Gilfrey T. Gregory was born in Honolulu, Hawaii. He grew up in Harlem, New York, and Springfield, Massachusetts. At the age of 16, he was incarcerated for the first time in New York State and was one of the first juveniles tried as an adult. At the age of 22, he finally came back home. Three-time recidivist in other states, he received a Paralegal certification during his last incarceration. There, he was the chairman of the Family Awareness Program at MCI Norfolk where he learned his calling to help people understand the importance of self-improvement.
After developing a love for writing, he wrote, directed, and performed two plays at MCI Norfolk. Upon his release, he worked at Pioneer Valley Project as a Community Organizer/Civic Engagement. He continued his desire to help others and became a Youth Facilitator and Organizer for Brotherhood on the Move. Seeing the necessity in his community for help and guidance along the lines of re-entry, Project Last Stop was born, a local non-profit organization of which he is the Executive Director. He also obtained a Recovery Coach Certification and keeps advocating for the community in areas needed. As a man of accountability with a deep-seated desire to see justice he became a member of the Harriet Tubman Project.