After graduating from Kalamazoo College, where he served as Captain of the Men's Golf and Hockey Teams, Gregory attended Thomas M. Cooley Law School, graduating with honors and earning both, his JD and LLM, in the span of only 27 months.
After starting his legal career in the Tax, Business, and Estate Planning arenas, Gregory found his calling as a litigator and, from 2015 until 2026, proudly defended the men and women who dedicate their careers to public service on behalf of the City of Detroit.
During his tenure with the City, Gregory represented his clients against more than a half-billion dollars in potential liability, including multiple cases with seven, eight, and even nine figure exposure(s), across various practice areas including: 42 USC § 1983 (Civil Rights), Governmental Immunity, Wrongful Death, Premises Liability, and Catastrophic Auto Injury. Despite the exceedingly high stakes, Gregory achieved outright dismissals in more than 45% of his cases and favorable defense verdicts in 75% of those that did proceed to Trial. In those cases that resolved by way of settlement or arbitration, the City paid, on average, less than 9% of stated demands.
In 2026, Gregory made the jump to private practice, joining the Allen Law Group as a Senior Associate in the Firm's Civil Litigation Practice, expanding his focus areas to include Labor & Employment, Municipal, and Commercial Litigation.
Away from the office Gregory is involved with the National Kidney Foundation and American Cancer Society. Between 2015 and 2022, Gregory coached varsity hockey at Royal Oak High School and then University Liggett School, culminating in back-to-back Girls State Championships in 2021 and 2022. After hanging up his skates and coach's whistle, Gregory turned his attention to his two other passions, golf and downhill skiing. He and his wife reside in West Bloomfield, Michigan with their dog, Penny.
