Judge Jack Fleming (Ret.) brings decades of legal and judicial experience to DDV Law, Ltd.,
where his practice focuses on probate litigation, estate planning, trust administration, and
guardianship. A lifelong Chicagoan, Judge Fleming leverages his years on the bench to deliver
informed, pragmatic legal solutions—particularly in complex probate and fiduciary disputes.
While serving on the Cook County Circuit Court, Judge Fleming sat in the Probate Division,
where he presided over adult guardianship matters, contested wills, and trust disputes. Earlier in
his judicial tenure, he served in the Criminal and Municipal Divisions, conducting hundreds of
bench trials, more than 25 jury trials, and ruling on significant constitutional and evidentiary
issues. His broad judicial experience across civil and criminal matters makes him exceptionally
well-positioned to handle the procedural and substantive challenges of probate litigation.
Judge Fleming has also demonstrated a strong commitment to continuing legal education. He
completed advanced coursework through the National Judicial College, including Financial
Statements in the Courtroom, Advanced Civil Mediation, and Comprehensive Civil Mediation.
He is widely respected for his integrity, courtroom insight, and the measured, respectful approach
he brings to every case.
Illinois State
DePaul University College of Law, JD
Marquette University, BA
