Sixty Years Before the Cocaine Cowboys, Miami Was the Wild West of Prohibition

Al Capone wasn't the only bootlegger who set up shop in Miami during Prohibition.
Al Capone wasn't the only bootlegger who set up shop in Miami during Prohibition.
screencaps via YouTube

Thanks to Scarface, Miami Vice, and Rakontur, everyone knows that 1980s Miami was the world capital of illegal substances. But few realize that 60 years before the Cocaine Cowboys era, another brand of underworld smugglers had already turned South Florida into the Wild West. 

At the height of Prohibition, Dade County was a rumrunning capital where insane shootouts lit up the Miami River, bootleggers flaunted their cash on the beach, and liquor flowed in on the tides. 

As historian Paul George told the Miami Herald on the 75th anniversary of Prohibition's repeal: "South Florida probably flouted Prohibition more than any other part of the country. We were called the leakiest place in the country."

Prohibition took effect January 16, 1920. The 18th Amendment, ratified the year before, prohibited the production, distribution, and sale of alcohol. Here's how the Herald's 2008 anniversary story described what came next: 

In Miami and Fort Lauderdale, [the ban on booze] ushered in 13 years of illegal drinking, gambling, prostitution, rum running, high-seas machine-gun battles, public corruption and general scorn for the law. For all the notoriety of the mobbed-up '50s, the cocaine-cowboy '80s, even the hopped-up club scene of today, it was the most protracted and pervasive period of lawlessness and debauchery this region has known. 

Prohibition was supposed to reduce crime and corruption and do away with a long list of social ills. Instead, it turned bootlegging into an empire that enriched the underworld. And South Florida — remote from national law enforcement, easily accessed from the sea — was the perfect hub for that illicit activity.

Miami "accepted the 'noble experiment' with high good humor in 1920," Patricia Buchanan wrote in a 1968 master's thesis for the University of Miami's history department.

Bootlegging was as much a natural tourist attraction as palm trees and sparkling Atlantic beaches. The Miami Herald was quick to point out that tourists should be handled with care as far as the Volstead Act was concerned. "Officers Carry Out Enforcement of Prohi Amendment in High-handed and Autocratic Manner" read a page one headline in the June 22, 1920 issue. The story explained that officials had searched the car of a teetotaler on his way to Miami for a dental convention, and the Herald warned, "This might affect tourist travel next winter." In addition the paper pointed out that the traveler "had also invested heavily in Miami real estate on previous visits."

Miami's first significant prohibition case came in the early spring of 1921 when New York millionaire, Harry S. Black, a part owner of the Flatiron Building, was arrested at the swank Royal Palm Hotel. He was charged with having anywhere from 20 to 53 cases of liquor aboard his private railroad car, the "Bayside," on a siding at Coconut Grove. The Miami Herald reported that ninety bottles were produced as Exhibit A at the trial; four members of the six-man jury tested the evidence; Mr. Black was acquitted in five minutes.


By the summer of 1923, just two and half years after Prohibition took effect, a Chicago newspaper called the Florida coast "a bootleggers paradise."

A Chicago Daily News reporter wrote that Miami was "a city where, if you need a drink and don't happen to have your own flask, all you need to do is wait in the shade of a palm tree until a resident comes along, ask him where you can find a bootlegger, and if he is not one himself, he will tell you where to go. You can buy all the whisky you want in Miami at $5 a quart."

Sixty Years Before the Cocaine Cowboys, Miami Was the Wild West of Prohibition
via Google News Archives

Shootouts in Public

As illegal bootlegging exploded in South Florida, rumrunners began playing a cat-and-mouse game with the U.S. Coast Guard. The agency was given the task of intercepting smugglers who used speedboats — many powered by 400-horsepower World War I surplus airplane engines — to carry liquor from the Bahamas to points along the coast between Dade and Broward counties. Many times, the smugglers were able evade to capture by disappearing into Miami's mangroves and canals.

But on more than one occasion, the cat-and-mouse game turned deadly.

