Thomas E. Shepard, Esquire

Associate Attorney

Thomas E. Shepard, Esquire

Thomas E. Shepard, Esquire

Associate Attorney

Thomas E. Shepard is an Associate at Boyle, Leonard & Anderson, P.A. and works in our Fort Myers office. Mr. Shepard was born in Chicago, IL, but grew up in Durham, NC. He attended Northeastern University in Boston, MA for his undergraduate degree. While at Northeastern he served as Chairman of the Student Conduct Board. Following graduation, he returned home to North Carolina to attend law school at the University of North Carolina at Chapel Hill. While in law school Mr. Shepard worked as a law clerk, first for the North Carolina Center for Actual Innocence, and then the North Carolina Department of Justice’s Insurance Section.

Prior to joining Boyle, Leonard, & Anderson, P.A., Mr. Shepard spent a couple of years litigating Proposition 65 matters in California, which is similar in nature to class-action toxic tort litigation. In 2019, he relocated to Florida, subsequently joining Boyle, Leonard & Anderson, P.A. Mr. Shepard is an avid fan of the Carolina Hurricanes, Formula 1, and the New England Patriots. While away from the office, he enjoys golf, sporting clays, and boating.

Mr. Shepard’s practice is primarily focused on appeals and insurance coverage disputes. As a result of the time he spent on Northeastern’s Student Conduct Board, Mr. Shepard is also passionate about protecting the individual rights to freedom of speech and due process of students in higher education. In furtherance of that goal he is a member of the Foundation for Individual Rights and Expression’s (FIRE) Legal Network, which provides counsel to students and faculty members whose rights are being threatened. He has also taken on pro bono representation of children who required counsel to protect their rights and interests and intends to continue to do so now that he has relocated to Florida.


  • Bachelor of Science, Political Science—Northeastern University, cum laude, 2013
  • Juris Doctor—University of North Carolina at Chapel Hill, School of Law, 2016

Admissions to Practice

  • State of Florida
  • State of North Carolina
  • United States Court of Appeals for the Eleventh Circuit
  • United States District Court for the Northern District of Florida
  • United States District Court for the Middle District of Florida
  • United States District Court for the Southern District of Florida

Employment History

  • Chanler Group
    • Associate Attorney
  • North Carolina Department of Justice
    • Law Clerk
  • North Carolina Center on Actual Innocence
    • Law Clerk

Bar Memberships

  • The Florida Bar
  • Lee County Bar Association
  • Collier County Bar Association

Our Practice Areas of Expertise

Insurance Disputes and Claims

Insurance Bad Faith Claims

Insurance Coverage Co-Counsel

Insurance Agent & Insurance Broker Claims


Real Estate Matters

Mediation / Arbitration

Personal & Business Disputes

With offices in Fort Myers, Tampa and South Carolina, Boyle, Leonard & Anderson, P.A.
is an insurance litigation law firm that serves clients across North America and the Caribbean.

PH: 239-337-1303 | FAX: 239-337-7674

1501 W. Cleveland St., Ste 302
TAMPA, FL 33606
PH: 813-305-3019 | FAX: 239-337-7674

P.O. BOX 31578
PH: 854-800-0804 | FAX: 239-337-7674