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Where Tradition Meets the Future®

Henderson Franklin Welcomes University of Miami Law Graduate Jack Flagg

Tort & Insurance Litigation Attorney Jack FlaggHenderson, Franklin, Starnes & Holt, P.A., is pleased to announce that John (“Jack”) Flagg has joined the firm as an associate in the Tort & Insurance Litigation Department after successfully completing his summer internship. He will handle insurance defense claims involving premises liability, automobile, and personal injury matters. Flagg shares,

“I am thrilled to be part of a firm that holds a prestigious reputation in the legal community. My journey into law, inspired by my father and fueled by my experiences, has led me to this moment. I am eager to contribute to our clients’ success and uphold the values of trust and open communication that are essential for effective representation.”

Flagg brings a deep passion for the field, which he developed through his academic pursuits and real-world experiences. A graduate of the University of Miami School of Law, he has been immersed in law from a young age, inspired by his father’s career in the legal industry. Flagg’s academic journey includes serving as an articles and comments editor for the University of Miami’s Business Law Review and his distinction of being consistently listed on the Dean’s list.

During his time in law school, Flagg honed his skills in civil litigation, with a particular focus on torts and business litigation. His experience as a legal intern at the Miami-Dade State Attorney’s Office has equipped him with valuable courtroom experience. William (“Bill”) Boltrek, a mentor and colleague at Henderson Franklin, shares,

“Jack’s dedication to the legal profession and skills make him a perfect fit for our Tort & Insurance Litigation Department. I have witnessed his development from a passionate intern to a competent attorney, and I am confident in his ability to deliver outstanding service for our clients.”

Flagg is a member of the Lee County Bar Association and its Young Lawyers Division. His educational background also includes a Bachelor of Arts from the University of Virginia. Flagg is based out of the firm’s Fort Myers office and may be reached at or by phone at 239-344-1181.

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