal state and local law enforcement officials rounded up the conspirators who had sought to have my father killed. Turns out my father was involved in some shady real estate practices that had angered his business associates. When the FBI first learned this story, they initially thought it was this massive organized crime conspiracy. It turns out my father was little more than a petty thief. But nonetheless, it was a powerful memory that I had, that I could then you know, apply to what I was hearing from Lerner’s relatives who remembered being told to not talk about the family business, remembered seeing money being squirreled away through the family homes and remembered always being under the watchful eye of federal and local law enforcement officers.

My project in numbers gambling, the stories that I’m collecting, and the stories that I’m now starting to write will ultimately end up in a book on the social history of numbers gambling. Numbers gambling is a rich and important part of Pittsburgh’s social history. It informs much of the way that immigrants from the Deep South and from Europe, were able to adapt to a to a city that in some cases was ruled by Jim Crow, other cases by anti Semitism, or anti Catholicism. It’s an important part of the city’s history, with rich and colorful stories like the 805 story, and like the stories associated with notable racketeers like Gus Greenlee, Woogie Harris and even Jakie Lerner.


Curious about Jakie Lerner? Read more here on Pittsburgh Quarterly.

Story Credits

Story Coaches: Pamela Monk & Kay Bey
Videography: David Rotenstein
Web Producer: Will Halim

Disclaimer: the narrative expressed in the article is solely those of the author(s).
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