Alyssa Gregory

Alyssa focuses her practice on complex commercial litigation and arbitration matters. She represents insurers and reinsurers in insurance and health care disputes and arbitrations. She also has experience representing a broad array of clients involved in general commercial litigation matters, class actions, and trade secret misappropriation disputes.

Alyssa’s clients include reinsurers, health insurers, manufacturing, and construction companies, as well as consumer product companies. She tries cases, obtains summary judgments, represents clients in high-stakes arbitrations, and navigates complex litigation and regulatory issues. Alyssa also regularly advises life insurance companies regarding contestability and rescission of life insurance policies.

• Secured a final award in an arbitration hearing for a U.S. reinsurer regarding a surety bond dispute.
• Obtained summary judgment in federal court for a manufacturing company against trade secret misappropriation-related claims and defended an appeal of the summary judgment.
• Obtained a state court verdict for a construction company at trial concerning a construction contract dispute and defended an appeal of the verdict.
• Arbitrated an $80 million provider dispute for a health insurer.
• Regularly represents health insurance companies in provider and member disputes brought in both arbitration and litigation, arising out of breach of contract, fraud, and a variety of other disputes.
• Arbitrated a $100 million dispute for a reinsurer concerning long-term care insurance.
• Represents life reinsurance companies in disputes regarding reinsurance treaty issues.

• Best Lawyers in America® Ones to Watch: Commercial Litigation (2026), Health Care Law (2026)
• Super Lawyers® Illinois Rising Star, Business Litigation (2023-2025)
• Volunteer of the Year, PAWS Chicago Professional Board (2023)