Gresham Barrett graduated from The Citadel, The Military College of South Carolina in 1983 and served in the United States Army until 1987, achieving the rank of captain in the field artillery. He managed the family's furniture store and was elected to the South Carolina House of Representatives from 1996 to 2002, where he chaired the Ad Hoc Committee on Urban Growth and served on multiple other committees. Barrett announced his candidacy for Governor of South Carolina in 2009, competing in the Republican primary but ultimately losing the run-off election. Throughout his career, he has been active in community organizations, including the Westminster Rotary Club, Boy Scouts, and various local boards.

Gresham Barrett's political identity is marked by a blend of traditional conservative values with an unexpected advocacy for school choice, suggesting an ideologically agile approach. His military background and community involvement hint at a deeply rooted commitment to service, yet his legislative focus on education reveals a surprising willingness to challenge conventional educational paradigms. Barrett's active role in local organizations underscores a localized strategy, potentially driven by a desire to address specific regional needs. His political career, from state representative to gubernatorial candidate, showcases a calculated ambition to influence broader policy debates while maintaining strong community ties.