Regina A. Ripley

blank image Regina A. Ripley
10 S. Wacker Drive
21st Floor
Chicago, IL 60606, US

T: 312.585.1478 F: 312.585.1401
Regina has almost 20 years of coverage experience advising, litigating, and mediating disputes for insurers around the country and in various state, federal and appellate courts.

Regina's expertise includes analyzing coverage, finding creative solutions and resolving high-stakes disputes between policyholders, claimants, and insurers, including:

  • Additional Insured and Contractual Indemnity
  • Bad Faith, including bad faith set-ups in some of the worst venues in the United States
  • Commercial Crime and Fidelity
  • Commercial General Liability
  • Cyber Liability
  • Directors and Officers' Liability
  • Fiduciary
  • Law Enforcement Liability
  • Professional Liability
  • Umbrella and Excess policies, including allocation issues between multiple policy layers and Insurer v. Insurer disputes

Regina handles appeals, provides training for insurance companies, and assists with policy drafting. She regularly assists insurance companies in settling complex matters, including assisting in evaluating and settling difficult underlying disputes. She has a strong track record of success in dispositive motions and appeals, as well as representing her clients in all aspects through trial. She is adept at managing and handling high-stakes litigation and contentious discovery.


  • Chicago Bar Association
  • Claims and Litigation Management Alliance

Awards & Rankings

  • Named to Crain's 2018 Chicago's Notable Women Lawyers

Before Nicolaides

Before joining Nicolaides, Regina was a national partner in a top 50 Law360 firm.

Outside Nicolaides

Regina serves as Founder and President of OPRF Alliance Soccer, a non-profit and 501(c)(3) community organization, which is focused on providing travel soccer opportunities to communities and children that might not be able to afford travel soccer. In her spare time, she enjoys spending time with her four children, reading and volunteering in her community.

  • Defended insurers in state court coverage action concerning $60 million dispute over CGL coverage for environmental mass tort claims, which included claims of bad faith.
  • Defended insurer in coverage action over wrongful incarceration claim that included issues concerning law enforcement and umbrella policies, and assisted in negotiating favorable settlement.
  • Defended insurers in state court CGL coverage and bad faith action concerning $20 million coverage dispute involving mass-tort claims policies.
  • Defended insurers in state court in a multimillion-dollar coverage dispute concerning CGL policy where there are claims of bad faith and allegations that the insurers owe a duty to defend and indemnify. Obtained favorable settlement.
  • Obtained favorable court rulings and, ultimately, settlement in defending insurer in $20 million coverage dispute in state court arising out of alleged Ponzi scheme and employee dishonesty, including bad faith claims.
  • Obtained dismissal with prejudice for insurer in federal court action involving a multimillion-dollar fidelity claim, including bad faith allegations, arising from employee dishonesty at non-profit organization.
  • Obtained summary judgment for insurer in state-court coverage dispute concerning CGL coverage (defense and indemnity) for multimillion-dollar contractor dispute.
  • Defended insurer in state court coverage action and obtained favorable settlement with condominium association that sought defense under its Directors & Officers policy.
  • Obtained favorable settlement in federal court coverage dispute over multimillion-dollar fidelity claim arising from health insurance fraud and related employee-dishonesty claims.
  • Successfully used favorable discovery and dispositive-motion rulings to obtain settlement for insurers in a $60 million coverage dispute in federal court arising from a trading Ponzi scheme and allegations of employee dishonesty.
  • Represented domestic insurer as national coverage and monitoring counsel in connection with claims under D&O, E&O, umbrella, excess, and health care institutional professional liability and general liability policies.
  • Served as national coverage counsel for the London market  in connection with claims under professional liability policies and financial institution bonds.


  • Presenter, "Duty to Defend & Bad Faith; Core Principles, Practical Risks, and Outcomes," Warrenville, Illinois (April 2018)
  • Presenter, "Insurance-Bad Faith - The Imperfect Claim: Addressing Problems Effectively and Diplomatically," London, England (September 2017)
  • Presenter, "Basics of Duty to Defend and Duty to Settle," London, England (January 2017)
  • Presenter, "Defending the Imperfect Claim," Chicago Legal Education Conference (July 2016)
  • Presenter, "Risk Transfer," Milwaukee, Wisconsin (May 2015)
  • Presenter, "Duty to Defend in Illinois," Hoffman Estates, Illinois (May 2014)