Charles A. Wolfe
BA '85 (Political Science), Pi Kappa Alpha
CEO, Chiles Hospitality
Anna Maria, FL
Chuck graduated from Stetson University with a degree in Political Science. He was a member of Pi Kappa Alpha and was inducted in the Honor Society of Omicron Delta Kappa. During his time at Stetson, he also served as a Board Member for the Boy Scouts of America and was a Youth Board Member as the National Explorer President from 1981-1982. As an Eagle Scout, Chuck advocated for LGBTQ rights inside the Boy Scouts establishment over a 10-year span, including an appearance on CBS News “60 Minutes” for his segment “Boy Scouts: No Gays Allowed.”
Chuck first served as Deputy Campaign Manager for Harry Johnston for Governor race ending in 1986. He continued his career by becoming the Vice President at Woolbright Development and rose to become President at Trustee Management by the early 1990s. In 1992, Chuck took on the role of Director of External Affairs for Florida Governor Lawton Chiles, during which time Chuck led the operations for the Hurricane Andrew Relief Center as well as Executive Director of the Miami Financial Emergency Oversight Board for restructure to avoid the City of Miami’s bankruptcy. He attributes his ability to listen with the “art of compromise” to his time spent with Lawton. Following this role, he became Executive Vice President and Chief Operating Officer at American Legacy Foundation. As the first employee of the company, Chuck developed up to $1.8B tobacco settlement funds among many other changes affecting the future of health against the tobacco industry while reducing youth tobacco use. Afterwards, he created Wolfe Strategies and then joined Gay and Lesbian Victory Fund and Institute as President and CEO for the next 12 years in DC; a national PAC supporting LGBTQ candidates. While in this role, Chuck was hailed by OUT as Out100 in 2010 and Power50 in 2012, 2013 and 2014 for his work in getting LGBTQ leaders elected to public offices. Chuck then spent time as a Partner of Wolfe Kinkennon. In 2018, he joined Governor Chiles’ son, Ed Chiles as CEO of Chiles Hospitality (founded in 1979) in Anna Maria, FL.
Beachside Hospitality Group acquired Chiles Hospitality’s beachfront restaurants in the summer of 2024. Chuck remains at Chiles as the company shifts its focus toward the Gamble Creek Farms in Parrish, FL. The farm is embedded in sustainable farming on 26 acres, serving local markets and products to restaurants and vendors by implementing the “circular economy.” A prime example of this begins by organic planting, using the trimmings from the plants for composting, which feeds back into the planting. They also use shellfish shells, fish amino acid, biochar and worm casting to assist with fertilizer and building materials. Additionally, Chiles is also beginning a new partnership with Shogun Farms in Tampa with product lines of wild boar.
Among his notoriety, Chuck also received the Distinguished Alumni Award from Stetson University in 2017. Chuck was chair of the CAS Advisory Board from 2011 – 2015 and was elected to the Board of Trustees, serving from 2015 – 2023. Additionally, Chuck has served on the Board of Directors on the Association for Managers of Innovation and the Stonewall National Museum and Archives. Chuck was re-elected to serve on the Board of Trustees in July 2025.
In addition to supporting Stetson University, Chuck has contributed to the Gay and Lesbian Victory Fund and Leadership Institute and the Land Trust Alliance.
Chuck enjoys traveling, hiking and horseback riding in his free time.