Skip navigation

Hon. Henry R. Simmons

Hon. Henry R. Simmons (ret.)

Clifford Law Offices
Managing Partner


The Honorable Henry R. Simmons (retired) is Managing Partner at Clifford Law Offices in Chicago. He joined the firm in 2014 coming from ADR Systems of America where he served as a Senior Mediator and Arbitrator for three years. He also worked as a Special Master and Neutral Fact Finder for ADR Systems, one of the top mediation services in the country.

Judge Simmons previously served as a judge with the Cook County Circuit Court for nearly two decades, where he served on the bench in the Law Division as well as the Criminal Division. His experience on the bench was wide ranging, from personal injury, premises liability, and professional malpractice to employment discrimination, real estate and construction cases. He served as a felony trial judge, presiding over many types of cases involving the most serious types of crimes. While in the Civil Division, he was known on the bench as a peacemaker and someone who achieved an extraordinarily high rate of success in settling matters. His trial experience included numerous high-profile cases involving complex issues and multi-party disputes. He was successful in resolving a long-standing products liability dispute between Fortune 500 companies resulting a multi-million dollar settlement. In addition, his perseverance and practical insight resulted in a $40 million settlement between the State of Illinois and a mining company with issues involving negligence, punitive and compensatory damages relating to damage to US Route 66.

Prior to serving on the bench, Judge Simmons served as an Assistant Cook County State’s Attorney. For 12 years, Judge Simmons handled assignments in the Felony Trial Division, Juvenile Courts, Felony Review, Appellate Division and the Consumer Fraud Unit where he served as a supervisor. He became a seasoned litigator for the State’s Attorney’s Office handling a variety of high-profile trials. He was well respected throughout the county in courtrooms from the south side to the Daley Center, where his competence and work ethic were exemplary.

Over the years, Judge Simmons has become very active in the legal community as a member of several bar associations. He was appointed by the Illinois Supreme Court to serve on the Committee on Illinois Pattern Jury Instructions in Criminal Cases from 1994-2004. He has been recognized by several organizations for his work and his dedication to the profession including the receipt of the American Legion Award of Excellence (Post #808). The Cook County State’s Attorney’s Office’s Recognition of Service Award was bestowed upon him for his serving as a weekly volunteer for the HighSight Organization in Chicago that supports high school students in the area of academics and social support from 2006-2008. In November 2014, Judge Simmons will be honored as the Judge of the Year by the Lawyers’ Assistance Program (LAP) for his volunteer work with this organization that helps lawyers in need. Since he left the bench, he has provided extensive pro bono legal work in dispute resolution in his community. He is active in his church and numerous charitable organizations throughout the state.

Judge Simmons also gives back to the legal community by speaking to various organization on a wide range of subjects. For example, he was part of a half-day-long program for Cook County Circuit Court judges in 2011, where he spoke on tips for pre-trial conduct in a judges’ symposium, Advice from the Bench, that earned attendees continued legal education credit (CLE). In the past three years, he has taught the following accredited CLE courses at law firms in the Chicago area: Effective Defense Advocacy: Constructive Criticism from the Bench Regarding the Use of Experts, Motion Practice and Pre-Trial Settlements, Winning at ADR: Understanding Advocacy in Arbitration and Mediation, Negotiation, Mediation, Arbitration and Litigation: The ADR Spectrum of Processes, and Medical Malpractice and Litigation Update (moderator).

Judge Simmons has served as a judge in numerous law school advocacy mock court competitions as well. Throughout his judicial career, he was a participant in the law school externship programs involving DePaul University College of Law and IIT Chicago-Kent College of Law.

Judge Simmons graduated from DePaul University College of Law, Juris Doctor, and Purdue University where he earned a Bachelor of Science degree in economics. He is admitted as a member of the Illinois Bar Association and the Indiana Bar Association.

Contact Us


Apply Now!


Phone: 815-753-8595
Swen Parson Hall 151

General Information

Admissions Information: 815-753-8595
Swen Parson Hall 151

Other Questions: 815-753-1068
Swen Parson Hall 270

Request Information

Give to the College of Law

Law Library

Like, Join, and Follow us on

Facebook   Facebook Groups   Twitter  LinkedIn