Smugglers’ Coast: Everglades City’s Smuggling History

Why the Mangrove Maze Made a Perfect Smugglers’ Highway

Look at a chart of the Ten Thousand Islands and you’ll understand this whole story before you read a word of it. Thousands of mangrove keys, no two channels alike, tides that quietly rearrange the sandbars every season, and not a road in sight for miles — this backcountry has always rewarded the people who knew it and swallowed the people who didn’t. Calusa paddlers moved through this same maze centuries before European contact, and by the early 1900s it was already hiding men on the run, including the fugitives and rough characters of the Ed Watson era, when the nearest sheriff was a long boat ride to Key West. What changed over the twentieth century wasn’t the geography. It was who was using it, and what they were hauling.

Prohibition-Era Rum Running Through the Islands

When the Eighteenth Amendment shut down legal liquor in 1920, the same fishermen and boat handlers who worked these waters for a living found a new use for their local knowledge. Boats out of Everglades City, Goodland and Chokoloskee ran out past the reefs to meet supply runs relayed from the Bahamas and Cuba, then threaded cases of liquor back through passes and mangrove tunnels no Coast Guard cutter could safely follow. It wasn’t glamorous work — mostly long, wet nights poling or running low-slung boats through skinny channels only a local could read by moonlight — but it paid better than a hard season of mullet fishing, and out here enforcement was thin and slow to arrive. By the time Prohibition ended in 1933, rum running had already proven a pattern this coast would repeat twice more before the century was out: hard years on the water, a mangrove maze nobody from outside could navigate, and a cargo worth the risk.

From Stone Crabs to “Square Grouper”: the 1970s–80s Marijuana Years

Four decades later the same pattern surfaced again, this time with marijuana instead of liquor. Commercial fishing in Southwest Florida had gotten harder — tightening regulations, falling dockside prices, and a stone crab and mullet economy that couldn’t always cover a boat payment — right as offshore vessels started staging marijuana loads for smaller boats to run to shore. Watermen in Everglades City, Chokoloskee and Goodland who’d spent their whole lives reading these tides and backcountry channels found the transition easy: the same skills that put a boat on a redfish flat at low tide put a load into a hidden creek before daylight. Bales that washed ashore or got hauled aboard picked up the nickname “square grouper” — a wink at a catch that looked nothing like a fish but paid a lot more than one. It wasn’t every family, and it wasn’t universal, but in a town this small, enough people were involved that it reshaped the local economy for the better part of a decade — a chapter locals here still talk about matter-of-factly rather than pretend never happened.

Operation Everglades: The 1983 Raid

It ended in a single coordinated sweep. In July 1983, DEA agents working with Collier County and Florida authorities ran a joint operation — publicly known as Operation Everglades — that moved on Everglades City all at once, early on a single morning. By the time it wrapped, a large share of the town’s working-age men had been arrested on federal marijuana-trafficking charges. It made national news: a fishing village small enough to walk end to end in twenty minutes, with a meaningful share of its households touched by one coordinated federal case. The raid effectively ended the marijuana economy here overnight. What followed was a hard, honest rebuild — back toward stone crab, back toward legal charter fishing, and eventually toward the tourism dollars that keep this coast running today.

Totch Brown: The Story Told From the Inside

Most of this era survives only as rumor, court records and old newspaper clippings — except for one voice who put it in writing himself. Loren “Totch” Brown, a Chokoloskee-born fisherman, alligator hunter and lifelong gladesman, wrote candidly in his memoir Totch: A Life in the Everglades about hauling marijuana through these same backcountry channels during these same years. That kind of first-person honesty is rare in a story this easy to romanticize or bury, and it’s what makes his account the single best window into how ordinary working watermen actually experienced these decades. Read the fuller arc of his life, from gator hunting to gladesman to author, on our Totch Brown page.

Running the Maze Today — Legally

Here’s the good news: every channel in this story is still out there, and you can still run it — just with a USCG-licensed captain instead of a lookout watching for patrol boats. The same passes that hid rum boats and marijuana loads now carry private charters and fishing charters full of families who just want to see the backcountry, legally and in daylight. Our captains grew up on this water the honest way, and they can point out the kind of hidden creek that made Operation Everglades necessary in the first place, or the stretch of water where a rum runner would have cut his engine to drift past on a falling tide. If this coast’s outlaw history has your attention, the rest of its documented past — the Calusa, the hurricanes, the company towns — is waiting on our Local History hub. The smuggling years are done. The maze isn’t, and it’s a lot better seen from the deck of a boat than from a courtroom transcript.