Major Gregory was born and raised in the Philadelphia area. He served in the United States Air Force from 1981 to 1985. He began his law enforcement career with the Pasco County Sheriff’s Office in 1990. He worked road patrol and was one of the initial members of the Community Oriented Policing Unit.
In 1993, he was transferred to the Vice and Narcotics unit and remained in the unit as a detective until being promoted to Sergeant in 1998. He remained in Vice and Narcotics until 2005 as a sergeant until his transfer to Property Crimes.
In 2010, he was promoted to Lieutenant and transferred to District 1 Patrol and took on additional assignments with the Motor and Step Units.
In 2013, he was transferred back to Vice and Narcotics as a Lieutenant and served a total of 18 years in criminal investigations.
In 2014, he was promoted to Captain and transferred to District 2 Patrol. During his career, he was also an adjunct instructor for the Institute of Police Technology and Management at the University of North Florida, teaching undercover techniques around the country. He has a bachelor’s degree in Criminal Justice from St. Leo University.
He has been married for 30 years and has 2 grandchildren. His oldest son is serving in the United States Army. In his off time he enjoys hockey, restoring vehicles and riding motorcycles.