Leonard lair ing Westwood, New Jersey, putera saking Joyce Patricia (née Peterson), setunggalipun juru rawat, lan Robert Leonard, nggih punika guru ing Collier High School. Piyambakipun manggèn wonten Ridgewood, nglampahi sekolah wonten Ridgewood High School lajeng kuliyah wonten ing Fordham University lan Columbia University School of General Studies.