TOM CUNNINGHAM leads the firm’s Privacy and Cybersecurity practice in Chicago. He is a trial lawyer who has first chaired over 25 trials and arbitrations and secured judgments and achieved settlements totaling over US$1 billion. Tom’s practice focuses on contested matters and regulatory enforcement proceedings over cybersecurity, privacy, insurance, and financial services-related issues. In addition to his contested work, Tom advises clients on digital risk management and compliance programs and conducts diligence in the corporate transactional context, based on his 30 years of representing clients in the US, UK, EU, and Bermuda in contested matters. He is also a Certified Information Privacy Professional/United States (CIPP/US).
Tom helps his clients achieve successful outcomes in complex, multi-faceted contested matters. For one publicly traded client, he orchestrated an internal investigation of corporate governance and securities regulation practices while overseeing the defense of an SEC enforcement action and a simultaneous shareholder activist campaign, all while coordinating strategy for and messaging with state insurance departments, credit rating agencies, and the public. For one insurance client, Tom defended against a series of multi-state insurance conduct and market examinations, developed the theory for and first-chaired the lawsuit against the lead agency for exceeding its authority, and secured an advantageous settlement of all outstanding matters.
Clients turn to Tom to navigate high-stakes cybersecurity and privacy matters, including data breach response and the resulting litigation and governmental inquiries that often follow. He has first-chaired the defense of class action privacy lawsuits and advised on regulatory investigations conducted by the New York Department of Financial Services and numerous other agencies. Drawing on his experience in contested cybersecurity matters, Tom helped develop the first ever 144A cyber risk catastrophe bond, for which the firm won the 2024 “Cyber ILS Award” from Insurance Insider.
Tom has advised clients in the development of cybersecurity and data privacy programs and counseled clients on CAN-SPAM, CCPA, FCPA, GDPR, HIPAA, UDAP, and state privacy laws. Tom advises clients on preparation for sophisticated cybersecurity incidents, including on development of policies and presentation of trainings and tabletop exercises. In his diligence work, Tom has advised clients on data privacy and cybersecurity issues for transactions across a host of industries, with particularly emphasis on insurance and financial services companies.
Tom also regularly represents companies in insurance-related disputes. He leads the firm’s reinsurance dispute practice and represents clients in life, health, property, casualty, and agent-related disputes. He has first-chaired trials and arbitrations over alternative risk transactions, Affordable Care Act reimbursements, asbestos, catastrophe bonds, COVID-19, commutations, environmental pollution, long term care, opioids, PFAS, talcum powder, wildfires, and yearly renewable term (YRT) premium increases. Tom is repeatedly asked to take over cases heading to trial from prior counsel.
Tom’s advocacy has earned him recognition in both Illinois and Nationwide by Chambers USA (2011–2025) for Insurance Dispute Resolution: Reinsurance. Clients in the 2025 edition of Chambers USA lauded Tom as “one of the leading counsel for coverage trials” with a “wealth of experience.”