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The Way It’s Meant to Be

by Caldwell Trust

Driving around downtown Sarasota in the late 90s, R.G. “Kelly” Caldwell, Jr., owner of Caldwell Trust Company, spotted The Wilson Building at 27 S. Orange Avenue. He immediately thought it would be the perfect building for a future Caldwell Trust Company office. It was more than just a law office; it was a very stately building in a great location.

Through the years and as Caldwell Trust Company grew, Kelly started seriously looking at Sarasota office locations but kept coming back to The Wilson Building. At that time, Clyde Wilson, Jr. and Clyde Wilson, Sr. had purchased the building from the original builder and opened their law practice. The problem? The building was not for sale. 

Kelly and his team made several attempts to find other office locations knowing that Kelly’s ultimate desire was The Wilson Building. He continued to reach out to Clyde Wilson, Jr., and one meeting turned into many. During that time, Kelly explained to Clyde Wilson, Jr. his intent for the building, to retain and carry out a family legacy. That resonated with Clyde because his business started with his father. We believe that because the potential new owners of The Wilson Building would also be a family business, and the legacy of the building would continue, may have struck a chord with Clyde. He and Kelly negotiated for Caldwell Trust Company to purchase and preserve the structure at 27 S. Orange Avenue.

In renovating the building, Kelly preserved and enhanced what he could. He didn’t want to lose the building’s character and warmth. 

Caldwell Trust Company moved in at the end of May 2022 and held a grand opening on October 27, 2022. Over 500 people joined us that evening, including Clyde Wilson, Jr.

We did have a special surprise for Kelly, the man that made this incredible investment to restore and not build up. The Sheriff for Sarasota County spoke about the accomplishments of not just Caldwell Trust Company but specifically Kelly Caldwell’s commitment to the communities of Sarasota County. The Mayor of the City Commission then presented Kelly with the key to the city and thanked Kelly for how much he has done for the betterment of the city of Sarasota.

This building is representative of Caldwell in so many ways. It was never a thought to tear down the building. Preserving legacies is what we do. We’re a relationship business, so our clients, our company, is based on trust, it’s based on understanding, and it’s based on intent. The timing of moving into the building and hosting the grand opening aligns perfectly with the start of our 30th year. November 2023 will be 30 years in existence in Sarasota County – thirty years of delivering relationship-based services the way it’s meant to be.

Join R. G. “Kelly” Caldwell, Jr. of Caldwell Trust Company along with other historic groups as they present during History Day in the Park on Saturday, March 25, 2023. https://historydayinthepark.com/blog/

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