Beyond the Bio

Getting to Know Dick Caldwell Outside the Courtroom

Getting to Know Dick Caldwell Outside the Courtroom

In this final installment of a three-part series, Dick Caldwell talks about lessons learned in the military as a young man and the things he loves, his family, photography and music.

Growing up in a small town in South Georgia, Dick Caldwell said it was easy to leave behind when he headed to the University of Florida for college. At the time, many Land-Grant Colleges required two years of ROTC training by male students. “If you wanted, you could select advanced ROTC for your junior and senior years along with a 6-week summer camp, which was a modified basic training regimen. It was a real pain in the neck at the time, but I’m glad I went through it because I came out an officer,” he continued.

When Dick graduated, he served in the 4th Armored Division Artillery, stationed near Nuremberg, Germany where he served as a captain, operations and training officer for the 2nd Battalion, 16th Artillery from 1965 until 1968 working on the Honest John rocket. “It was really just luck that kept me there during the Vietnam build-up,” he remembered.

Dick and his first wife Jo Ann, whom he met during his senior year in college, were married in Germany. “It was a delightful place to be and we were able to rent an apartment in town for several months before we had to move into officer’s quarters on the base,” recalled Dick.

“We spent our honeymoon in Munich and when we returned a week later, many of the people I knew had gotten orders to go directly to Vietnam and were gone,” he said. “You just had to live with the idea that any day you could get orders and have to leave. People in the military live with the notion of doing whatever you’re asked to do,” he explained.

Dick says he matured very quickly during that time because his military responsibilities increased rapidly. “The duty was difficult because we were short-handed most of the time and people were getting orders and being shipped out. I learned to be flexible and accept and adapt to the situation at hand. At just 22 years old, I was working with equipment worth millions of dollars and taking care of the soldiers under my command. I had to make sure my soldiers had adequate support and medical care as well as be ready to correct them if they did something wrong,” he said.

“In the Army, I learned to be committed to doing what needed to be done and to take things seriously. I’m not sure I had learned that when I graduated from undergraduate school, but I certainly did during my time in service.” 

As a father and husband, Dick started thinking more seriously about what he needed to do to support the family and applied to law school while he was still in Germany.

“By the time I got out, I was accepted into law school and headed to Gainesville. I worked at Sears delivering orders that first summer and had a lot of part-time jobs throughout law school. I did anything to help pay the bills,” he said. His wife worked as an elementary school teacher.

Dick and Jo Ann were married until she passed away in 1997. They raised their two children, a daughter and son, and Dick now has 5 grandchildren.

It can be said that Dick’s willingness to work hard is a large part of his success. “You must do the best you can for your client. If you aren’t giving your absolute best effort, than you aren’t fulfilling your responsibility,” he said.

Perhaps this grit and willingness to work hard comes from the military background or perhaps its innate within. Either way, that drive to outwork the other side is what Dick says wins cases. He spent a career building a practice and law firm with his partners Thom Rumberger and Bud Kirk (see part I and part II of this series).

Dick married Gloria Matyszyk in 2004 and together they share their passion of photography, travel and the arts. “Photography has been a great hobby,” said Dick. “When we met, we were both interested in photography and have enhanced our interest since then.”

Over the years, Dick and Gloria kept getting better cameras and equipment and their work kept getting better, too.

The Gathering,” shows birds feeding in a marshy area near Ft. Pierce, FL.

Whether at a local park or overseas, Dick enjoys getting out to take photos. “It’s gratifying to see different things and to try to memorialize them in a way that means something, at least to me. The creative process itself is enjoyable, particularly when a captured image really reflects the beauty of the subject, or at least captures the essence of it,” he explained.  

“The world of digital photography has given me a lot more artistic freedom.  I don’t have to invest in a dark room with equipment and chemicals. It’s much quicker and easier. When we were using film, you’d take a shot and that was a quarter, four shots, throw a dollar at it. With digital photography, I can take 100 shots and if I don’t like 98 of them, I just delete them.”

Their focus is outdoor wildlife and landscapes. “Gloria says, if it moves, we shoot. If it doesn’t, we shoot,” laughed Dick. “We have a lot of fun and it’s something we can do together. She’s a better photographer than I am, and we actually sell some of our work, but more for enjoyment than anything else,” he added. Their website,, is filled with beautiful photographs.

Dick and Gloria have been able to marry their love of photography with their love of travel. They’ve been to some amazing destinations—all seven continents, including Antarctica. At the time of this article, they had just returned from Yellowstone National Park. Dick spent time in March in South Florida with a professional photographer who took a group to Ft. Meyers to photograph birds in the Western Everglades. This photo is of “Mormon Barns” near Jackson WY, with the Grand Teton Mountain Range in the background.

“We travel wherever we get an opportunity. For instance, my daughter-in-law is from Australia, so we had a chance to go there and then last summer, I went to Switzerland for the Federation of Defense and Corporate Counsel annual meeting where I presented a paper,” he explained. “It was a marvelous opportunity to take pictures. It’s a beautiful country.”

Dick talked about their trip to Antarctica, which was about nine years ago. “We went with a National Geographic Expedition on a small ship. The large cruise ships go by, but there can only be about 100 people on land at a time, so they don’t stop,” he explained. “We went on shore two times a day. It was just amazing and the weather was beautiful,” he continued.

The trip was in January, which is mid-summer and the temperature ranged from 30-35 degrees Fahrenheit. Thanks to sunshine and no humidity, Dick said he wasn’t cold until he was back on the ship and moving. 

“We took some incredible photographs of the penguins, seals and landscape. There is a lot of contrast between the glacier, which is white but has a lot of rough terrain, the water, which is dark and the blue sky,” he said.

It is not surprising that Dick would find learning how to adapt to various lighting conditions fun and interesting. His curiosity and love of learning that serve him so well on his cases also serves him well in his chosen hobby.

“You have to learn to adapt to lighting conditions and what you’re shooting,” he said. “We’ve been to several programs and workshops and considering the light conditions is one thing they always focus on,” noted Dick.

Dick and Gloria are planning their next big trip for Iceland. “We had talked about going for about five years before we finally made it two years ago. It was just wonderful. We enjoyed it so much, we’re trying to get back there next summer.

One of Dick’s favorite places to photograph is the beach. He says he has loved the beach ever since he was old enough to remember. “My grandparents lived near the beach in the Panhandle, so we’d vacation there every year. Of course, I’d never want to go home. I have very pleasant memories of those times and the beach has always been a constant source of enjoyment for me,” he recalled.

One of the things he likes about the beach, other than just walking on it, is all of the wildlife that surrounds it. “There are birds, manatees and dolphins. There is always something going on.”

It makes sense that Dick would be attracted to Tampa and jumped at the opportunity to open RK’s Tampa office in the early 1990s. While he spent many years in south Tampa, he has found his way to Treasure Island and now lives just two blocks from the beach.

Dick claims to have zero musical talent, but his love of many kinds of music has led him to serve on the boards of the Florida Orchestra and the St. Pete Opera. “These organizations really do make an important contribution to the community,” he said.

As an example, he talked about the St. Pete Opera’s school outreach program. This year, the opera performed “Pinocchio” for third graders. It was adapted for children and tells a familiar story in a new and unexpected way and exposes them to the music.

Bud Kirk, Dick Caldwell and the late Thom Rumberger

“There’s this opera star in LA who was born and raised in St. Pete. Here she is a star 15 years later, so you never know the impact of something like this,” he said. 

Just like the impact of three lawyers who decided to create a different kind of firm. Each leaving his mark in a different way and creating a legacy they never dreamed, touching countless lives along the way.