07/16/2026
Great post about Naples past! Thanks Phil!
In April 2025, a house on Gordon Drive in Port Royal sold for $133 million, the most expensive home sale in the country that year. It was part of one deal covering three parcels of the same street that closed together for $225 million, the second-highest residential sale in the history of the United States.
You already know Port Royal, or you know the idea of it. The most expensive ground in Florida. Yachts behind the houses, gates at the streets, a name that means money.
Here is what almost nobody knows. Every foot of it was mangrove swamp worth seventy-five dollars an acre, underwater twice a day, and one man turned it into Port Royal. His name was John Glen Sample, and the picture above is the only known photograph of him. It ran once, in a trade magazine, in 1962, and then sat out of sight for sixty years. You will not find it in any history of Port Royal, because the history of Port Royal has never really been told. There is only the man in the photograph, seventy years old, walking his own lawn past a hand-painted sign that reads PIRATES' LANDING.
This is who he was, and how he made Port Royal.
SIX FEET
South of the little resort town of Naples, the land ran down to Gordon Pass in red mangrove and oyster bar and tidal creek, and the Gulf of Mexico came up over it and fell back twice a day. The largest creek was called Grand Dad Creek. The tide rose about two feet and returned, on the same schedule it had kept for as long as there had been a coast there to keep it.
Most of what gets written about Port Royal calls this a swamp nobody wanted, then reaches for the great Florida drainage story: Hamilton Disston buying four million acres in 1881, the dredges pushing into the Everglades, the hundred-year campaign to dry the peninsula out. That is a story about different ground. The Everglades is fresh water, eighty miles inland. Sample's land was salt, and nobody had ever tried to drain the south end of Naples for the same reason nobody had tried to drain the sea. The water came in on a timetable, and the timetable was the Gulf.
The problem was six feet.
That number comes from a courtroom. In 1958 the United States Tax Court heard a case about Aqualane Shores, the subdivision immediately north of Port Royal, and to decide it the court set down in sworn findings exactly what the developers were doing out in the mud. Below an elevation of six feet, the court found, the land could not be used for houses. And there was no high ground anywhere near Naples to haul fill from.
That left one place to get the dirt.
The court described it. You dredge a canal, and the spoil you pull out you pump onto the land beside it, and the land rises above six feet and becomes buildable. When you finish, the canal has filled with water, the water reaches the Gulf, and the ground you just raised is sitting on the edge of it. Every cubic yard does two jobs. It lifts the land, and it makes the waterfront. The hole you dig is the view you sell. A man who owned two square miles of tidal marsh and a dredge owned as much waterfront as he had patience for.
THE METHOD
Sample invented none of this, and the Tax Court said as much in the same findings: the method was new to south and west Florida, though it had been done on the east coast. Carl Fisher had been pumping the bottom of Biscayne Bay over the Miami Beach mangroves since about 1912 and made two hundred blocks of city out of it. In 1920 a Fort Lauderdale man named Charles Rodes cut parallel canals into a marsh and piled the spoil between them into fingers, so that worthless interior became a row of peninsulas with water on both sides. That is Port Royal's exact geometry, thirty years early. The Walker family was doing the same thing at Aqualane Shores, next door, while Sample watched.
So the honest thing to say about John Glen Sample and his method is that he took it from other men. He was a Chicago advertising man in his fifties who had spent thirty years watching other people's ideas and deciding which would sell. He looked at the south end of Naples, and at what the Walkers were doing across the line, and he understood the arithmetic. What he brought to it was scale, patience, and a salesman's grasp of scarcity.
THE ADMAN
The salesman is the part worth understanding, because it is the reason he could afford the swamp.
Sample was born in Lutesville, Missouri, in 1891, took a degree at a small Missouri college, and got his start at an advertising agency in Kansas City, where they handed him a mail-order advertisement for a hog oiler. A hog oiler is a device a farmer keeps in the pen for his animals to rub against, so the oil goes on and the lice come off. Sample wrote the ad and it did not sell. His manager pointed out that he had left the price out. He put the price in and it worked. He told that story for the rest of his life. A farmer will not buy a thing without knowing what it costs, and everything Sample did afterward came from taking that seriously.
He moved to Chicago, sold advertising space in the Saturday Evening Post, and in 1923 opened an agency with a man named Hill Blackett. Then he changed the shape of the American afternoon. Handed a laundry soap called Oxydol that four agencies had already failed to move, he put it on daytime radio inside stories built to hold an audience between the commercials. Out came Betty and Bob, then Ma Perkins, then a flood of them. To show Procter and Gamble what daytime radio could do, he once offered a packet of zinnia seeds for a dime on the air, drew something like a million dimes, and walked the company's executives across an office floor covered in the response letters. At its height the agency billed more than fifty million dollars, ran forty-five radio shows, owned most of them outright, and wrote the programs and the advertisements inside them. Millions of women knew Ma Perkins the way you know a neighbor, and Ma Perkins was a script a man in Illinois had commissioned to sell them soap.
