Nick J. DiGiovanni

In property and casualty matters, Nick has extensive experience representing both cedents and reinsurers in disputes involving professional malpractice, asbestos and pollution claims and allocations, directors’ and officers’ liability, cybersecurity issues, breach of representations and warranties, “follow the fortunes” and “follow the settlements” clauses, late notice, bad faith claims, M&A disputes, and regulatory challenges under numerous state insurance laws.

In life and health matters, Nick has handled some of the industry’s most complex and consequential cases, including disputes involving yearly renewable term premiums, jumbo limit issues, actuarial disputes, misrepresentations, “vanishing premium” life insurance products, and agency issues involving managing general underwriters and third-party administrators.

Drawing on decades of experience, Nick offers clients a comprehensive, strategic approach to dispute resolution. He partners closely with clients to develop coordinated, practical business strategies and solutions to the increasingly sophisticated challenges facing the insurance and reinsurance industry.

Nick is recognized by Chambers and Who’s Who in Insurance, and has been named an Industry Thought Leader, reflecting his status as one the most accomplished insurance and reinsurance attorneys in the U.S.

• Represented a major health care insurer in collecting damages in a $300 million dispute in Texas regarding the sale of two HMOs. The issues included the valuation of reserves and application of actuarial and accounting principles as they relate to the health care industry.
• Defended the London market in connection with disputes involving a captive insurance company and more than $1.5 billion in environmental and health hazard claims. The case was litigated in the Supreme Court of Massachusetts, Northern District of New York, Supreme Court of Bermuda, and House of Lords in London.
• Represented a life reinsurance company in a case of first impression regarding YRT Treaty Rate increases, securing a rate increase valued at $245 million.
• Represented a large international reinsurer in collecting $45 million of amounts due under a quota share treaty reinsuring an Argentinian pension fund business.
• Prosecuted a case for a major U.S. reinsurance company with respect to claims of rescission on $40 million of retrocessional coverage relating to a small group medical quota share treaty.
• Defended a major U.S. life reinsurer in a $30 million dispute regarding a contract interpretation of recapture provisions.
• Represented an international property and casualty reinsurer concerning large catastrophe losses associated with Hurricane Katrina.
• Obtained a $12 million rescission judgment for a large international property and casualty reinsurer.
• Represented a large international insurer and reinsurer regarding an aggregation of COVID-19 related losses.
• Acted as national coordinating counsel for a large U.S. insurer with respect to workers’ compensation claims related to COVID-19.
• Represented a U.S. bond insurer in a $25 million dispute with the Department of Justice regarding immigration and bail bonds.
• Represented a large U.S. reinsurer regarding surety bond disputes.

• Lexology Index: Thought Leaders: Insurance and Reinsurance (formerly Who’s Who Legal) (2025)
• Chambers USA: Insurance: Dispute Resolution: Reinsurance, Illinois (2016-2025) and Nationwide (2025)
• Lexology Index: Global Elite Thought Leader, Insurance and Reinsurance (formerly Who’s Who Legal) (2023-2024)
• Best Lawyers in America®: Insurance Law (2006-2026) Reinsurance Law (2021-2026)
• The Legal 500 United States, Accomplishments in the Reinsurance Practice (2019)
• Best Lawyers in America®: Lawyer of the Year, Chicago Insurance Law (2016)
• Guide to the World’s Leading Experts, Insurance and Reinsurance (2013)
• Intelligent Insurer, The Legal Elite (2013)
• Best of the Best USA, Insurance and Reinsurance Practice (2009)