TALLAHASSEE, Fla.— The Florida Bankers Association (FBA) is pleased to announce that Roland “Kelly” Caldwell, Jr., CEO & President of Caldwell Trust Company, has received the Association’s 2025 Trust Banker of the Year Award. The announcement was made during the FBA’s 66th Annual Trust & Wealth Management Conference in Fort Lauderdale.
This honor is awarded to an individual who has distinguished themselves during the previous year with dedicated service to the FBA, and to the Florida trust and wealth management industry.
“Caldwell Trust Company was founded by Kelly’s father, the late Roland Caldwell, and received its charter from the State of Florida in 1993,” Trust Division Chair Carlos Batlle said. “When Roland retired in 2007, Kelly succeeded as CEO, continuing his father’s dream. Through his dedication to excellence and hard work, the company has continued to grow and thrive.”
“While Kelly’s business success is undeniable, his dedication to his community and his industry truly set him apart,” FBA President & CEO Kathy Kraninger said. “He consistently makes time to serve his local community and support others in the trust industry. The FBA, and the Florida trust industry, have benefited from Kelly’s service on our Trust Executive Committee Board, where he generously shared his time and knowledge.”
The FBA’s dedicated Trust & Wealth Management Division serves institutions providing clients with private banking, asset management, and trust banking services. The Division has an executive board, as well as active and involved legislative and education committees, that work to create value for its Trust & Wealth Management members and their clients, customers and communities throughout the state.
Other FBA award recipients included Stacey-Ann Williams, who received the Tinsley-Wells Honor Graduate Award; Rep. Vanessa Oliver and Sen. Lori Berman, who received Friend of the Industry Awards; and Susan Walker, who received the Trust Hall of Fame Award.
For more than six decades, bankers and industry friends have helped lead the FBA’s Trust Division. We are pleased to honor these awardees for their contributions to the Florida trust industry and Florida’s economic well-being.
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Through advocacy, education and engagement, the Florida Bankers Association (FBA) supports Florida bankers in better serving their customers and communities. Established in 1888, FBA today represents more than 150 banks of all sizes, and their dedicated 134,000+ employees, operating in the state of Florida.




