Hugh Cotton Insurance Thrives For Three Generations

Providing Central Floridians with peace of mind for three generations, Hugh Cotton Insurance covers it all with aplomb—and current president and CEO Tom Cotton has the stories to prove it.

Hugh Cotton posing with his 1968 Camaro. (BILL FREDETTE-HUFFMAN)

In 1948, the post-WWII boom was in full swing when Hugh Cotton, Sr., opened an Orlando bar he dubbed The Royal. The retired insurance company executive had dreamed of tending a watering hole where locals could dance, play shuffleboard and gossip over a Tom Collins or whiskey sour. By day, insurance was his game in the form of a little downtown agency, Hugh Cotton Insurance. When Hugh, Sr., died unexpectedly, his son, Hugh, Jr., sold the bar, shut down his timber company and stepped in to build the insurance business.

Fast-forward several decades. The house of Mickey had come to town and local tourism was growing faster than you could redeem your E-tickets. Beefy King already had been serving its now iconic roast beef sandwiches for a decade. Hugh’s grandson, Tom Cotton, a freshly-minted 1978 Boone High School graduate, wasn’t dreaming of following in his dad’s footsteps. An adventurous teen who pedaled his bike to Wekiva State Park to camp with friends and who boated and waterskied on local lakes, Tom thought he’d join the Marines. But his dad made him an offer he couldn’t refuse: “Just try the top-rated insurance program at Florida State University, ‘and if you don’t like insurance, I’ll send you to any school in the world to study anything you want, or you can graduate and go into the service as an officer.’”
“I thought he didn’t love me because he was a die-hard Gator fan,” Cotton recalls, laughing. “But that’s when my world changed. I loved it up there. It’s where I met my wife. And he was right, I got to study under the brightest minds.”


Until he was 4 years old, Tom and his family had lived in an apartment above the familiar Curry Ford Road offices his father built in 1950. Except for his move to Tallahassee, Cotton has never lived more than a mile from the office. In 1999, he took over as president and CEO. Today, Hugh Cotton Insurance is the oldest (74 years), largest privately-held agency in Central Florida, insuring individuals, mom-and-pop businesses and multi-national corporations that employ thousands. Hugh Cotton’s local “world headquarters” employs 14.

Claims for the Books

After years of success as a third-generation insurance man, Tom Cotton has seen nearly every claim imaginable, from hurricane-damaged roofs to ransomware attacks.

And then there was the case of the dog bite. A man was wandering around a warehouse insured by the Cotton firm. “He walked around the corner and the dog clamped down the nearest place a dog can bite.” Ouch. It was the largest claim his agency ever paid.

One claim settled by Cotton’s agency was that of a client who became a good friend. Mark Whitmire’s 75-year-old Whitmire’s Furniture building, another historic local business, lost its roof during a microburst, a small but damaging downdraft from the core of a storm.
“It came out of nowhere and lifted the roof straight off our store,” says Whitmire, now a hunting pal of Cotton’s who admires his friend’s insurance business savvy. “Tom was on that immediately. His knowledge of the industry is second to none.”

Hugh and Tom Cotton of Hugh Cotton Insurance. (COURTESY HUGH COTTON INSURANCE)

Insurance—It’s No Joke

Insurance jokes are a dime a dozen. Fleetwood Mac got insurance for “Landslides.” Adam and Eve needed coverage. What’s the perfect name for a life insurance salesman? Justin Case.

But it’s no joke if folks don’t have adequate coverage and wind up suffering a disaster, an accident or another life-changing event. And Cotton has learned through experience that being prepared means more than just covering every policy base.

In 2004, when Hurricane Charley blew into Orlando, the Cotton firm’s largest homeowner insurance carrier was Penn Charter, located in the small town of Lititz, Pa.

“Charley hit on a Friday. Saturday, our world changed,” he recalls. “We had 2,000 policies with Lititz, and Lititz is not answering the phone. We got hold of the president—tracked him down on his cell phone—and he goes ‘We’re having a parade!’ I said we’ve got a catastrophe here, so by 2 o’clock on Saturday, Lititz had their offices up and running.

The original Curry Ford Road location. (COURTESY HUGH COTTON INSURANCE)

“The insurance industry is doing a better job now. And I’ve got a 70-kilowatt generator sitting in my parking lot ready to go,” he says. “I have to be ready to go. I can tell a business how to prep, and I can tell you how to prep your house for a storm.”

He also can tell you that, as our high-tech world changes, cyber insurance coverage to protect against hackers and ransomware is something many businesses haven’t considered. “If you click on the wrong link coming into your email or text, bad things happen,” Cotton warns. “Cyber insurance helps you restore your data, negotiate and pay the ransom.” It also pays for the business’s down time, credit monitoring of customers whose personal data has been hacked and more.

“Average ransom has gone from $5,000 to $320,000. It’s a feature product for us. It’s very technical but it starts the conversation: What do you do to protect yourself?” he says.

On weekends, when Cotton’s not preparing for worst case scenarios, the married father of three takes out his boat or races his prize 1968 Camaro on the east end of town.

He and his buddies also hunt wild boar and alligators. Is there a liability policy for that? You bet. Cotton formed his own insured adventure-guide company—Eagle Outdoors—to be sure he’s covered.

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