Arts + Culture

Pirates and Pyramids: The Folklore of Southwest Florida

Dive into the legends of Southwest Florida—colorful tales that might even have some truth to them.

BY December 12, 2018

What makes a region distinct?

Well, the accents, of course, or the colloquialisms (right, y’all?); the funky traditions (Mango Queen? Mullet toss?); the attire (year-round flip-flops); and, our favorite, the stories. Every place has them—folktales and legends that blur truth, half-truth, hint-of-truth, and the totally-no-way-that’s-true.

We’ve dug up some local lore for you—lest you think our great subtropical suburbia sprung from the swamp along with Disney World circa 1971. There’s your first myth—debunked.

Our disclaimer: We’re no historians. We’ve culled various books and websites and, in a few cases, called on those in-the-know to pull together these Southwest Florida tales, some very old, some more recent. So fry up some gator tail, pour a sweet tea, and enjoy stories from the state weird enough to sustain Twitter by itself should it ever be called upon to do so.


The biggest clues to a region’s past are in its names: Collier County, Hendry Street, Manuels Branch, Wiggins Pass—stalwart pioneers of Fort Myers and Naples. But behind other names lies a darker legacy.

Like Captiva. The infamous Jose Gaspar reportedly held women captive on this barrier island until their ransoms were paid. Gaspar, who was swashbuckling in the late 1700s and early 1800s, is our best-known pirate, and the force behind many of Southwest Florida’s more scurrilous episodes. Short of stature and outsize in temper, Gaspar is better known as “Gasparilla,” as in Gasparilla Island off the Lee County coast where the pirate headquartered his operation. Legend has it that he kidnapped a beautiful Spanish princess, Useppa (or Joseffa by many accounts), took her to an island even more isolated than Captiva and made repeated advances at her. The woman held firm in her refusal until the incensed pirate sliced off her head.

Naturally, her namesake island is said to be haunted by a headless ghost.

At age 65, Gasparilla decided to pull off one last heist, retire and distribute his wealth among his crew. He identified a British ship to make his final victim. But the ship wasn’t British at all—it was the USS Enterprise, a Navy warship, determined to snare the old pirate. Facing the imminent destruction of his Floridablanca, the pirate captain wrapped anchor chains around his waist and jumped into Boca Grande Pass, reportedly shouting, “Gasparilla dies by his own hand, not the enemy’s!”

His treasure was never fully recovered, though in 2015 a brother and sister who were cleaning out their grandfather’s attic in Tampa found a box containing a skeletal hand, a tattered map of the Hillsborough River, old coins and a photo of a couple who may have been their great-grandparents. As children, their grandfather had told them stories about how his father had recovered part of Gasparilla’s treasure. While we can’t attest to the veracity of the old legends, the family discovery is absolutely true. We read it in the news!

[Incidentally, Gasparilla Island was later found to contain loot of a very different sort—phosphate. By the early 1900s, Boca Grande, the island’s hub, had become the nation’s fourth-busiest port and supplied half the nation’s phosphate. Also famous to Gaspar’s former stomping ground is the 106-year-old Gasparilla Inn & Club, which boasts drawing celebrities including Thomas Edison, Harvey Firestone, Katharine Hepburn and the George H.W. Bush family.]

Lovers Key

The official story is that this once-secluded key got its name because of the young lovers who used to go to there for some “alone time.” We like the version Elizabeth D’Onofrio of Fort Myers Beach tells better. D’Onofrio, actress, director and big sister of Law & Order’s Vincent D’Onofrio, has a fascination with pirate lore. A few years ago, she directed an adaptation of Sisters of the Sea, a novel by Sandra Riley based on the true story of two women pirates, Anne Bonny and Mary Read, who served together in “Calico” Jack Ratham’s crew.

D’Onofrio tells the story behind the key’s naming this way:

In the 1700s, Jack and company were sailing near the Florida Keys. In hot pursuit was a Spanish galleon, no doubt after Jack for one misdeed or another. A storm overtook the two ships, sinking the Spaniards and sweeping the pirates up the Gulf Coast, all the way to present-day Lee County. Lovers Key, insists Elizabeth, was named for Calico Jack and his sweetheart, Anne Bonny.

