Kent Cummings focuses his practice on the insurance industry, representing insurers, insureds and self-insureds in all aspects of insurance-related law. He works with companies to create effective risk management strategies, including traditional and non-traditional insurance programs. He advises clients interested in alternative risk transfer, including such options as captive insurance, and insurance through risk retention groups or risk purchasing groups.

Clients rely upon Mr. Cummings to assist them in compliance discussions with insurance regulators, in communications with regulators regarding asset valuation and other accounting issues, in asserting insurance and non-insurance claims in conservation, rehabilitation or liquidation proceedings, in purchasing assets of insolvent estates of insurance companies, and in corporate organizations and reorganizations.

As a litigator, Mr. Cummings has represented parties challenging the validity of insurance regulations, insurers defending claims from insureds, parties making claims against insurance companies, primary insurers seeking contribution from co-insurers, primary insurers involved in disputes with excess insurers, excess insurers involved in disputes with primary insurers.

Mr. Cummings has extensive reinsurance experience.  He has been involved in treaty drafting and commutations, as well as reinsurance audits and accounting disputes. In arbitrations, he has represented both ceding companies making claims against reinsurers, and reinsurers defending claims brought by cedents. Mr. Cummings’ experience includes one of the few jury trials nationwide involving a reinsurance claim.

Professional Background

Mr. Cummings has worked in the insurance industry, communicating with insurance regulators nationwide on behalf of a nontraditional insurance organization, interacting with legislators on passage of insurance legislation, and handling numerous aspects of internal corporate finance and governance.

He joined Hinshaw & Culbertson in February 1993. Among his professional affiliations, Mr. Cummings is a member of the Illinois State Bar Association and American Bar Association.

Honors & Awards

  • Member of the Leading Lawyers Network, where he was selected by his peers as a Leading Lawyer in the area of Insurance, Insurance Coverage & Reinsurance Law


  • “Emerging Issues in Arbitration: A Viable Alternative to Litigation?,” Blue Cross Blue Shield 42nd Annual Lawyers’ Conference, Glendale, Arizona, May 2008.
  • “The Courts Respond,” Hinshaw’s 2007 Insurance Services Symposium, Chicago, Illinois, May 2007.
  • “Captive Insurance Considerations,” Hinshaw’s 2006 Health Care Conference, “Current Issues Affecting Health System and Hospital Boards and Management,” Chicago, Illinois, September 2006.
  • “Coverage Counsel’s Report—Claim Handling Liability,” Hinshaw’s Breakfast Briefing series, Schaumburg, Illinois, March 2006.


"Attorney Liability Insurance,"  co-authored, chapter 14, Attorneys' Legal Liability, 2014 edition.

Hinshaw Publications


J.D., cum laude, Loyola University Chicago School of Law, 1993

B.A., University of Maine, 1987