Dick Caldwell Shares his Perspective on Building a Successful Practice and Changes that have Transformed the Practice of Law

01.19.18 | Permalink

In this second of a three-part series, Dick Caldwell talks about what it takes to build a solid reputation and win in court. He also considers the vast changes that have occurred over the almost five decades he has practiced law.


Bud Kirk, Dick Caldwell and Thom Rumberger

Many of the cases that Dick Caldwell worked on throughout his career were tough. The cases often involved catastrophic accidents where the injuries of survivors were severe and the jury was made up of people who knew the victims.

Dick talks about some of the key lessons he learned from one such trial early in his career that involved a huge crash at an intersection in Tallahassee where the cars caught fire.

“There were four deaths including one man’s wife, two kids and a young husband and father. The 23-year-old woman who survived was left unrecognizable from her injuries. This case was terrifying because the plaintiffs were so very sympathetic. We thought that if things went against us, we could set the national record at that time for tort verdicts,” he remembered. “This case involved a high speed crash that had catastrophic results for plaintiffs who were totally innocent, but we contended that it was not a product liability situation,” he noted.

“One of the keys to winning a tough trial like this is being prepared for every witness, every statement opposing experts make and outworking the other side,” said Dick. “We successfully tried that case in five weeks and upheld the verdict for GM all the way to the Florida Supreme Court. I learned so much technical knowledge from working with experts and dealing with a major case. By using the team concept, we kept everyone from having a nervous breakdown from overwork, but at the same time got the job done. It was such a valuable experience,” he said.

“As a lawyer, it is your responsibility to give your absolute best effort for your client,” said Dick. “It is your job to go the extra mile and work within the realm of ethics, good manners and common sense. People who are a success do that,” noted Dick. “That entails a lot of midnight oil, at least it did for me. But no matter what it takes, you owe that to the client,” he continued. “I’m convinced that we win cases because we outwork the other side. I might not be the most brilliant lawyer out there, but I’ll be darned if I’ll let someone outwork me.”

Giving the best effort doesn’t mean that the firm overworks its attorneys. “We are not a sweat shop,” said Dick. “We work hard and we have built a reputation that we require dedication to get the job done on behalf of our clients, but we also attract clients who take the long view-- what is needed now, in six months and a year from now?” explained Dick. “And we work as a team to get the results for our clients.”

Dick recalled another significant case where he learned the value of building a good case and presenting facts in a respectful manner to win over a jury—even one that personally knows the plaintiff. “This case was in Aroostook County at the very northern tip of Maine, right across the border from Quebec, Ontario. It was a very small community and we had a jury, most of whom knew the plaintiff,” recalled Dick. “It was catastrophic accident where the plaintiff was left a quadriplegic. The plaintiff was innocent—really was just in the wrong place at the wrong time. We laid out the facts, treated everyone with respect and hammered on the facts and the law. Seeing a jury return a defense verdict against someone they knew, really strengthened my conviction that juries, for the most part, try to be impartial and weigh the facts of the case,” he said.

Great attorneys enjoy the nuances of their cases and are fascinated by learning. “Every case is different, and I enjoy digging into the facts of the case, the different personalities and issues at hand,” said Dick. “I also like to figure out the arguments, position, discovery, depositions—it’s never dull. I tell new attorneys that boredom is not an occupational hazard of this job,” he laughed.

Dick admits that juggling personal and professional responsibilities was the hardest part of his job. “It takes an enormous effort to prepare these cases. You have to learn what you’re doing and apply that knowledge. You have to get the case prepared, retain experts, and take depositions of the other side’s experts and so on. A lot of the people you are talking to are scattered all over the country. As you get ready for trial, it just takes over your life. This is tough on family relationships,” explains Dick. “There were long periods of time that I would be gone—a month, six weeks on the other side of the country. It was tough and looking back I wish I’d handled some things differently.”

There is a lot more focus on balance these days and Dick believes that today’s attorneys do a better job of balancing personal and professional lives. “There is so much more focus on maintaining balance and people are smarter about how to handle it,” said Dick. “There have been so many advances in technology and other factors that have changed the way in which we work that also helps.”

For instance, Dick points to the use of technology and computers to streamline research and free up resources. If we were in trial and needed research, we’d have to borrow a law library or call back to the office to research a point of law and fax cases back and forth. We’re much more efficient now. When I was starting out, I could spent 8-10 hours on research whereas today you can spend an hour researching case law and still make it home at a reasonable hour,” said Dick.

“In addition to helping lawyers themselves be more efficient, technology has also had a big impact on law firms and freeing up resources that can be put to better use,” explained Dick. “For instance, 20 years ago, you had one secretary for every lawyer, but now lawyers are able to do so much more on their own, and more quickly, so that assistants are freed up to do other things and assist more than one attorney at a time,” said Dick.

Dick noted that technology is such an eminent part of practicing law that the Florida Supreme Court decreed that lawyers have at least a couple of hours of technology for Continued Legal Education.

In addition to the advancements in technology, Dick has witnessed a number of other changes in the landscape of trial law over his career. One of the biggest changes is how much harder it is to take a case to trial.

The risk of taking cases to trial has increased dramatically over the years, and this has of course been recognized by clients. “For example, there was this warranty case in Alabama against BMW. The customer was unhappy with the paint job. A young attorney handled the case and the jury came back with a $2 million verdict. It made it to the U.S. Supreme Court and was ultimately reversed, but that was a long effort and a lot of money over a $2,000 paint job,” explained Dick. “That type of situation has made business very reluctant to take a case to trial. Runaway verdicts have become more common. Every week there is another $150 million verdict and very few businesses can handle those results,” he said. “A lot of cases I’ve tried over the years would probably not see the light of day at present—and we won a lot of those cases,” noted Dick.


Dick says that today’s lawyers aren’t able to get the experience he was able to by trying so many cases. “You learn from the experience—having a witness say something you don’t expect or picking a jury,” said Dick. “It’s so much tougher to get hands-on trial experience.”

Another big change in the landscape of law is that there are more lawyers than ever before.
Dick noted that when he first started working in Orlando in late 1971, the entire bar association was around 400 lawyers—and very few of those were trial lawyers.

“Chances were great that you knew the lawyers on the other side. You knew what kind of lawyers they were. There was a collegiality among attorneys. If you needed a couple of extra days on something, you could call and it wouldn’t be a big deal. Today, there are so many more lawyers that we often don’t know the other side and we’ve lost the collegiality that there was before,” said Dick. “It’s much more defensive and more formal than when I first started practicing.”

Dick notes that clients have become more sophisticated today.
“One part of that is that as my practice evolved and grew, I started dealing more with general counsel of major organizations. That in itself has been quite a change, but overall, whether large or small, I feel that clients are more ready to handle the complexities of the legal system today. In order to serve them, you need to be just as savvy as they are,” he noted.

When talking with new lawyers, Dick says that communication is really the key to success. “I tell them that there is going to be a lot of stuff you won’t know a thing about and not to let that discourage them. That happens to everyone. Just don’t be afraid to ask questions,” he continued.

“I also like to point out that they have to put in the time to understand the cases, understand the adversary and know what we need to do to get this to a successful completion. That can take some time, particularly for young attorneys. Don’t be afraid to approach partners and ask what to do. Don’t be afraid to approach the client, either,” he advises.

“It’s also important to learn from disappointments and not get discouraged. You will lose cases and hearings, and there will be depositions that don’t turn out the way you want. Learn from these things and you will be successful.”

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