Dennis Bailey – Merlin Law Group

When Dennis Bailey was beginning his career as an attorney almost 40 years ago, his father, Pat Bailey, advised him to become a legal generalist.

His father’s law firm in Pompano Beach, Florida, handled cases ranging from helping set up businesses to divorces, wills and litigation. When Pat Bailey went to the grocery store, he was routinely greeted by the people he’d helped, a constant reminder of the impact of his work.

Dennis Bailey | General Counsel | Merlin Law Group

In his career, Dennis Bailey has served as a prosecutor and criminal defense attorney, litigated civil cases for plaintiffs and defendants—with more than 200 cases tried by juries. He also spent six years as a circuit judge for Florida’s Seventeenth Judicial Circuit, located in Fort Lauderdale, and he and his brother, Tim Bailey, became the first brothers to serve simultaneously on that bench.

But it’s only now that Bailey feels like he’s fulfilling the role of a generalist as general counsel and trial attorney at Tampa-based Merlin Law Group. The firm represents plaintiffs in cases against insurance companies.

As head of the firm’s trial division, he (and managing attorney Michael Duffy) continues to represent clients when cases reach courtrooms. Bailey also manages the firm’s legal affairs and provides advice and counsel to attorneys on everything from mediation strategies to presenting a case to a jury.

“I feel like I’m walking in my father’s shoes now,” Bailey says. “But his client was the neighborhood and my client is the law firm.”

David v. Goliath

Merlin Law Group was founded in 1985 as Bailey’s legal career was beginning and considers itself “the policyholder’s advocate.” The firm has 11 offices and its 43 attorneys are licensed to practice in 29 states. He joined the firm in 2021 after his six-year term on the bench in Broward County.

“We’re a boutique law firm working on a national scale,” Bailey says of cases filed in state or federal courts. “Hiring Merlin is like bringing in a ringer because it changes the whole dynamic.”

The firm handles mostly property and casualty insurance cases—including damages from natural disasters or caused by fire and smoke, water, wind or hail.

“It’s an area that’s the best example of David versus Goliath,” Bailey says. “The insurance industry is powerful and it has means to procure great representation while people who are being insured don’t have those means. We balance the playing field.”

However, he adds this is not the kind of dramatic legal work seen on TV or movies because insurance policies are so complex that juries don’t find them exciting. In fact, more than 97 percent of cases taken by Merlin Law Group are settled before they reach a trial.

Bailey says the increase in court-ordered mediation or arbitration to settle disputes is one of the biggest changes he has seen in his career. Though the services can reduce case logs and court expenses, he says attorneys who once tried 10 or 12 cases in court annually now can go years without approaching a jury. That’s a challenge to an attorney’s professional growth.

“You can’t tell someone how to try a good case. They have to be on their feet in front of juries,” Bailey says.

Show your cards

Creating strategies for mediation and arbitration as well as taking deposition from experts to build cases are crucial topics Bailey has brought to the fore in the monthly virtual seminars he organizes and leads for Merlin Law Group.

While he didn’t originate them, Bailey was asked by founder William “Chip” Merlin to rejuvenate the seminars shortly after he joined the firm in 2021. The seminars last from 60 to 90 minutes and Bailey says he’s never at a loss for topics or speakers, including industry experts such as a meteorologist or experts on legal ethics.

The seminars also tap into Bailey’s teaching experience—he’s taught law at Nova Southeastern University (where he earned his J.D.) and the University of Miami as well as law and evidence at Broward College Police Academy; he’s also instructed judges at Florida Judicial College. The seminars count toward the annual continued education requirements for attorneys.

Where Bailey says he always approached a case by understanding what a jury was looking for and speaking to it, he says developing attorneys need a different approach.

“You don’t always need to be a dynamo in the courtroom,” Bailey says. “Don’t hide your cards in mediation, either. So many cases are settled before trial, and if you have right on your side, showing your cards is the best thing you can do.”

On the right side

Bailey says his work at Merlin Law Group is akin to his work prosecuting, especially child sexual abuse cases, in Broward County because “my job is to go to court every day and do the right thing.”

Though he’s one of three brothers who followed their father and grandfather into law, Bailey says he aspired to become an architect and studied at Notre Dame University but disliked the required math. So, he transferred to Florida Atlantic University and earned a bachelor’s degree in English, then graduated from Nova Southeastern University Shepard Broad College of Law in 1985.

Bailey then spent 10 years prosecuting cases as an assistant state attorney in Broward County before defending clients throughout the Sunshine State in private practice. Six of the defendants he represented faced the death penalty and none were sentenced to it.

His work in civil practice included representing Fortune 500 companies and homeless plaintiffs in federal Civil Rights litigation. Outside his practice, Bailey researches and has written several unpublished novels about Biblical history.

“The length of time I have been doing this and walking the earth makes me a better lawyer,” Bailey says. “At this point in my career, I truly enjoy being able to able to pass my knowledge on to younger attorneys.”

View this feature in the Vanguard Summer III 2023 Edition here.