Gregory graduated from Morehouse College ('87) with a Bachelor of Arts in Journalism. After working several years as a journalist and investigative reporter, he entered law school at the University of Wisconsin ('94) and focused his studies on administrative law (labor and employment law, negotiations, constitutional law, arbitration, litigation, collective bargaining, contract, Litigating Before the NLRB, FLSA, Discrimination and Harassment, OSHA, private [NLRA] and public sector Labor [WERC, PERB] Law), and was a member of Wisconsin's Moot Court Team. After law school, he worked at a boutique labor and employment law firm (management-side) in Memphis for several years, and relocated to Milwaukee, Wisconsin, to work in the City's Attorney's office as an Employment and Labor Attorney, representing the City's Municipal Executives (Police Chief, Fire Chief, City Librarian, City's Labor Department, Hospital, City Engineer, Chief of Sanitation). Eventually, he secured a job as an Employment Attorney and Hearing Officer with the National Labor Relations Board (NLRB), where he worked almost twenty years. Most recently, he worked as the Principal Labor Relations Representative for the County of Santa Clara in California. He currently teaches at Ohio Christian University (William Seymour College).

He earned his Master of Divinity from Regent University (2014), focusing on Executive Coaching, Life Coaching, and Practical Theology. Also, Gregory has earned a Master of Fine Arts in Creative Writing from the University of Alabama ('04), focusing on writing plays and poetry; his first collection of poetry, Tin Ears {Bowie, Maryland: Broad Wing Press, 2016 (ISBN 1-938373-07-3)} was recently published. Also, he is currently writing a cycle of 7 plays that address racial reconciliation, Voting Rights, Civil Rights, Religion, Union, Convict Leasing, Works Songs, and Blues.The first play, Ruby's Harmonicas & Pianos, Incorporated, was premiered by the Aldridge Theatre Company at the Downtown Theatre (Birmingham, Alabama) on 17 April 2016. He has completed two additional plays in the cycle (Beans Bones Blues and No Honey in the Rock); he is currently writing a fourth play, Leviâ??s Processing & Packaging, Incorporated, and recently started researching the fifth play in the cycle, Fire in My Bones, which addresses the genesis of the Student Nonviolent Coordinating Committee.