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Hon. Henry R. Simmons

Hon. Henry R. Simmons

Managing Partner
Chicago, Illinois

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 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. 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.

Judge Simmons (Ret.) previously served as a judge with a 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, 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 the damaging of US Route 66.

Prior to serving on the bench, Judge Simmons (Ret.) served as an Assistant Cook County State's Attorney. For 12 years, Judge Simmons (Ret.) 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 (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). The Cook County State's Attorneys' 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. Most recently, he will be honored in November, 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.) also gives back to the legal community in his speaking to various organization on a wide range of subjects. For example, 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). 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, Medical Malpractice and Litigation Update (moderator). Judge Simmons (Ret.) 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 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.

Areas of Practice

  • Medical Malpractice and Hospital Negligence
  • Personal Injury
  • Premises liability
  • Wrongful Death

Certified Legal Specialties

  • Mediation 40 hour Certification

Bar Admissions

  • Indiana, 1981
  • Illinois, 1980
  • U.S. District Court Northern District of Illinois, 1980
  • U.S. District Court Southern District of Indiana, 1981


  • DePaul University College of Law, Chicago, Illinois
    • Juris Doctor - 1980
  • Purdue University, West Lafayette, Indiana
    • B.S. - 1977
    • Major: Economics


  • Panelist, Judges Symposium/Settlement Negotiations a Law Bulletin Seminar Series, 2011 - Present
  • Moderator, The Business of Medical Malpractice Liability, CBA CLE September 2011, 2011 - Present
  • Lecturer, “Effective Defense Advocacy: Constructive Criticism from the Bench regarding the Use of Experts”, ADR Systems, 2011 - Present
  • Lecturer, “Motion Practice and Pre-Trial Settlements”, ADR Systems, 2011 - Present
  • Lecturer, “Winning at ADR: Understanding Advocacy in Arbitration and Mediation”, IICLE, 2011 - Present
  • Lecturer, “Negotiation, Mediation, Arbitration and Litigation”, ADR Systems, 2011 - Present

Honors and Awards

  • American Legion Award of Excellence Post #808
  • State’s Attorneys’ Recognition of Service Award
  • Appointed by the Illinois Supreme Court to the Committee on Illinois Pattern Jury Instructions in Criminal Case, 1994 - 2004

Professional Associations and Memberships

  • American Bar Association (ABA)
  • Chicago Bar Association (CBA), Member
  • Chicago Kent College of Law Extern Program, 2007 - 2011
  • Circuit Court Extern Program, 2007 - 2011
  • Illinois Judges Association (IJA), Member
  • Lawyers’ Assistance Program- Trained Intervener, 2010 - Present

Past Employment Positions

  • State of Illinois Circuit Court, Cook County Judicial Circuit, Circuit Court Judge, 1992 - 2011
  • Assistant States Attorney in Cook County, 1980 - 1992
  • ADR Systems of America, LLC, Senior Mediator & Arbitrator, 2011 - 2014

Pro Bono Activities

  • HighSight Organization volunteer, 2006-2008

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