Gregory was born in Wilmington, Delaware, and raised in Oxford, Pennsylvania. Gregory attended the Oxford area school district where he graduated.
Gregory joined the Union Fire Company where he currently is an Honorary Active member. He obtained his Emergency Medical Technician and went on to be employed with Southern Medical Emergency Services. While working for SCCEMS, Gregory attended the Police Academy. After completing the Police Academy, Gregory graduated and became employed with the Chester County Sheriff’s Office.
Gregory then accepted a job with Cecil County Sheriff’s Office, where was employed for 20 plus years. Gregory retired from the sheriff’s office on March 1, 2022, leading to his journey with R.T. Foard Funeral Home.