Lafayette Gregg began his career as a prominent attorney in Fayetteville, Arkansas, after establishing his law practice following a period of teaching. He held various judicial positions, including serving as Chancellor of the Pulaski Chancery Court and as an associate justice of the Arkansas Supreme Court. Gregg was also deeply involved in educational advocacy, working to establish the Arkansas Industrial University and overseeing the construction of key buildings. His business acumen was demonstrated through his leadership of the Bank of Fayetteville and his role as chair of the Arkansas Banking Association. Throughout his career, Gregg maintained a steadfast commitment to public service and community development.

Lafayette Gregg's political identity is marked by an intriguing blend of loyalty to the Union during the Civil War and a commitment to Arkansas's economic and educational development. Gregg's strategic philosophy appears highly localized, as evidenced by his dedication to establishing the University of Arkansas and his advocacy for Arkansas's participation in the Columbian Exposition. His stance on education is equally distinctive, combining progressive efforts like donating land for a school for Black children with traditional roles as a professor of constitutional law. Gregg's approach reveals a calculated effort to balance regional interests with broader educational reforms, leaving one curious about the interplay between his Unionist principles and his local boosterism.