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Vintage Pinellas: The enigma of Captain Wilson Hubbard

Bill DeYoung



"I never realized how lucky I was until I went all over the world as an Air Force pilot in World War II," Wilson Hubbard (shown here in the early 1960s) once reflected. "The more I saw of the rest of the world, the better the west coast of Florida looked to me." All images provided by the Hubbard family.

He operated the most lucrative fishing-excursion fleet on the Gulf Coast, and knew the waters of the Pinellas barrier islands, every fathom, by heart. And Wilson Hubbard, the only child of traveling carnies, also knew how to spin a yarn – a fish tale – when it was to his advantage.

“I’m a pretty good fisherman,” Hubbard once told a reporter, in a rare moment of candor, “but I’m a better businessman.”

For four decades, Hubbard’s name was virtually synonymous with Pass-a-Grille, where he turned a modest bait-and-tackle concern into a profitable charter and party boat business.

He then left that little beach town for more populated John’s Pass, and expanded his empire. Hubbard died in 1994, but the business – Hubbard’s Marina – lives on, operated by his son and grandson.

Wilson Miller Hubbard stood six-foot-two. He was thin and lanky, handsome, smart and clever, determined, fearless and tough-as-nails.

“He was a workaholic,” recalls Kathleen McDole, the third-born of Hubbard’s eight children. “He got up at 6 in the morning and didn’t come home until 6 at night.”

Still, she adds, “he took people fishing and he taught them how – but he really didn’t like to fish all that much. Even though he did, because he had to.”

His own father, George Edward “Ed” Hubbard, had come from Cairo, Illinois. A taciturn fellow who rarely smiled, he co-owned a small carnival that traveled up and down the Midwest, the corn belt and the south in the 1910s and ‘20s. Ed was the advance man – he’d go to the next town on the list and make the necessary arrangements – and a roustabout (setting and tearing down the tents), and a sideshow barker.

He was also a card shark, who’d set up a friendly game of poker out back and regularly separate the yokels from their hard-earned cash.

Eighteen-year-old Anna Grace Miller of Clarksburg, West Virginia was so taken with the show – and, apparently, with Ed Hubbard – she ran away from home and asked to join the team. She became Madam Anna, the palm reader, and married Hubbard in 1916, when she was 21. Wilson was born that same year, during a stopover in Memphis.

A Georgia cousin took him in, once he’d reached school age, so Ed and Anna could continue traveling. A deal was struck for Wilson to join up with the carnival over the summers. Eventually, he stayed on and began working for his keep – as a roustabout, a girlie-show barker, a lightweight boxer, whatever needed to be done.

“For a kid growing up, it’s the loneliest life in the world,” he would reflect many years later. “Every week you’re the new kid on the block, and every week you got to go out and fight somebody.”

And fight he did.

Michael Hubbard, Wilson’s eldest son, recalls a story his dad once told him.

“My grandfather would cheat ‘em out of their weekly paycheck. They’d go home, and there was hell to pay with their wives. And so their kids would come to the carnival the next day, looking for somebody to get even with.

“So here’s my dad, 12, 13 years old, he’s chipping ice from a 300-pound block. And he said a group of these country roughnecks surrounded him. They were going to gang him up. There was nobody else in sight. He tried to think of what to do to kind of subdue things.

“He had been practicing throwing his icepick, and sticking it in a tree. So he took the icepick and threw it at the biggest guy, the one who was runnin’ his mouth. He tried to throw it at the ground between his feet. But he hit the guy in the kneecap. The icepick stuck in the guy’s kneecap. You can imagine what that feels like. The guy’s frozen.”

Young Wilson, so the story went, seized the opportunity. “My dad yanked it out and said ‘All right, who’s next?’ And they all backed down.”

That at-all-cost instinct for survival, Michael believes, was passed down from Ed Hubbard. “Dad learned how to be a good boxer on the carnival. He would knock local boys down, let them get back up, and knock them down again.

“His dad screamed at him, ‘Don’t let them get up! Jump on them and finish it! And don’t use your fists! Use a hammer!’ He told him to hold the hammer with the head in his hand, so they can’t take it away from him, and hit them with the handle end.”

The arrival of the Great Depression meant the end of the road for the carnival, and on the last journey south the Hubbards found themselves in Pass-a-Grille, Florida, population 162. Wilson was 14.