Like Elizabeth (who plays a female marauder on a local pirate cruise), we found the lure of the “girl pirates” irresistible and wanted to know more. Anne, according to our research, was fierce—killing a servant girl in her youth, nearly beating to death a man who tried to rape her and silencing a disparaging shipmate by stabbing him, according to legend. Her “bestie,” Mary, was a cross-dressing sailor whom Calico Jack had captured while raiding the Dutch ship on which she served. No one realized Mary’s gender—she was a ruthless fighter with a mouth that might make even a pirate blush. The story goes that an unsuspecting Anne (hardly known for fidelity) made a pass at her. Mary, wanting to stay in Jack’s good graces, let Anne in on her secret to thwart any improprieties. The two became friends. But their girl-talk time did eventually rouse Jack’s suspicions, and Mary revealed herself to him, too—literally, opening up her baggy tunic to give a jealous Jack proof of her womanhood.

Says Elizabeth: “I think I liked them because they just wanted adventure. They went against the norms—they had ambitions that only men had at the time.”

That may be so, but what a perverted twist on “girl power” were they!

[Near Lovers Key is Black Key. It’s reportedly named, says Debbie Voorhees of the Friends of Lovers Key, for Augustus Black, who’d escaped capture when Gasparilla’s ship was sunk. Black is believed to have lived out his life on that island. He was rarely seen, trading goods with a family squatting on Mound Key, and quite possibly receiving care by another family as he neared death. There are a couple of accounts of Black giving one or the other of these families a black lump that is believed to have been gold melted down and tarnished, but it appears the recipient was later swindled out of the riches. What a fitting end to a pirate tale!]

The Pyramids

One afternoon in the Gulfshore Life office, we stumbled across a reference to the Pyramids in San Carlos Park. None of us—not yours truly, a 19-year Fort Myers resident, not our Naples-born managing editor—had ever heard of such a thing. A Google search ensued, and, sure enough, we hit on the homepage for “Pyramids in Florida.”

Still disbelieving (’cause you can’t trust everything on the internet), a road trip to San Carlos Park was in order. And so on a Friday afternoon, this intrepid reporter turned into the neighborhood, a modest collection of ranch homes and duplexes. Just a few hundred feet in, there it was: a sign directing visitors down an access road to the resort.

At the entrance, guests are greeted by “private property” warnings, security cameras and (insert dramatic pause)…

… a giant, white bust of Beethoven upon which is carved a sign, “New University Pyramid Village.” And, yes, there are pyramids: 40-foot-high glass structures gleaming in the sunlight.

The office was locked tight, not a soul was in sight, and the whole place looked like some otherworldly beings had abandoned their Earthly colony. It was downright creepy.

A phone call to the resort office that next Monday got us a recording (in English and German) but no real person (and no return call).

More Google searching, then. Apparently, the land was purchased years ago by an Austrian couple—a holistic doctor and an engineer—who believed the 9-acre property was a power hot spot based on the geophysical forces emitted from the ground. Perhaps its no coincidence that the Koreshans, a 19th century utopian religious community—or cult, depending on your viewpoint—set up shop just up the road.

And then, a few weeks after our visit, the pyramids hit the front page of the local daily newspaper (what timing!), part of a story about unique Airbnb rentals in Southwest Florida. Ah-ha! We should have known this New Age-y property would not stay mired in the old, traditional ways of reserving lodging.

The one thing we still haven’t figured out: why the founders erected their ode to Beethoven, except for the composer’s ties to Austria, where he was a favorite among the Viennese aristocrats of the 1700s.

The Skunk Ape

We simply couldn’t leave out the skunk ape in any compilation of Southwest Florida folklore. We even made quick trip to the Skunk Ape Headquarters in Ochopee. After all, how many kitschy roadside attractions do we have left?

And kitschy it is—with the sculpture of a smiling, gorilla-like humanoid greeting visitors in the parking lot.

