Atty. Henry R. Simmons
The Honorable Henry R. Simmons (Ret.) is Managing Partner at Clifford Law Offices.
Profile Summary
About Henry R. Simmons at a glance
Henry R. Simmons is a personal injury attorney based in Chicago, Illinois, practicing at Clifford Law Offices. They have 46+ years of legal experience, licensed to practice since 1980. Admitted to practice in Illinois (1980) and Indiana (1981). Educated at DePaul University (—, 1980) and Purdue University (—, 1977). Recognitions include Best Lawyers in America — Personal Injury Litigation - Plaintiffs (2026), Best Lawyers in America — Awards: (2026), and Best Lawyers in America — "Judge of the Year" by the Lawyers' Assistance Program(LAP), 2014 (2026). Serands clients in Chicago, IL and the surrounding metropolitan area.
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About
The Honorable Henry R. Simmons (Ret.) is Managing Partner at Clifford Law Offices. He joined the firm in 2014 coming from ADR Systems of America, one of the top mediation services in the country, 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. His experience in personal injury and multi-party disputes serves him well in running the 20+ lawyer firm at Clifford Law Offices in Chicago. He is known throughout the Chicago area as a fair person, a man with a calm demeanor and a personality that resonates with people of all ages, races, income levels, ethnicities, and backgrounds. He continues to use his knowledge and experience in representing current clients in trial strategy, mediations and settlement conferences.
LEGAL EXPERIENCE
Judge Simmons (Ret.) previously served as a judge in both the Law Division and Criminal Division of the Cook County Circuit Court for nearly two decades. While in the Civil Division, he was known as a peacemaker who achieved an extraordinarily high rate of success in settling matters. He presided over numerous high-profile cases involving complex issues and multi-party disputes. He successfully resolved a long-standing products liability dispute between Fortune 500 companies resulting in a multi-million dollar settlement. His perseverance and practical insight also 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 the damaging of US Route 66.
Prior to serving on the bench, Judge Simmons (Ret.) served for 12 years as an Assistant Cook County State’s Attorney. He handled assignments in the Felony Trial Division, Juvenile Court, Felony Review, Appellate Division and the Consumer Fraud Unit where he served as a supervisor. He was a seasoned prosecutor, handling a variety of high-profile trials. He was well respected throughout the county for his competence and work ethic.
INVOLVEMENT IN THE LEGAL COMMUNITY
Over the years, Judge Simmons (Ret.) 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 receiving the American Legion Award of Excellence (Post #808). He received the Cook County State’s Attorneys’ Recognition of Service Award. He served 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. He was honored in 2014 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 his community in various legal disputes. He is active in his church and numerous charitable organizations throughout the state.
Judge Simmons (Ret.) is an active speaker within the legal community. He was part of a half-day-long program of Cook County Circuit Court judges in 2011 where he spoke on advocacy tips regarding pre-trial conduct in a “Judges’ Symposium – Advice from the Bench” that earned attendees continued legal education credit (CLE). 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 Processe
Judge Simmons (Ret.) moderates a panel titled “The Business of Medical Malpractice Liability”. Judge Simmons (Ret.) has served as a judge in numerous law school advocacy mock court competitions. 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 (Ret.) graduated from DePaul University College of Law and Purdue University where he earned a Bachelor of Science degree in economics. He was admitted as a member of the Illinois and Indiana state bar associations.
Clifford Law Offices is proud of Judge Simmons’ (Ret.) most distinguished career as a lawyer, a judge, a certified mediator in the Chicago area over the past 35 years, and now as Managing Partner at Clifford Law Offices.
Practice Areas Explained
Henry R. Simmons's Areas of Practice
Each practice area below reflects the types of cases Henry R. Simmons handles, with a brief overview of what that area of law covers.
Personal injury attorneys help accident victims recover compensation for medical bills, lost wages, and pain & suffering. Most work on contingency — no fee unless you win.
Henry R. Simmons is one of 264,852 personal injury attorneys indexed nationally. Browse personal injury attorneys in Illinois →
Jurisdictional Context
Why local counsel matters in Illinois
Practicing law in Illinois. Legal matters in Illinois are governed by state-specific rules of civil and criminal procedure, statutes of limitations, and substantive law. Cases originating in Chicago are typically filed in the local municipal court or the appropriate Illinois state district court, depending on subject matter and amount in controversy. An attorney licensed in Illinois brings working knowledge of local procedural deadlines, judicial practices in this andnue, and the substantive law that applies to cases brought here. Out-of-state attorneys generally cannot represent clients in Illinois courts without local counsel or pro hac vice admission.
Looking for additional Illinois attorneys? Browse all attorneys in Chicago or all attorneys in Illinois.
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