Judge Gerald Cleary was appointed to the bench from the 10th subcircuit by the Illinois Supreme Court in 2016 following a distinguished legal career and a search by a blue-ribbon screening panel headed by retired Illinois Supreme Court Justice Benjamin Miller. The 10th subcircuit (hyperlink to map) includes much of the Northwest side of Chicago and near Northwest suburbs, areas where Judge Cleary has been deeply involved in the community. Judge Cleary has been given positive evaluations by every bar association which evaluates judges.

Born and raised in the area, Judge Cleary is a graduate of the University of Illinois at Urbana-Champaign and Loyola University Chicago School of Law. He and his wife Pattie, who was raised in Edison Park and attended Resurrection High School, have been married for 25 years and have four children. They are members of St. Catherine LaBoure Catholic Church in Glenview and volunteer with numerous charitable and community organizations.

At the time of his appointment by the Illinois Supreme Court, Cleary had extensive trial experience resolving complex civil and commercial disputes related to businesses, aviation carriers, health care providers and insurance companies. He counseled clients on business growth, regulatory compliance, corporate governance and risk management of liability, employment and commercial claims to mitigate current and future risk.


  • Judge of the Circuit Court of Cook County, Chicago, Illinois;
    Nominated to circuit court judge by Illinois Supreme Court Justice Anne Burke after receiving the highest evaluation from her judicial evaluation committee. Re-nominated to circuit court judge by Illinois Supreme Court Justice Mary Jane Theis for a vacancy in the 10th judicial sub circuit.
    • Currently assigned to the Chancery Division that handles statutory and administrative reviews, temporary and permanent injunctions, declaratory judgments, mechanics liens and mortgage foreclosures.
    • Previously assigned to preside over jury and bench trials, motions and plea agreements for misdemeanor and petty offenses.
    • Received in depth training and insight regarding the evaluation and resolution of issues that come before the court.
  • Pappas O’Connor, Chicago, Illinois;
    Partner of law firm specializing in counseling Fortune 500 companies regarding litigation, commercial, employment, insurance and corporate issues and disputes.
    • Extensive trial experience litigating complex matters involving aviation and transportation, class actions, civil rights, insurance coverage, product and employer liability, commercial claims, general tort and punitive damage claims with exposures in excess of one million dollars. Successfully tried over twenty-five cases to a jury verdict and obtained excellent results in over one hundred mediations and arbitrations.
    • Counsels Fortune 500 corporations regarding insurance issues, contracts, employment, corporate governance and regulatory issues. Performs risk mitigation management by conducting proactive risk evaluations, use of contractual strategies to shift risk with enforceable indemnity clauses, insurance requirements and modifying work practices resulting in the reduction of risk.
    • Effective litigation manager, strategic thinker and proponent of non-traditional conflict resolution strategies saving clients over $15 million dollars. Research and identify industry trends to resolve present concerns and prevent future occurrences. Develop, initiate and conduct training seminars to educate clients on risk management, best practices and revenue enhancement.
  • SmithAmundsen, Chicago, Illinois;
    Founding partner of 150 member law firm specializing in counseling Fortune 500 companies regarding litigation, commercial claims, employment issues, professional liability, insurance and corporate issues and disputes.
    • Litigated and formulated successful defense strategies for many matters for disputes involving mass torts, aviation, trucking, professional liability, commercial, and general liability. First chair responsibility all cases handled from the initial analysis of liability and damages, discovery, dispositive motions through mediation, trial and appeal.
    • Created and leader of aviation litigation team, initiated and established contacts with the London insurance market, international air carriers and international aviation organizations.
    • Executive leader with a background in corporate management, finance, marketing, operations and strategic planning of startups and a law firm that has grown to over 120 attorneys that has yearly revenue exceeding $20 million dollars.
    • Manage, train and supervise a team of attorneys and support staff and leverage the use of associate attorneys to maximize margins and provide client cost savings.
  • Querrey & Harrow, Chicago, Illinois;
    Law firm specializing in insurance defense litigation representing insurance companies and their policy holders in the defense of automobile, premises liability and coverage claims.
    • As a first year associate, assumed the primary responsibility for over seventy-five litigated matters which necessitated the ability to learn all aspects of discovery and trial practice at an accelerated pace. One of the youngest attorneys to negotiate and conduct jury trials. Developed excellent personal and client development skills through the successful resolution of cases. Leveraged vast early trial experience to expand practice to more complex matters. Practice grew to encompass product liability, toxic torts and aviation claims.


Juris Doctor, cum laude
Loyola University Chicago, School of Law, Chicago, Illinois

Bachelor of Arts, Major – Political Science, Minor – Economics, cum laude
University of Illinois, Champaign, Illinois


Admitted to Illinois State Bar
Admitted to trial bar of the United States District Court for the Northern District of Illinois
Admitted to trial bar of the United States District Court for the Northern District of Indiana
Admitted to trial bar of the United States District Court for the Central District of Illinois
Admitted pro hac vice to the Indiana State Bar and the Wisconsin State Bar


Certified Mediator by the Illinois State Bar Association
Vice-chairman of the Aviation and Space Law Committee of the American Bar Association
Aviation Law and Trucking Law Committee of the Defense Research Institute
Certified Instructor for Continued Education for Insurance Adjusters, Texas Department of Insurance