These days, the headquarters is more gift shop and campground office than skunk ape shrine, but in one corner is posted the photo that started it all—the one David Shealy shot in July 1997 on a disposable camera that shows the “evidence” as clear as day: a hairy, ape-like figure in broad daylight trudging through the grasslands, its back to the camera.

Shealy, who has been featured on everything from The Daily Show to CBS News to the Miami Herald, was out of town the day we stopped by, but we found plenty of his “data” on the website The apes, apparently, stand up to 7 feet tall; sport a coat of reddish-brown fur; eat an omnivorous diet; generally, but not always, travel alone; and smell absolutely terrible, like rotting eggs or methane gas.

Shealy isn’t the only one spouting skunk ape tales. Thomas Lockyear, who runs the Museum of the Everglades, has heard stories of the creature woven into the history of the Florida Keys and the state’s native tribes. “This is Florida’s last frontier,” he says of the Everglades. “If it is going to hide anywhere, this would be the place.” He calls cryptozoology a “fascinating field,” and with a grin, he admits: There’s a skunk ape sticker on the back of his car.

Birthplace of the Bay of Pigs

We already told you about the tragic tale of Joseffa, namesake of Useppa Island. But the island holds another unusual claim to fame.

In 1960, the CIA approached the Colliers, who owned Useppa, about using the then-uninhabited island for a clandestine training mission. The family agreed, and the spy agency quietly began recruiting Cuban exiles from Miami to join a secret mission to overthrow Fidel Castro. This retelling is by Gar Beckstead, the current owner of Useppa, in a documentary produced for C-Span.

Nearly 70 Cuban men camped out on Useppa, undergoing CIA psychological vetting and training to operate radios and perform clandestine activities (war games would take place later, in Guatemala). The U.S. government’s initial plan had been to send in guerrilla operatives to incite a grassroots movement to unseat Castro. That, of course, morphed into a full-blown 1,400-person invasion—an infamous American flop. Most of the invading exiles were either killed or captured by the Castro regime.

Bay of Pigs survivors return periodically to Useppa. Those first recruits, Brigade 2506, have held 25th- and 50th-anniversary celebrations there.

“These are truly a band of brothers who went through great, great hardships and have very, very strong feelings about patriotism, about Cuba, about Castro and so forth and carry the stigma of the failed Bay of Pigs … and that hurts these gentlemen very much,” Beckstead told C-Span.

Ponce de Leon

The Spanish explorer Juan Ponce de León gave Florida its name, fed our obsession with youth, did the standard European explorer thing of claiming land and ravaging it for gold. And then he came to Southwest Florida, where the natives would have none of it.

In February 1521, de León left Puerto Rico for his second expedition of Florida. He and his crew landed near what is now Charlotte Harbor, with the intention of starting a colony. And that’s where they met the Calusa, the tribe that controlled Southwest Florida. Their name, incidentally, means “fierce.” It might have been nice for de León’s sake if someone had tipped him off to that.

Historical records are as spotty as you’d expect, but it’s widely believed that the Calusa struck the explorer with an arrow—quite possibly poisoned. His crew whisked him to Cuba, but the wound was a mortal one, and a few months later, de León died.

Thanks to the Randell Research Center, an archaeological site on Pine Island, we were actually able to do a little fact-checking on this one. Cindy Bear, the programs and services coordinator, has a ready response to the question on the explorer-native skirmish—clearly having answered it many, many times.

It’s become fixed in people’s minds the exact location of where the Calusa-Spaniard skirmish took place and in the exact location where de León received his wounds—the buttocks, the thigh, the ankle, Bear says. “All or any of that’s possible, but not validated,” she says.

We know she’s right. But the poison arrow thing makes a darn good tale.

Killing Mr. Watson

There’s a sign at Ted Smallwood’s historic trading post in Chokoloskee that reads: “Killing Mr. Watson was a community project.”

Does that get the storytelling juices flowing or what?

This story of vigilante justice comes to us courtesy of Glenn Miller, a local reporter and the president of the Southwest Florida Historical Society. According to him, Mr. Edgar J. Watson was a despicable character, who allegedly killed his employees on payday rather than fork over their due.

