Headshot of attorney John O'Toole

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Headshot of attorney John O'Toole

John M. O’Toole

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Mr. O'Toole is a litigation attorney focused on insurance breach of contract and "bad faith" actions on the part of insurance companies as well as injury and liability due to professional negligence caused by medical care providers such as doctors and hospitals and nursing homes inclusive of wrongful death actions. He has experience dealing with errors and omissions actions brought against lawyers, real estate and insurance brokers, accountants, and financial institutions and investment counselors. He knows well how insurance coverage can come into play in the instances of products and employment liability and property damage along with the new threat of "cyber/liability" after having spent 30 years in the insurance industry as an adjuster, underwriter, and, broker. He has a particular interest in reinsurance or insurance for insurance companies. Mr. O'Toole will take on a select number of immigration and criminal cases because of the importance he attaches to these practice areas based on our uniqueness as a country and rights and privileges afforded to all Americans. Mr. O'Toole is a graduate of West Point and former infantry officer with his last assignment being with the XVIII Airborne Corps located at Fort Bragg, NC. In addition to being a licensed Illinois attorney, Mr. O'Toole is a CPA (inactive) and has obtained Masters Degrees from DePaul University in both Accounting and Taxation. He is married to his wife Emma and has two children, Ryan and Maegan. Mr. O'Toole is a passionate White Sox fan, golfer, and, fisherman!

Bar Admissions

  • Illinois, 1988
  • U.S. Court of Appeals 7th Circuit, 2014

Professional Associations

  • American Bar Association, Member, 2013 to Present
  • Illinois Bar Association, Member, 2013 to Present
  • Chicago Bar Association, Member, 2013 to Present
  • Illinois CPA Society, Member, 1989 to Present

Current Employment Position

  • Sole Practitioner

Past Positions

  • AmWINS Brokerage of Illinois, Vice President, 1998 to 2013
  • Market Corporation, Product Manager, 1989 to 1998

Ancillary Businesses

  • Tax Practice including Offers in Compromise and Criminal Tax defense

Practice Areas

  • Insurance Breach of Contract and 'Bad Faith' actions
  • Medical Malpractice, Nursing Home, and Wrongful Death
  • Professional, Employment, and Products Liability
  • Criminal
  • Immigration


  • Loyola University Chicago School of Law, Chicago, Illinois
    • J.D.
  • United States Military Academy (West Point), West Point, New York
    • B.S.
    • Major: Engineering

Classes & Seminars

  • Directors and Officers Liability, PLUS, 1995 to 1996

Pro-Bono Activities

  • Knights of Columbus (Roman Catholic charitable organization), 2014 to Present

Representative Clients

  • Small businesses and individuals
  • Reinsurance companies and broker intermediaries