Sample was clear about why he did it. He went into advertising, he said, because it was the fastest way to make money with no capital of his own, that was the only reason he was ever in it, and when he had enough he got out. He got out in 1948 and went to Florida.
TWO SQUARE MILES
He had first seen Naples in 1938, on a fishing trip down the Tamiami Trail, and bought nothing. The buying came later, in the middle 1940s. While he was still running the agency and serving a Navy hitch in the Pacific, he quietly assembled two square miles of saltwater marsh at the bottom of a small town on the far coast of Florida. He paid seventy-five dollars an acre. Beach frontage ran twenty dollars a foot.
Then he ran the dredges for five years. The pumping deepened the channels and raised the land, he laid roads across it at fifty-five thousand dollars a mile, and he paid for every street and sewer himself. More than three million dollars of his own money went into the ground before it returned him a cent. He hired the St. Louis planning firm Harland Bartholomew and Associates to lay out the community, gave the streets pirate names like Rum Row, Spyglass Lane, Buccaneers' Bay, and Treasure Cove, and set aside a one-acre park for Admiral Lord Horatio Nelson. He toured the place in a Rolls-Royce, kept a yacht called the Privateer, and stocked a cabinet of Cuban ci**rs he had laid in before the embargo, because he had seen it coming.
And he chose the people. Sample called himself the "benevolent dictator" of Port Royal, and he meant it plainly. He approved every buyer and every house plan himself, and before anyone could purchase a lot he had to be admitted to the Port Royal Beach Club first. Once enough homes were built, he said, he would turn the screening over to a special committee, and "then it will be a true democracy."
THE WAIT
Here is the part the brochures leave out. The adman who sold the country its soap spent more than a decade unable to sell his own neighborhood. Lots that went on the market in 1950 at seventy-five hundred dollars sat. By one history of the development, not a single lot sold in the whole of 1958. In 1962 he was still running a one-third-off sale to move them, and when the reporter from Advertising Age found him, fourteen years into the project, Sample admitted he had not yet got his money out of it. He thought he might in a few more years, and said that even if he never did, the work had been worth it, because what he had wanted was to build a good place to live.
WHAT IT COST
The lots eventually sold. A single one of them now goes for more than Sample spent to build the whole place. The method that made it has since been closed off. The federal wetlands rules that came in through the late 1960s and 1970s put dredge-and-fill of coastal marsh under a permit system a project like Port Royal could not clear today. The two square miles Sample pumped up out of the bay are the only two square miles that will ever exist, and that is a large part of why a house on them sells for $133 million.
The bay paid for them. A 2006 study of Naples Bay, prepared for the regional water district and the Conservancy of Southwest Florida, measured what the dredging cost the water. The bay lost more than nine-tenths of its seagrass and better than four-fifths of its oyster habitat, and the mangrove that once fringed about two-fifths of the shoreline was down to roughly one-tenth. Grand Dad Creek, with its oyster bars, is under the seawalls now. The bay is larger than it used to be and emptier than it used to be.
THE MAN WITH NO CAMPAIGN
Sample died in 1971. He is buried in Minneapolis, which nobody has fully explained, and he left almost no mark of himself on the place he made. The people living in Port Royal today have largely stopped knowing his name. The streets are still Rum Row and Spyglass Lane. Admiral Nelson still has his acre.
This is the part he might have appreciated, because being known was his trade and he understood exactly how it is made. He made Ma Perkins known, and Gold Medal flour, and Oxydol. He placed his advertisements where his buyers were already reading. He hired the best planners and architects, and for the Port Royal Beach Club he hired some of the best architectural photographers in the country, whose pictures of his development sit today in the Library of Congress, catalogued and free, his name in the client field, where they have waited years for anyone to look. The one product John Glen Sample never ran the campaign for was himself.
The photograph above is the only known picture of him, from a single trade profile in 1962. He is seventy, on his own lawn, walking past a hand-painted sign that reads PIRATES' LANDING, with a new yacht on order. Asked what his legacy would be, he said no monuments would be raised for his years in advertising or for building Port Royal, that both had been fun, and that he would not change a thing.
He was right about the monuments.
Six feet under all of it, holding up the most expensive ground in America, is the bay. Dredged out, pumped up, dried, and sold one cubic yard at a time by a man from Lutesville, Missouri, who learned everything he needed to know about the American public from a hog oiler he could not sell until he told them what it cost.
