Jessica O'Brien, JD

Director

Jessica O’Brien is a retired judge and former attorney known for her unwavering dedication to community service. As the first elected Filipino judge in the State of Illinois, Jessica’s career has been marked by significant achievements in the legal field. Her journey through the federal criminal justice system, from indictment and conviction to self-representation in her appeal, has inspired her to advocate for meaningful change.

Jessica’s personal experience with the challenges of employment discrimination has fueled her passion for reforming systems that keep re-entering citizens oppressed. She is dedicated to advocating for systemic changes that address the barriers faced by formerly incarcerated individuals, including occupational licensing. Her experiences have positioned her as a powerful advocate for legislative reform, determined to transform her insights into policies that uphold the United States Constitution and the principles of “equal justice for all.” Her first-hand understanding of the legal system’s complexities allows her to provide valuable recommendations for improving various aspects of the federal criminal justice system.

Jessica’s history of volunteer service is extensive and widely recognized. In 2012, she was honored with President Barack Obama’s Call to Service Award by the White House. Today, she continues her commitment to service by supporting leaders and members of various re-entry organizations across different states, sharing her experiences, talents, and skills. She also collaborates with a Baptist Church Chaplain to build a ministry focused on regular group prayers, mentorship, and the development of leadership skills within the re-entry support community.
Her participation in justice-involved care programs nationwide, particularly those centered on entrepreneurship and leadership development, has strengthened her advocacy for policy reforms. Jessica recently completed the Morehouse School of Medicine Summer Bridge program for the Justice Involved Care program and earned a Lean Sigma Yellow Belt certification. These programs have equipped her with valuable skills and reinforced her belief in American exceptionalism to improve the lives of those stigmatized and marginalized due to their convictions.

A defining moment in Jessica’s journey was the loss of a former colleague and, in recent years, women she met who were killed or died unexpectedly while reintegrating into their communities. These experiences inspired her to dedicate her time and energy to comforting individuals facing legal battles or re-entering their communities. By providing support to those who feel isolated and abandoned, Jessica reinforces her resolve to be part of the solution and continue her impactful work.

Jessica is dedicated to community projects that she began early in her career and supports leaders committed to reforming the criminal justice system. Her unique perspective, grounded in extensive experiences and unwavering dedication, makes her a powerful advocate and leader in the justice-involved care community.

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