R.G. "Kelly" Caldwell, Jr.

R.G. "Kelly" Caldwell Jr.

President, Chief Executive Officer, and Chairman

R.G. “Kelly” Caldwell Jr. — president, CEO, and chairman of Caldwell Trust Company — began his career in 1988 after graduating with high honors in engineering from Georgia Institute of Technology. Although he originally planned to attend law school, Kelly joined his father’s firm, Caldwell & Co., gaining hands-on experience in investment advisory and trust services.

In 1993, Kelly and his father founded Caldwell Trust Company, one of Florida’s few independent trust companies, focusing on family trusts and highly personalized client service. By combining entrepreneurial vision with proprietary technology, the firm quickly established a competitive advantage that continues to distinguish it today.

Kelly became CEO in 2007 and has since led the company through a period of significant growth — increasing assets, income, and equity by more than 85% — while making substantial investments in technology and IT security. His leadership philosophy centers on long-term relationships and stewardship. As he explains, “Taking care of families is a primary mission here. We get to know each family, address their special needs, and ensure their wishes are fulfilled.”

In 2025, Kelly was honored as Trust Banker of the Year by the Florida Bankers Association — an award recognizing his outstanding contributions to the Florida trust and wealth management industry. 

A committed community leader, Kelly serves on the Florida Bankers Association’s Trust Executive Committee boards and is a board member of FCCI. He remains active with the Argus Foundation, where he was a two-term president, and recently retired from the Sarasota Sheriff’s Office Charitable Foundation and Suncoast Charities for Children. Kelly is also a proud alumnus of the Leadership Florida Class of XXVIII.

A licensed pilot, Kelly enjoys traveling with his wife, Melissa, and their three sons, Brooks, Zach, and Chase, as well as boating, diving, fishing, and tennis.

Caldwell Trust Company, with offices in Venice, Sarasota, and Vero Beach, manages over $2 billion in assets. The firm serves as trustee and trust manager for families, invests client assets across stocks, bonds, and other instruments, and provides retirement plan services for employers.