Credit: By David Dahmer Madison 365
Jerome Dillard has dedicated his life’s work to opening doors for others and supporting individuals as they transition into the community after incarceration, and now that community wants to celebrate the life and legacy of the longtime executive director of EX-incarcerated People Organizing (EXPO) of Wisconsin with a special retirement celebration on Friday, Dec. 12, at the Black Business Hub on Madison’s South Side.
Dillard leads EXPO of Wisconsin, a statewide, peer-led movement that focuses on reentry, justice, and community healing for former prisoners upon their release from institutions. Friday night will be a special night to celebrate and honor the retiring Dillard, who is a revered figure in the reentry community.
“This is an invitation to the community, to anyone who has been touched by Jerome …. and we know, myself included, that he has just made such an impact for so long for those of us that, quite frankly, everyone else turned away from … but he didn’t,” Marianne Oleson, the operations director at EXPO of Wisconsin, tells Madison365. “To so many people, he said, ‘You mattered. You deserve a shot.’ He literally saved my life twice.”
Dillard is responsible for building, along with formerly incarcerated leaders, EXPO of Wisconsin, a non-profit that provides housing, workforce development, recovery, peer support, and civic engagement. Dillard has dedicated over two decades to reentry work, supporting hundreds of individuals during their transitions into and out of the community before and after incarceration.
In previous roles, Dillard worked as the Dane County re-entry coordinator, where he created the Transition from Jail to Community (TJC) model for Dane County, helping reintegrate individuals from jail to the community. Dillard has also served as a resource specialist for Madison area Urban Ministry (now JustDane), the chair of Voices Beyond Bars, and the director of Re-entry and Advocacy Services for Nehemiah.
Jerome Dillard with Cornel West
Dillard also worked as the human services program coordinator/recovery support specialist at Wisconsin Resource Center, a maximum-security mental health and AODA prison operated by the Department of Health Services Division of Mental Health and Substance Abuse Services (DMHSAS).
“Jerome’s retirement party is a great chance for people in the community to come and see him and wish him the best,” Oleson says. “His lifetime work is amazing. Jerome had the understanding that punishment only compounds the harm.”
Dillard’s retirement party will take place on the fourth floor of the Black Business Hub in the screening room, the kitchen, and the lounge area. There will be drinks and appetizers, a short program and open mic tributes to Dillard. “We’re going to be running a slide show of photos and articles of Jerome through the years. We will have hors d’oeuvres. House of Flavas will be catering,” Oleson says.
Dillard has earned numerous accolades and awards for his contributions in re-entry work, including the 2008 City/County Martin Luther King Jr. Humanitarian Award. Dillard’s dedication to expanding health equity was recently recognized by the Wisconsin Public Health Association, which honored EXPO with the Expanding Health Equity Organizational Award.
To RSVP for the event, e-mail info@expowisconsin.org
“We are really excited about this. It’s going to be a phenomenal event,” Oleson says. “It’s just an opportunity to come and let Jerome see and feel the impact he’s had on this state and on this community for decades.”
Dec 10, 2025