Ed soon realized there were wealthy winter residents who enjoyed a good game of poker. So they stayed. Anna opened a Pass-a-Grille palm-reading shop inside a beach hotel, and their son enrolled at St. Petersburg High School.

On the Pier: St. Petersburg High School student and teenage entrepreneur Wilson M. Hubbard.

He also got a job, aiding the man who ran the rowboat-rental concession on the city-owned 8th Street Pier. Every late afternoon, after school, Wilson procured bait for the pier. He caught pinfish in Boca Ciega Bay; he rowed out to the abundant grass flats around Pine Key and caught shrimp – lots of shrimp – with a push net, strapped to his back. He snorkeled the bay for stone crabs and sold the claws door-to-door.

When the bait shop proprietor decided to give it all up after an injury, he sold the business to Wilson Hubbard for $40, and his small contingent of rowboats and cane poles for $150. Because he was too young to sign the city’s lease transfer, his father did it for him.

At St. Petersburg Junior College, Wilson was on the fencing team and studied journalism; he even wrote stories for the Gulf Beach Journal. Filled with boundless curiosity, and ever-ambitious, he saved enough money to take flying lessons, at Albert Whitted Airport, and earned his piloting license.

He was drafted in 1942; when the Army discovered their newest recruit was a licensed pilot, they sent him to twin-engine school and commissioned him a captain in the Air Corps. He flew reconnaissance missions over enemy territory, but a life-threatening knee injury meant re-assignment – no longer fit for “active service,” he spent the last two years of World War II delivering bombers to airfields in Africa and Allied Europe.

In his off hours, he played a lot of poker.

He’d been promoted to First Lieutenant, but he preferred to be called Captain Hubbard – the title was perfect for the occupation he had waiting for him back home in Florida. When he started wearing the white yachting cap that would become his trademark.

The county’s inshore waters were teeming with fish in those days, with trout and giant tarpon, and offshore, the Hubbard-borne anglers were reeling in grouper and reds and jacks and snapper.

Ed Hubbard died of a heart attack in March, 1946, which left Wilson and his mother the co-owners of what would soon be known as Hubbard’s Pier. But Anna was not crazy about the fish business, and Wilson, using the $15,000 he’d saved up by hustling other officers in late-night card games, purchased the Girard General Store and apartment building on 8th Street, close to the pier (“it took three money belts to get my winnings back into this country after the war,” he bragged). He gave it to his mother to operate; the business was re-christened Hubbard House Hotel and Captain’s Table Restaurant. Anna (her grandkids knew her as “Hubba”) was the proprietor until it finally shut down in the ‘70s.

Lorraine Walls, from Chicago, had just moved to the area when she met Lt. Wilson Hubbard, home from the war, at a school carnival. He was broiling mullet, she remembered, over old mattress springs, and she thought he was ever so handsome.

According to Kathleen McDole, the second time she ran into Hubbard, he was in his uniform. “He said ‘hello!’ and she dropped her ice cream.” And so the romance began.

Lorraine’s father, Harry James Walls, died when she was small. The hard-drinking Irishman, who worked as a lifeguard on Lake Michigan, had accidentally killed a man in a street fight and spent a year in prison.

Like Wilson Hubbard, Lorraine was an only child.

In less than a year she and Wilson were married, and son Michael arrived. The Hubbard family was one of three that homesteaded on primitive Pine Key – what’s now known as Tierra Verde. Hubbard paid $500 for two lots and bought a prefabricated house from the Adirondack Housing Company of New York.

The pieces were shipped down in a boxcar, trucked to Pass-a-Grille and ferried, in pieces, to Pine Key aboard one of his boats. He assembled it himself.

After Michael there was Patricia, then Kathleen, then Tommy. Four kids in four years.

McDole’s memories of those early times include a well pump in the kitchen sink, a generator with one electric lightbulb, kerosene lamps and a chemical toilet. “My mother had to paint the screens with kerosene at night, so the bugs didn’t get in,” she recalled. Lorraine washed diapers in a small clawfoot tub her husband picked up somewhere, using seawater and “a whole box” of Dreft laundry detergent.

Michael remembers this as one of the best times of his life.

The family lived on the island for six years. Wilson built a small boat for Lorraine to ferry the children to Pass-a-Grille. When Michael was old enough to start school, however, she balked and insisted they find a house on the “mainland.”

