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Representative Tommy Gregory

United States Air Force Retired

Lieutenant Colonel

Representative Tommy Gregory is a native Floridian who served in the Air Force for 20 years and achieved the rank of Lieutenant Colonel before retiring in 2014. He began his military career by earning a B.S. in Economics from the U.S. Air Force Academy, where he graduated with Military Distinction. He also deployed to Southwest Asia for Operations Southern Watch, Iraqi Freedom, and Enduring Freedom.

Rep. Gregory received his J.D., with honors, from the University of Texas School of Law and served as a prosecutor for 14 in the U.S. Air Force Judge Advocate General’s Corps. His career included:


  • Serving as staff judge advocate for the 48th Fighter Wing in England. He supervised a 35-person legal office; oversaw the provision of legal services to 15,000 personnel, the drafting of 6,000 estate planning documents, and prepared 3,500 tax returns; and managed the pre-trial advice, prosecution, and appellate review of 50 felony and 270 misdemeanor cases.

  • Serving as a Senior Counsel for the Air Force Space Command legal office in Colorado, where he managed the daily operations of a 15-person office and oversaw the delivery of 4,200 legal opinions to a four-star commander and headquarters staff, as well as the review of all administrative law issues for ten legal offices around the country.

After retiring from the military, Rep. Gregory spent ten months doing missionary work in the Dominican Republic as his house was built in Sarasota. He then established a successful private law practice in Sarasota. He is currently with the Williams Parker Law Firm, where he focuses on litigation and advising clients, commanders, and senior leaders in high-profile, high-pressure situations.

The Representative has served on the boards of Habitat for Humanity Sarasota, St. Martha Catholic School, and the Sarasota Republican Club. His wife, Erica, is also an Air Force retired Lieutenant Colonel and a small business owner. They are raising three sons.

Rep. Gregory states, “I consider it a great honor to have served our country in Operations Iraqi Freedom and Enduring Freedom.” He goes on how his military career helps him in the Florida House, “During my career in the Air Force, I was taught and used a decision-making process called the OODA loop — OODA being an acronym for Observe, Orient, Decide, Act. This four-step approach to decision-making focuses on rapidly gathering information, putting it in the historical and current context, deciding appropriate actions, and then executing. It is a powerful tool for quickly zeroing in on the best answer to complicated questions and then repeating the steps as the situation changes. OODA can be applied outside the military.” Florida lawmakers are fortunate to have this military experience help shape policymaking in Tallahassee.

Tommy Gregory
air force
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