Homewood was founded by Pittsburgh’s wealthiest families, but it eventually became one of the city’s poorest and most racially segregated neighborhoods.

The change didn’t happen overnight. Leon Haley, 85, moved to Homewood when he was 6, and remembers it being a stable, mixed-income community. He grew up on Mt. Vernon and Kedron streets, attended the now-closed Belmar Elementary School and graduated from Westinghouse High in 1951. He was the seventh of 13 children and the first to go to college. His father and mother had migrated from Virginia because “there weren’t great opportunities in the South for African-Americans.” They found work as a laborer and housecleaner, respectively.

“There wasn’t much money, but what they had, they put into caring for us,” Haley said. “We were poor, but we never had the perception of being poor.”

Haley has warm memories of his youth. He played kickball and basketball with his friends and went to the movies a lot — there were two theaters in Homewood, after all — though he always had to be home “as soon as it would get dark.”

“This was a very stable neighborhood,” Haley said. “We developed a kind of community spirit here in Homewood in those days.”

Stable, safe and intimate is how a lot of people in Haley’s generation describe Homewood.

The neighborhood was founded by Judge William Wilkins in the 1830s, who also served as a U.S. senator and secretary of war. “Early Names And Old Landmarks,” written by Annie Clark Miller in 1924, describes the property as having “massive stone pillars … in the midst of a magnificent grove of trees.” The mansion was demolished in 1924, but the community had already established itself as a getaway from Pittsburgh’s smoky downtown, attracting well-off residents.

Industrialists like Andrew Carnegie and George Westinghouse built massive estates here. But as the 20th century approached, these wealthy magnates and their families left, and their land was sold or converted into smaller plots. German, Italian and Scots-Irish immigrants came to work in the city’s manufacturing sector, attracted by the flat land, cheap housing and easy access to transportation.

Around the same time, African-American families began to move in and establish themselves. Haley remembers the community being mixed racially in public spaces, but still segregated in places like pools and theaters.

“It wasn’t where you were told that you had to sit as an African American, as a black person, in the back. It was almost like: that’s what you do,” Haley said. “So we grew up having to sit somewhat in the balcony or in the back of the theater.”

But Homewood was also where some of Pittsburgh’s most prolific black artists, athletes and writers grew up. Westinghouse High School is the alma mater of pianists Errol Garner, Ahmad Jamal and Mary Lou Williams; Chuck Cooper, who went on to be the first black player drafted into the NBA; and jazz composer Billy Strayhorn.

The Hill meets Homewood

In 1949, the city announced plans to build what the Associate Press called a “revolutionary rain-defying amphitheater.” The facility would originally house the performances of the Pittsburgh Civic Light Opera Association, and be known as the “Civic Arena.”

The project was planned for the Lower Hill District and by 1961, when it was officially opened, it had displaced 8,000 families living in that neighborhood.

“Some moved further up the Hill where housing was provided,” said Heinz History Center Director of African American Studies Sam Black. “Some moved to East Liberty, but a larger [number] moved to Homewood.”

Most of these families were lower-middle class and African American. Black said they were promised money to help move, but rarely received it, resulting in poor conditions at their new homes.

“You have multiple families living in packed-in homes,” Black said. “And so you begin to have this sort of shift from a predominantly white community to a black community.”

The arrival of so many black families startled white Homewood residents, said Black, and coincided with “white flight,” or the movement of white families to the suburbs.

Those shifts are reflected in a 1937 Home Owners’ Loan Corporation map that ranked Pittsburgh neighborhoods by their desirability. It’s known as one of the original examples of “redlining,” a racist real estate practice that prevents minorities from acquiring home loans. Parts of Homewood and other now- predominantly black neighborhoods were ranked as third or fourth-grade locations, or the least valuable communities.

William Baker, who has owned Baker’s Dairy in Homewood for the past 54 years, said he remembers an Italian business owner trying to sell his corner store when “a lot of black people started moving here.”

“They wanted to sell immediately,” Baker said. “Then a lot of prejudice started ... this area started changing.”

Drugs and deterioration

Those trends continued after the assassination of Martin Luther King Jr. in 1968, when riots across the city led to the arrests of 1,000 people and the looting of more than 100 businesses.

In 30 years, Homewood’s population dropped by more than half to 9,000 two decades ago. The neighborhood now has a nearly 60 percent vacancy rate.

Geraldine Massey grew up in Homewood. Her former brother-in-law, John Edgar Wideman, wrote about the neighborhood in award-winning novels. Massey recently visited a home she once lived in with her ex-husband, Robby Wideman, and said she remembers when the community started to decline.

“It started to change in the late [19]80s, early ‘90s,” Massey said. “The guns came into the community, crack cocaine came into the community.”

Robby Wideman was put away for years after he participated in a robbery that led to a fatal shooting in 1975.

Wideman’s sentence was commuted in May and he was released last month. His older sister, Laticia El, said his story became more common in Homewood as the War on Drugs took hold. The phrase is used to describe the government-led push to remove illegal drugs from communities. But the campaign focused on criminal punishment, and it disproportionately targeted young black men. Nearly a generation of them were taken from neighborhoods like Homewood and put behind bars.

“You can talk to almost any child and if their father is not in jail, their uncle, their cousin, their brother, every family has been affected,” El said.

She hopes when her brother and other formerly incarcerated men return, they’ll mentor young people and help them forge a path much different than their own.

This story is Part 1 of a series exploring how Homewood, and residents who have spent time behind bars, are trying to rebuild after the War on Drugs.