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 draws on his extensive experience on the bench to provide clients with informed, practical legal guidance, particularly in complex probate and fiduciary matters.
During his service on the Cook County Circuit Court, Judge Fleming served in the Probate Division, where he presided over adult guardianship proceedings, contested wills, trust disputes, and other complex probate matters. His time on the probate bench provided him with extensive insight into the legal and procedural issues that can arise when families, fiduciaries, and beneficiaries face contested estate and trust matters.
Earlier in his judicial career, Judge Fleming served in the Criminal and Municipal Divisions of the Cook County Circuit Court. During that time, he conducted hundreds of bench trials and more than 25 jury trials and ruled on significant constitutional and evidentiary issues.
His broad judicial experience across probate, civil, and criminal matters provides him with a unique perspective when advising clients and litigating complex legal disputes. He understands the procedural demands of the courtroom as well as the practical considerations that can affect the resolution of probate and fiduciary matters.
Judge Fleming’s practice at DDV Law focuses on matters involving probate litigation, estate planning, trust administration, and guardianship. His experience on the probate bench allows him to approach these matters with a thorough understanding of the issues facing courts, fiduciaries, beneficiaries, and families.
Whether addressing a contested estate, trust dispute, guardianship matter, or other fiduciary issue, Judge Fleming brings a measured and analytical approach to each case. His goal is to provide clients with clear legal guidance and practical strategies for navigating complex matters.
Judge Fleming has maintained a strong commitment to continuing legal education throughout his career. He has completed advanced coursework through the National Judicial College, including:
Judge Fleming has also been a frequent presenter on probate issues at continuing legal education (CLE) seminars, sharing his extensive knowledge and practical courtroom experience with fellow legal professionals.
His continued involvement in legal education reflects his commitment to staying informed about the legal, financial, and dispute-resolution issues that affect his clients and the broader legal community.
Judge Fleming is widely respected for his integrity, courtroom insight, and measured approach to the practice of law. He brings the perspective of a former judge to every matter while maintaining a thoughtful and respectful approach to clients, opposing counsel, and the courts.
DePaul University College of Law — J.D.
Marquette University — B.A.
