The eighth installment in a series on Oak Park housing history as it relates to diversity and equity:
Roberta “Bobbie” Raymond, in her 26 years of heading the Oak Park Housing Center (OPHC), epitomized the moral and practical policy tensions around race, housing and power in Oak Park. Her actions and beliefs as the lead voice of managed integration demonstrated that, as much as Oak Park was breaking new ground on inclusionary housing 60 years ago, it continued to face persisting contradictions around race, democracy and class interests — in our schools, housing reform, policing, and in the usually unspoken but persisting question of how many Blacks should be included and fully welcome in Oak Park.
Until her recent death, Raymond never hesitated in proclaiming the exceptionalism of Oak Park’s historic narrative. For the majoritarian community, she represented who we claimed to be, what we said we aspired to, and what we actually did right into the new millennium.
On her retirement in 1996, village and regional bankers, realtors, municipal officials, and voluntary groups posted statements of praise and gratitude in a 16-page supplement published by Wednesday Journal on July 31. The testimonials were a celebration of both Raymond and the proclaimed success of managed integration reflected in the vibrant, cosmopolitan, highly desirable community Oak Park had become with its ever-escalating housing prices and rents. For her admirers, Raymond was the keystone linking the racial stability and economic success that civic and business leaders had worked to achieve since 1968 (1).
A dedicated, relentless architect
Raymond was the central architect of the fundamental strategies for reversing or at least checking how the real estate industry fueled the decades-old racist practices of blockbusting and panic-peddling that contributed to massive white flight from Chicago neighborhoods on the West and South sides. Raymond, as much as any individual, worked directly with white and Black families and apartment owners to launch the first wave of integration in the late ’60s and early ’70s (2).
Raymond’s master’s degree study of housing segregation at Roosevelt University in the late ’60s concluded that white flight (in fear of Black residents) was not inevitable. She stressed that deliberate, preventive local government actions could check white flight while offering whites and Blacks the economic and social benefits of integration — the ideal espoused in the mainstream national and regional civil rights movement (3).
With others, Raymond proposed doable measures that were adopted in the ’70s when fears of Black migration to Oak Park peaked following passage of the federal Fair Housing Act (and Oak Park’s local ordinance) in 1968 and the 1973 Village Diversity Statement, passed by trustees, pledging to be a welcoming place for all.
With civic and religious allies, Raymond swayed Oak Park elites to back the creation of the Housing Center and make it the engine for managed integration and racial distribution moving forward (4).
The bold actions of Raymond were vital for convincing whites to remain in Oak Park while promoting the practical and idealistic goals of integrated living. In response, the national media heaped praise on the village and the OPHC. The immediate success of the village’s strategies brought thousands of whites and Blacks and many Asian Americans to the village, although thousands of whites also left in an out-migration process that continued through the ’80s (5).
Raymond the antagonist
Like archetypes in any community’s grand narrative, Raymond has been both praised and criticized. Over the years I interacted with her many times socially and politically. Our exchanges over school equity-centered policy issues were acrimonious. In the ’80s, education activists, including the leadership of courageous Black teachers, like Ella Pappademos and Betty Smitherman, moved beyond inter-school integration metrics to take up intra-school equity concerns, especially around ability grouping and curriculum tracking (6). Raymond was relentless in telling equity advocates to desist from challenging what education historians call “second generation segregation.” She authoritatively insisted that equity activists’ efforts would frighten away middle-class white families who were essential to the success of managed integration.
In the ’90s she rebuked similar efforts in District 200, led by African American Parents for Purposeful Leadership in Education (APPLE) in coalition with students, the NAACP, and the Oak Park Area Lesbian and Gay Alliance (7). Raymond even told Black leaders that the high school did not need APPLE, which was founded by Gerald Clay in District 97 in the 1980s and then brought to D200 by Wyanetta Johnson and other Black leaders (8).
The anchoring critique of Raymond and the OPHC was its central strategy of racial steering — convincing whites to move to neighborhoods with a higher percentage of Black residents and Blacks to move to neighborhoods that were mostly white. Critics for decades, including the 2024 citizens inquiry into reparative action for past racial harms (9), have rejected racial steering and the dispersal of Black residents. For them steering was as morally tainted and culturally harmful as the practices used by realtors and bankers in the past and still today to exclude Black and other racial minorities from white communities (10).
Years after she left the OPHC, Raymond, while acknowledging the tight legal line the Housing Center walked with steering, continued to defend its core strategy as morally sound. She defended it as affirmative steering, necessary for the greater good of racial integration. Still, from the ’80s into the 2000s the list of dissenters grew. It eventually included prominent and respected Oak Parkers like Sherlynn Reid, the retired and heralded head of the village’s Community Relations Department, local and regional NAACP leaders like Jaslin Salmon and William Simpson and D97 school board members.
Raymond, never naming her critics, dismissed these respected villagers as being uninformed on what it took to accomplish integration. She insisted they were naïve to believe that the strategies of racial steering and dispersal of the village’s Black residents and students were no longer needed (11).
Despite her critics and the alleged moral flaws of managed integration, Roberta Raymond remains the most significant individual in the prevailing narrative on Oak Park’s modern housing history (12).
*Sources can be found in the online version of this article at oakpark.com/Opinion.
John Duffy is an Oak Park resident, retired high school instructor, and a member of CEEE (Committee for Excellence and Equity in Education).
- David Murray. https://chicagoreader.com/news/the-gatekeeper-2
- Derrick Lewis. A whirlwind of change. Housing Center https://oprhc.org/2019/05/in-memoriam-of-bobbie-raymond/WednesdayJournal. Special supplement on Bobbie Raymond’s retirement, July 31, 1996.
- Doug Deuchler. A Conversation with Roberta Raymond, https://www.youtube.com/results?search_query=doug+deuchler+bobby+raymond, 2014.
- Carole Goodwin. The Oak Park Strategy: Community Control and Racial Change, 1979.
- Ibid., Deuchler.
- John Duffy. https://www.oakpark.com/2020/11/25/promise-and-challenge-of-managed-school-integration/
- John Duffy. https://www.oakpark.com/2020/12/16/the-volatile-80s-in-district-97/
- John Duffy. https://www.oakpark.com/2021/03/10/the-divisive-oprf-election-of-1995/
- Interviews. Burcy Hines, George Bailey, Henry Fulkerson, Dean Christ, 2026.
- Historical Harms to the Black Community of Oak Park and Suggested Repair, 2024,
- William Simpson, NAACP testimony at the U.S. Civil Rights Commission, 1986.
- Ibid, Murray; ibid, Deuchler.
- Ken Trainor. Oak Park’s fierce and feisty advocate, https://www.oakpark.com/2019/05/14/oak-parks-fierce-and-feisty-advocate.