The son of Depression-era Tennessee carnies, Wilson Hubbard was smart, ambitious and always looking for a new angle. Nearly 100 years after his arrival in Pinellas County, and a quarter century after his death, the roots he put down in the Pass-a-Grille sand continue to flourish.
The Hubbard family has been synonymous with Gulf Coast fishing since the 1940s, when Wilson – just back from flying bombers in World War II – opened a small charter business at the 8th Street dock.
He’d purchased the dock as a teenager in the early 1930s; he rented rowboats and bamboo fishing poles, while he studied journalism and advertising at St. Petersburg Junior College. After the war, and after he married his high school sweetheart Lorraine Walls, he kicked things into high gear, changing the name to Hubbard’s Pier and christening himself Captain “Hub” Hubbard.
Today, the business is called Hubbard’s Marina, and it’s based at John’s Pass. There are 16 boats in the Hubbard fleet, including fishing vessels, sightseeing boats, ferrys and water taxis – and Dylan Hubbard, Wilson’s grandson, is vice president, manager and co-owner (with his father Mark Hubbard, the youngest of Wilson’s eight children).
“I would come down here when I was 4 or 5 years old,” 27-year-old Dylan remembers. “I’d sit in front of the office and catch pinfish – bait – for my grandfather. He would always sit out front, drinking his coffee and talking to customers.”
From the time he could walk, Dylan was either on the dock or on the boats, helping out and learning the ropes. Today, he is both an expert fisherman and a licensed captain.
It was never, he says, a foregone conclusion that he would be a professional Hubbard. “I was always going to be on the water and fishing, for sure, but as far as what I’m doing now, definitely not. I didn’t ever picture myself being in an office as much as I am – but unfortunately, there’s a lot of not-so-glorious parts about running a business.”
Mark Hubbard praises his son’s abilities, and his work ethic. “It’s not like a regular job – it’s more like a lifestyle,” he says. “I always explained to him ‘Don’t get involved to impress me, or to try to show me that you can do it. Do it for you.’ I’ve seen other family members have the wrong motivation going into this operation. It’s a lot of work, and it takes a lot of ambition.”
Wilson Hubbard’s list of firsts is impressive. His charter excursions and sight-seeing boats were the first in the area; in the ‘60s, he introduced overnight fishing trips to the further reaches.
Hubbard is also credited with introducing captive bottlenose dolphins to the bay area. It was 1954 when he trapped three animals and penned them, inside a half-submerged chain link fence, off Shell Key. His “party boat,” the Lucky Strike, would make stops at the island, and passengers thrilled as Captain Hubbard fed his “porpoises.” They did not jump or otherwise “entertain.”
The experiment didn’t last very long. When two of the animals escaped, Hubbard tired of the operation and sold the remaining dolphin to the John’s Pass Aquarium, where it lived in a dark, eight-foot-deep tank for the next 12 years. Its new owner taught the dolphin to jump through hoops and ring bells.
With that somewhat ignominious exercise behind him, Hubbard expanded his fishing charter business and began to establish himself as a local character. He wrote fishing reports for the St. Petersburg Times, and for years appeared regularly as an outdoors correspondent on WTVT-Channel 13.
“His whole life,” David observes, “was promotion, promotion, promotion.”
He and Lorraine were staunch Catholics, and they attended church, every Sunday, with all eight of their children.
In 1976, Hubbard left Pass-a-Grille for the more centrally-located John’s Pass, in Madeira Beach. He was instrumental in developing John’s Pass Village, buying up barely-developed acreage and relocating his fishing fleet to the John’s Pass docks. The Friendly Fisherman restaurant – named for one of his boats – opened in the late ’70s. Son Michael helped develop the annual John’s Pass Seafood Festival.
All seven siblings – James, 23, died in 1977 – were at one point involved in aspects of Hubbard business (“sweat equity,” Mark calls it) with mixed results. “There are a lot of stories like that,” says Dylan. “It’s part of working with family; you’ve got to grit your teeth.”
Not long after Wilson died in 1994, the family began to overextend itself. Hubbard Properties acquired a substantial amount of debt with a construction loan, intended for a massive expansion of its holdings at John’s Pass Village.
Lorraine, the CEO, announced her intention to liquidate the fishing business – Hubbard’s Marina – to finance the new development. Mark, who had by then introduced half-day trips and dolphin-watch tours, bought it from the family.
In 2007, Hubbard Properties broke ground on a five-story parking garage, 40,000 feet of retail space and a three-story boardwalk (the City of Madeira Beach owns the original John’s Pass boardwalk).
A perfect storm of red tide, a winter freeze, the BP oil spill and the country’s economic downturn changed everything. In 2011, Dylan explains, “We were a month away from signing Hooter’s. We would have been back in the black. But the lender came in and pretty much did a hostile takeover and forced our hand into bankruptcy. Because of that, we lost the property.”
The Netherlands-based Aegon Insurance, which had issued the $22 million loan, took over the property. “When we first went into bankruptcy,” Patricia Hubbard (Mark’s sister) told the Tampa Bay Times, “it was like going to the emergency room. We were put on life support. It became obvious we weren’t going to win this, so at some point you have to call in hospice.”
Hubbard Enterprises – the family business – still owns (but does not operate) the Friendly Fisherman restaurant (they pay rent on the building). Since Lorraine’s 2016 death, no one in the immediate family, with the exception of Mark and Dylan, has remained plugged in to the family business.
Dylan’s sister Corey has opened the family’s enormous, historic (1928) Florida home on Casablanca Avenue (near the Don Ce Sar) as a bed and breakfast.
They continue to try new things. Started in 2016, their water taxi service – connecting John’s Pass with Jungle Prada in St. Petersburg, and a Treasure Island restaurant landing – will cease operations this month. The Madeira Beach commission declined to fund the service for another year.
Mark Hubbard also owns the boat-building company Big Wave.
At this writing, the Hubbards’ former John’s Pass Village property is still on the market, for $18 million. “We originally offered to buy it back for $22 million,” Dylan recalls. “They said no. They lowered it to $21 million and no one wanted it. It sat on the market for eight years, and now it’s $18 million. It’s not worth what they’re asking.”
That sort of thing – big business and high finance – doesn’t appeal much to Dylan Hubbard, anyway. He’d rather be out on the water, catching fish.
His dad, he stresses, never pressured him. He went off to study business management at the University of Central Florida, with no particular intention of returning to the docks.
But Dylan Hubbard came home, of his own accord. “My father learned from his family’s mistakes, and that was one thing my grandfather did to his son – ‘whenever you want it, this is yours’ – so my dad’s brothers grew up trying to work in the business trying to please their father. To get him to say that he was proud of them.”
He’s looking at the future as well as the past. “Wilson Hubbard was a good salesman, a great speaker and a great writer,” Dylan opines. “And a very wise businessman. My father is as well, and I’d like to think that I will be one day.”
The Hubbards are deeply committed to environmental education and conservation. Their floating classroom, Environmental Explorer, enables students to observe native wildlife in its natural habitat, explore and understand wetland environments, and discuss current environmental issues with the ship’s on-board naturalist.
“To me,” Dylan explains, “it’s not so much a legacy as it is being involved in the community. And giving back. We have to take care of our fishery, and our community.
“That’s what keeps us going, because you can advertise all you want, you can spend money on TV commercials, but if you don’t treat your community well, and you don’t have that word of mouth, it’s nothing.”