All the Hubbard children attended St. John Vianney Catholic School. “She knew where he came from and how he was raised,” McDole explains. “So she made a deal with him. She goes ‘You raise the boys, and I’ll raise the girls.’ So needless to say, I never had the conversation with my dad my whole life. My mother sent us to the Catholic school, so she figured we were all good.”

Hubbard converted to Catholicism, and the family rarely missed church on Sunday.

Hubbard’s Pier began adding half day charters and longer (even overnight) excursions. Hubbard added “party boats,” allowing for more passengers per trip. He earned a reputation as the best fishing guide in the county, and was hired to give live reports on Ernie Lee’s WTVT-Channel 13 morning show.

During sightseeing day trips to Shell Key, across the water at Pass-a-Grille’s south end, tourists would scour the sand for prizes. Hubbard, with all his carny DNA intact, wanted to be ensure they had a good time and would return to pay him another time. “I wasn’t above taking a bushel basket full of shells and strewing them all along the beach,” he later confessed to the St. Petersburg Times.

He served as President of the St. Petersburg Beach Chamber of Commerce, and unsuccessfully ran for city commission.

And the children kept coming – by 1964, the family included Jimmy, Jeffrey, Jacqueline and Mark.

Casablanca family portrait, 1966: From left Wilson, Lorraine, Van Cecil (Patricia’s husband), Michael, Patricia, Kathleen, Tommy, Jimmy, Jeffrey, Jacqueline and Mark.

They grew up in a big, circa 1928 house on Casablanca Avenue, in the shadow of the Don CeSar hotel. Once the boys turned 12, they were required to help out with the family business. They learned boats and they learned fishing, and they learned the art of people-pleasing (sometimes through clenched teeth). They also learned to fight.

“Wilson’s raising the boys,” McDole says, “and he’s teaching them to fight, but also, ‘whatever you do, don’t get caught.’ That was the mantra for those boys.”

The boys learned to crave his respect, and to fear his temper. There were spankings, and worse, especially when one of them had mouthed off to their mother. Wilson would get an earful when he got home and administer “punishment.”

He had regular poker games at the house; he and Lorraine hosted serious into-the-night cocktail parties.

Mostly, says McDole, her father worked. “He was a big reader. He would read constantly. He would come home from work, each dinner, and go to bed and read. ‘Where’s you dad?’ ‘He’s got a book in front of him.’ Mom would have to drag him out to events and stuff.”

He was partial to Zane Grey westerns, and science fiction novels.

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 docks. The Friendly Fisherman restaurant – named for one of his boats – opened in ’79.

There have been some pretty stormy seas. Jimmy Hubbard died in 1977, at age 23, from a drug overdose. Two other Hubbard sons did jail time for drug offences – one for selling, the other for smuggling.

“I’ve never smuggled drugs because of my wife,” Hubbard said in a 1979 interview. “She went to pieces when my boys got busted for marijuana. I wouldn’t want to put her through coming to see me in jail.”

However, he added (with a wink) that if he really, really needed the money to support his family, he’d do it. “If a doctor told me I had a short time to live, I’d be looking for someone to make a connection.”

Hubbard was 78 years old when he was felled by a heart attack on Dec. 1, 1994. To the very end, Michael remembers, “he’d put the boats out in the morning and sit out on the pier, and hold court. And tell war stories.” Lorraine died in 2016.

Mark, the youngest son, owns Hubbard’s Marina and the modest fleet of charter, party and sightseeing boats it operates out of John’s Pass Village, along with his hands-on son Dylan, who is “Captain Hubbard” for the 21st century.

Members of the family still own the Friendly Fisherman restaurant, on the boardwalk next to the marina.

Wilson Hubbard was asked, in one of his last interviews, what retirement might look like for him.

“I never expect to sit around the house,” he replied, “and I never expect to quit making money. It’s too much fun.”










































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    Al Braithwaite

    July 17, 2023at11:56 am

    Nice story, Bill….as a 46 year resident of Pinellas County, I knew of the Hubbards, both when they operated their businesses in Pass-a-Grille, and as former Finance Director for the City of Madeira Beach, later as we did business with them as property owners and merchants in John’s Pass Village. I knew the Captain in his later years, and it was a nice article to talk to family members and learn a little more detail about the family and their history, both business and personal.

    Well done. Would enjoy seeing more articles like this.

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