Born in Tampa in 1972, Gregory attended the United States Air Force Academy from 1990 to 1994, graduating with a B.S.

From 1997 to 2000, Gregory attended the University of Texas School of Law, graduating with a J.D., with honors.

[1] After his military work, Gregory practiced law in Sarasota and managed a small business with his wife, Erica.

[2] Gregory defeated Democrat Liv Coleman in the November 6, 2018 general election, winning 61.87% of the vote.

[4] In 2024, Gregory was hired as president of State College of Florida, Manatee-Sarasota.