Hon. Jack Callahan, (Ret.) - ADR Systems

ADR Systems


Hon. Jack Callahan, (Ret.)

IllinoisNeutral Availability

After years as a sought-after trial and pre-trial judge in the Circuit Court of Cook County, Judge Callahan brings his enthusiasm, compassion and a broad base of experience in all aspects of the law to his practice as a senior mediator and arbitrator. Colleagues describe him as an even-tempered, fair and effective jurist who is well respected by both sides of the bench. His experience resolving a wide variety of personal injury and commercial cases is supplemented by his time as an accountant and tax consultant. Judge Callahan remains a hard-working neutral who easily relates to parties. When not helping to resolve cases, Judge Callahan can be found in the Chicagoland area, volunteering for adaptive athletics, which are competitive or recreational sports for individuals with disabilities.

Types of Cases Resolved

  • American Disability Act (ADA)
  • Auto Liability
  • Aviation
  • Bad Faith
  • Business Dissolution
  • Civil Rights
  • Class Action
  • Condominium Board Dispute
  • Construction
  • Construction Accidents
  • Construction Defect
  • Contract
  • Defamation
  • Discrimination
  • E-Discovery
  • Elder
  • Eminent Domain
  • Employment
  • Engineering
  • Environmental
  • Errors & Omissions (E&O)
  • Estates
  • Family Business
  • Federal Employers Liability Act
  • Fee Dispute
  • Fiduciary Duty
  • Finance
  • Franchise
  • Fraud
  • Government
  • Guardianship
  • Harassment
  • Insurance Coverage
  • Landlord-Tenant
  • Legal Malpractice
  • Lender Liability
  • Mass Torts
  • Mechanics Lien
  • Medical Malpractice
  • Non-Compete
  • Nursing Home
  • Partnership Dispute
  • Personal Injury
  • Premises Liability
  • Probate
  • Product Liability
  • Professional Malpractice
  • Property Damage
  • Re-Insurance
  • Real Estate
  • Restrictive Covenants
  • Retaliatory Discharge
  • Sexual Abuse
  • Sexual Harassment
  • Shareholder Dispute
  • Storm Damage
  • Subrogation
  • Tax
  • Temporary Restraining Order (TRO)
  • Toxic Tort
  • Trade Secrets
  • Trusts
  • Unfair Compensation
  • Uninsured & Underinsured Motorist Claims (UM&UIM)
  • Whistleblower
  • Wrongful Death
  • Wrongful Termination

ADR Experience and Qualifications

  • Since joining ADR Systems in 2022, Judge Callahan has served as a full-time mediator and arbitrator
  • 12-year judicial career serving as Law Division Judge in the Circuit Court of Cook County, Jury Trial, 2018-2022; Motion Call, 2013-2018; Probate Division, 2011-2013; Traffic Division, 2009-2011
  • 21-year legal career including Attorney, Sullivan, Hincks & Conway, business law and real estate, 1996-2009; Assistant Cook County State’s Attorney, including serving in the Felony Trial and Gang Crimes Divisions, 1989-1996; Tax Consultant, Price Waterhouse & Company, 1988-1989

Representative Cases

  • Auto Liability: pedestrian struck by truck crossing the street and suffered closed head injury which impacted daily activity and created work restrictions; case settled for $1.8 million
  • Auto Liability: settled hundreds of cases involving automobile and truck collisions
  • Contract: successfully mediated dispute between a suburban teachers’ union and suburban school district regarding COVID related school and work issues
  • Employment: resolved significant dispute between a large commercial insurance brokerage company and longtime broker; parties disagreed on commissions due and related separation obligations; case resolved with all parties in a confidential settlement
  • Legal Malpractice: Longtime franchisee was terminated from a contract without cause; allegations involved attorney representation involving certain claims that were disallowed
  • Medical Malpractice: alleged negligence related to obstructed bowel evaluation and treatment resulting in life-long bowel management; settled for $2 million
  • Premises Liability: settled hundreds of cases involving snow/ice and other liability issues
  • Wrongful Death: 5-year-old struck and instantly killed by a large piece of municipal equipment while crossing the street to enter school; settled for $5 million

Professional Activities and Awards

  • Adjunct Trial Advocacy Instructor, DePaul University College of Law
  • Board Member, Marist High School Board of Advisors
  • Board Member, Claddagh Foundation
  • Member, Chicago Bar Association
  • Former Board Member, Great Lakes Adaptive Sports Association
  • Former Board Member, Miami Project to Cure Paralysis
  • Licensed Illinois Real Estate Broker

Presentations and Publications

  • Panelist, “Jury Trials During Covid,” Annual Symposium with the Judges, Law Bulletin Seminars
  • Panelist, “Controlling and Leveraging Zoom to Improve Advocacy,” Law Bulletin Seminars
  • Panelist, “Helping You Help the Jury,” Annual Symposium with the Judges, Law Bulletin Seminars
  • Panelist, “Motion Call Procedural Pitfalls,” Annual Symposium with the Judges, Law Bulletin Seminars
  • Panelist, “Motion Practice Missteps: Judicial Perspectives about What Not to Do,” Law Bulletin Seminars
  • Panelist, “The Role of the Court-Appointed Legal Guardian of a Minor,” Chicago Bar Association


  • JD, Illinois Institute of Technology Chicago-Kent College of Law
  • BS, Accounting, Marquette University


  • Illinois State Bar
  • US District Court for the Northern District of Illinois


I was a sitting judge for over twelve years, practiced law for over twenty years and have been a mediator and arbitrator since 2022. Many attorneys have tried cases in my courtrooms or mediated cases with me.

The disclosures listed above will not affect my neutrality in this dispute.

Judge Burke successfully mediated a complicated case with little chance of being resolved.  He read every word of the parties' submissions, asked astute questions, and worked hard to find a path to resolution.  Judge Burke communicated with the parties themselves - so that they felt they were important participants in working toward resolution. The case I thought was never going to settle, settled.

Robert W. Smyth, Jr., Esq.Donohue Brown Mathewson & Smyth