A band of 12, 15—maybe 20—men met Watson’s boat on Oct. 24, 1910. “This wasn’t a welcoming party,” Miller observed wryly in his published re-telling of the story. Watson may have tried to fire his rifle, but he was no match for the firepower on the shoreline.

Now, that wasn’t at this store, explains Wesley Markley, who married into the Smallwood clan and was working the counter one day at the old trading post, now a museum, which we simply had to visit. The murder took place at Ted’s original shop, run out of his house about a 100 yards through the mangroves, Markley says.

The Watson display sits at the store’s center and is full of old photos, old sketches and handwritten notes explaining the art. By one photo, “Mamie Smallwood sold Mr. Watson damp paper shotgun shells.” By another, “They were convinced that he was shooting his farm workers on pay day and feeding them to the alligators.” Above, on a high shelf, perched a yellowing book with a picture of a rifle-toting woman and another handwritten sign: “Watson’s most famous victim was Belle Starr. Belle, the famous Bandit Queen, rode with Jesse James.” The two, Markley says, encountered each other in Oklahoma. According to that version of the legend, Starr was trying to take Watson into custody; Watson shot her.

Watson’s killing—and the mythology that grew around it—inspired one Peter Matthiessen, novelist, co-founder of The Paris Review, CIA operative, naturalist, Buddhist, to author a three-volume, fictionalized tome about Watson and the circumstances leading to his death. (Matthiessen later compressed the story into a single work, Shadow Country).

“His legend endures,” says Miller, who once ventured out to see the remnants of Watson’s home. “People are obsessed with him.”

The oldest pirate?

On Panther Key in the Ten Thousand Islands lived a man nicknamed “Panther Key John,” who is believed to have escaped the sinking of Gasparilla’s ship and settled down in the ’Glades. When a Census taker came around in 1900, Gomez swore he was born in 1781. The census official claims to have done a thorough interview—and then listed his age as 119 years old.

There’s a dispute about how he died, says Lockyear, the historical museum director. He’s heard it two ways: that old John got his foot tangled in an anchor and drowned, and also that “they” killed him. “They, who?” “They” who wanted Panther Key John’s gold, naturally.

Now, what happened to the gold—if there were ever any gold—is anyone’s guess. One favorite theory: The treasure was hauled out of the islands by a pack of seaplanes that showed up after the old man’s demise.


As far as reporting tools go, nothing beats social media. We asked Facebook friends for examples of local lore, and got a whole stream from Fort Myers:

“Wasn’t there something about circus people or small people?”

“Oh … that’s a good one. It was a village of little people—supposedly across the street from the Alliance for the Arts.”

“Actually, it was a little development of houses where the Magnolia Pointe subdivision is just to the south of the Cape Coral Bridge. … Everybody knows about it. Used to call it Munchkinland…” (This last respondent had worked in the subdivision some years ago and saw the small foundations, corroborating his childhood memories.)

Local journalist Amy Bennett Williams spent a considerable amount of effort chasing this urban legend and discovered that there were indeed little red-and-white cottages on the grounds of the Braden-Sutphin Farms, a vacation retreat in present-day Magnolia Pointe founded by Al Sutphin, an ink magnate, sports promoter and showman from Cleveland.

Sutphin’s circle of acquaintances may well have included circus performers who enjoyed his Southwest Florida hospitality, but according to Williams’ reporting, there’s another likely source behind the rumor: The businessman was buddies with two “vertically challenged” men: Oscar Johnson and Pete Tyrrell, each of whom barely topped 5 feet. The men liked to visit Sutphin at his resort.

If nothing else, they gave the town a good chuckle: During the Edison Festival of Light parade one year, the duo dressed up as giant babies, wearing nothing but diapers, clutching bottles and waving at the crowd atop the Braden-Sutphin Farms float.


So take that, all you Northerners with your deep historical pride and your fancy old buildings. We’ll celebrate our own special mythology—as wild as the ’Glades and as quirky as the latest “Florida Man” meme circulating the internet.   

Gulfshore Life editorial intern Makayla Connor contributed to this story.