After nearly four decades of public service in Wisconsin’s courts, Holly Szablewski will retire on December 30, concluding a career that spanned county and statewide leadership roles and supported court operations across the state.
Szablewski has been Deputy Director of State Courts for the Office of Court Operations since June 2023. In that role, she led the Court Operations team and worked closely with District Court Administrators to support circuit courts across Wisconsin.
Before joining the state office, Szablewski spent more than 35 years working in Milwaukee County’s justice system. From 2014 to 2023, she served as the District Court Administrator for the First Judicial District, overseeing court administration in Wisconsin’s largest judicial district. Earlier in her career, she spent 13 years as Milwaukee County’s Judicial Review Coordinator, where she managed the Court Coordinators Office and administered pretrial services, drug treatment court, and other court-based early intervention programs.
Szablewski began her professional career with Wisconsin Community Services, first as a volunteer in the agency’s pretrial screening program and later as an administrator overseeing several pretrial initiatives. That early work laid the foundation for a career focused on court operations, problem-solving courts, and collaboration across justice system partners.
Reflecting on her career, Szablewski expressed appreciation for the people she worked with throughout the court system. “I’m fortunate to have had such a long career in the courts working alongside so many talented, hard-working, and dedicated people,” she said. “I will miss that, but I am really looking forward to the next chapter of my life.”
Over the course of her career, Szablewski contributed to initiatives that supported court efficiency, strengthened administrative coordination, and expanded access to programs designed to address underlying issues in the justice system. Her work supported judges, court staff, and justice partners at both the local and state levels.
Szablewski said she looks forward to focusing on family, friends, and interests that bring her enjoyment, including time outdoors and photography.
Third Branch eNews is an online monthly newsletter of the Director of State Courts Office. If you are interested in contributing an article about your department’s programs or accomplishments, contact your department head. Information about judicial retirements and judicial obituaries may be submitted to: Sara.Foster@wicourts.gov