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Jessica Kirkwood Alley

A litigator at heart, Jessica Alley thrives in the world of complex litigation. Jessica enjoys working with clients to develop and execute just the right litigation strategy for the client's particular need. She is equally at ease whether she is working side-by-side with in-house counsel, or leading the charge herself for an individual client. Jessica has focused her career representing clients in the insurance, legal, and healthcare industries.

Jessica's extensive insurance experience includes defending insurance agencies, MGA's, surplus lines brokers, and insurance professionals from errors and omissions claims. In addition to defending professional liability claims, Jessica has represented these professionals in contractual disputes with carriers involving underwriting guideline compliance and indemnity disputes under agency management agreements. She's also provided counseling to insurers construing insurance policies and has litigated numerous declaratory judgment actions on behalf of domestic and foreign insurers. Jessica's comprehensive experience helps her to understand the industry from a unique perspective.

Jessica also has extensive experience representing attorneys and law firms in defense of legal malpractice claims. She also has considerable experience defending healthcare companies in high profile and high-stakes litigation asserted under the False Claims Act and other federal statutes.

Based in Tampa, Jessica represents clients throughout Florida and beyond. She has litigated cases in state and federal court as well as private arbitrations. Jessica is a Partner in the Litigation Practice Group and a member of the Firm's Insurance/Reinsurance Industry Team. Before joining Freeborn, Jessica was a partner at Phelps Dunbar LLP.


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