Filed Under gambling

Numbers Gambling

Illegal lottery played a central role in Hill economy and culture

For much of the twentieth century, numbers gambling was a prominent role in the Hill District’s economic and social landscapes. The street lottery immortalized in August Wilson’s plays and Hill District oral traditions arrived in Pittsburgh in the early 1920s. Within a decade it had spread from Hill District barber shops, pool halls, and newsstands to every corner of the city. It spawned legends and financed the rise of the city’s rich entertainment and sports industries. 

Informal lotteries thrived in Black communities since at least the 1860s. The most popular, known as policy, evolved from betting on the outcomes of official state lotteries. Later gambling entrepreneurs opened betting parlors where people could bet on combinations of digits on buttons or balls drawn from burlap bags and wire cages. Pittsburgh newspapers began reporting on policy rings here during the 1870s.

Policy, however, was easy to rig and cheating was rampant. Thus, Harlem numbers racketeers developed a system for calculating the number that players believed was incorruptible, i.e., it couldn’t be fixed like earlier street lotteries. Instead of being drawn from a container, the daily number was based on a known figure published in the financial pages of daily newspapers - popular choices included the volume of shares traded on the New York Stock Exchange, or the daily balance of the U.S. Treasury.

Bettors played the game by simply selecting a three-digit number and paying a penny, nickel, or dime to a bookie called a “runner” who recorded the the number on a slip of paper. Because the daily number was unpredictable and publicly-known, consumer confidence and participation soared. With odds of winning at one in 1,000 and payouts for winning numbers at 600-to-one, a millworker or other laborer could rake in several days’ pay (or more) in a single lucky "hit."

By 1920, a new class of Black racketeer was emerging in American cities, built on the popularity of the new numbers game. Many started their careers in bootlegging and graduated to gambling. That’s the route William A. “Gus” Greenlee took after returning to Pittsburgh from serving in World War I.

Born in 1895, Greenlee was a North Carolina native who came to Pittsburgh in the 1910s. He lived with relatives in Uptown’s Quince Alley while working as a driver for an undertaker and automobile dealer. After the war, Greenlee came back to Pittsburgh in 1919 and went into the taxi business on his own. A year later Prohibition went into effect and Greenlee began moving liquor and beer throughout the city.

William A. “Woogie” Harris was a Pittsburgh native born in 1896 who also had an entrepreneurial bent. He and his family ran several entertainment and hospitality businesses in the Hill, including a boardinghouse and an indoor golf course.

Numbers gambling offered pathways to, or at least the hope of, a better life...Numbers employed thousands of workers throughout the city, and provided the capital to found some of the city’s best-known businesses

Numbers gambling arrived in Pittsburgh sometime in the 1920s. The specific person who introduced the game to the Steel City has been lost to history - it’s likely that an itinerant musician, traveling baseball player, Pullman porter, or industrial laborer showed locals how to calculate the daily number published in newspapers. A Hill District resident working temporarily in New York City, like Richard Gauffney was known to have done in the early 1920s, also could have brought the game home.

Becoming a numbers baron ("bankers" as they were known) involved assembling a crew of runners (bookies) and writers (mid-level managers) to collect money and the slips of paper on which bettors' numbers and bet amounts were written. It required entrepreneurial skills and an extensive social network, two things Greenlee and Harris had begun building during Prohibition.

Though Pittsburgh newspapers didn’t begin reporting on numbers arrests here until the late 1920s, local numbers rackets likely were active by 1923. That’s the year that Woogie Harris bought the Crystal Barber Shop at 1403 Wylie Avenue. Owned by master barber Frank Belt, the Crystal Barber Shop was a perfect “front” (a legitimate business) behind which Harris could run a numbers racket.

One year later, Greenlee entered the entertainment and hospitality business in the same block at 1407 Wylie Avenue. He and bartender Charles Williams opened “The Avenue.” Two blocks down at 1213 Wylie, Greenlee and musician and entertainment promoter Thomas “Kid” Welch took over the former Collins Inn space after its owner Henry Collins ended up imprisoned on liquor charges. 

Greenlee and Harris, along with their friends Gauffney and William “Bill” Snyder quickly established more front businesses in the Hill and built up an extensive network of runners and writers. At this point, numbers was an exclusively Black racket owned and operated solely by African Americans. 

But the Hill was a multi-ethnic community teeming with European immigrants who also liked to drink and gamble. Early studies of vice by the Irene Kaufmann Settlement published in the 1910s and 1920s showed dozens of speakeasies, gambling joints, and brothels throughout the Hill. Jews from Eastern Europe and Italians also built organized crime networks there. Like Black migrants from the Deep South, these groups suffered from antisemitism and anti-immigrant biases that prevented entry to better jobs, housing, and education.

Bootlegging and numbers gambling offered pathways to, or at least the hope of, a better life. Greenlee had been tight partners and friends with the Tito boys: Joe, Frank, Robert, and Ralph. The sons of Italian immigrants, they ran a large bootlegging operation. Harris and Gauffney had employed white runners among their earliest numbers employees. 

By 1930, Jews, Italians, Irish, and other immigrant groups had created their own numbers rackets. Over the next 50 years, numbers employed thousands of workers throughout the city. It provided the capital to found some of the city’s best-known businesses, including sports teams (the Crawfords and Grays baseball teams and the Steelers), Latrobe Brewing Company (Rolling Rock beer), and even Daily Juice. 

And, just like it did in Harlem, Washington, D.C.’s U Street Corridor, and Chicago’s Bronzeville, numbers provided the seed money for Pittsburgh’s jazz entertainment venues. Nightclubs like the Crawford Grills relied on numbers money to open their doors and they provided ways to hide illicit revenues from tax collectors. 

When Greenlee died in 1952, he and Harris had joined the top tier of Black racketeers in the United States. The National Brotherhood of Policy Kings ranks included Ellsworth “Bumpy” Johnson, Ed Jones, and Caspar Holstein.

By 1950, about the time that the intersection of Wylie and Fullerton had been dubbed the Crossroads of the World, Pittsburgh was a numbers city. Edith Robinson, a Black woman from Westmoreland County, was visiting her mother in Pittsburgh when she wrote to her future husband who owned a Washington, D.C., laundry with his four brothers. The July 4, 1950, letter, reproduced in a 2013 family memoir, included the apt line: “Pittsburgh is still the same: Wine, Women and Numbers!”


Pittsburgh Courier Headline Pittsburgh Courier headline detaling developments in a 1933 lottery case against Gus Greenlee. Judge Sylvester Snee dropped the charge against Greenlee, citing a lack of evidence. Source: Pittsburgh Courier Date: March 18, 1933


1403 Wylie Avenue, Pittsburgh, PA | Location is approximate; sites associated with this story were destroyed during urban redevelopment projects in the 1950s.


David S. Rotenstein, “Numbers Gambling,” Hill District Digital History, accessed June 17, 2024,