On February 24, 1926, as the sun was setting, E.W. "Red" Shannon, "King of the Florida Smugglers," approached Miami Beach in his 30-foot boat loaded with 170 cases of liquor he'd picked up at Gun Cay, near Bimini. Shannon was spotted by the crew of a Coast Guard patrol boat just south of Star Island.

In her thesis, Buchanan recounted what happened next:

The "Goose" fled north heading for the yacht basin at [Carl Fisher's] Flamingo Hotel which faced the bay at Fifteenth Street. The rum runners refused to heave to and Coast Guardsmen opened fire as the vessel neared the docks. Hotel guests attending a tea dance rushed to witness the capture. An unconscious and critically wounded Shannon was placed on a mattress on the hotel lawn and then taken to Allison Hospital on Miami Beach where he died the following morning...

The big question from the local press was, "When were the shots fired?" The Miami Herald found witnesses who stated, "The Coast Guard fired after the men had raised their hands." The Miami News, no longer the spokesman for prohibition under S. Bobo Dean, was now owned by former Governor James M. Cox of Ohio. It said: "it is known that Shannon, Nickerson and Walther ... had their hands above their heads in token surrender when guardsmen fired on them."

As the rumrunner lay dying, many of those who had witnessed the gunfire — including Carl Fisher himself — prepared to file a protest with Washington, calling the shooting of Shannon "unjustified."

Four months after Shannon's death — June 12, 1926 — the crew of a Coast Guard patrol boat chased another rumrunner up the Miami River near the Granada Grill & Apartments at 150 SE Fourth St. "Diners Flee Shots in Rum Chase," a Miami News headline screamed.

"Guests... fled terror-stricken from their rooms and dinner tables as volley after volley of shots, fired from Coast Guard Patrol Boat 297, showered about them," the News reported.

The rumrunners escaped by darting under the Miami Avenue Bridge, which was too low for the Coast Guard boat. As Boat 297 returned down river, it "was the object of cat-calls, boos, and hisses" from a crowd of spectators that had gathered, according to a Miami Herald account.

Then, on August 5, 1926 — less than two months after the Miami River shooting — seven federal Prohibition agents, who had spent the day conducting raids on moonshine stills in the Everglades, were shot at by three men on a remote road near Homestead as the agents were heading back to Miami. The agents returned fire, killing all three, who were presumed to be moonshiners, according to news reports at the time.

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Three years later, on April 14, 1929, the Coast Guard made national headlines when the crew of one of its patrol boats fired an estimated 200 shots at a fleeing rumrunner on the Miami River. One bullet fired by the crew came within six inches of a woman who was sitting in bed in a houseboat on the river. More bullets were "sprayed... into the walls of the old Gautier Funeral home on West Flagler Street; one bullet was found on the chest of a corpse in a casket," the Herald's Fred Tasker reported in his 2008 story.

Miami Mayor E. G. Sewell was outraged and declared the shootings were "worse than a disease."

Sixty Years Before the Cocaine Cowboys, Miami Was the Wild West of Prohibition
via Google News Archives

Public Corruption

It didn't take long for public officials to get in on all the cash flowing from the illegal rum casks. In August 1925, the Associated Press reported that federal prisoners in the Dade County Jail were being secretly released at night "for the purpose of bootlegging."

Meanwhile, in Fort Lauderdale, booze was so plentiful that the city picked up the nickname that sticks to this day: "Fort Liquordale."

In 1927, Prohibition agents arrested dozens of Broward County deputies and police officers in what the AP called "one of the biggest liquor conspiracies and supply bases in the country."

By 1928, the king of bootlegging himself had moved to Miami Beach: Al Capone paid $40,000 for an estate on Palm Island, where he could avoid the mounting heat in Chicago. When residents passed a resolution to force him out, the mayor refused to enforce it, saying he was "no worse than a lot of others down here."

Sixty Years Before the Cocaine Cowboys, Miami Was the Wild West of Prohibition
via Google News Archives

Violent Public Retaliation

On August 17, 1929, the war on rumrunning took a deadly serious turn when rumrunner James Horace Alderman was hanged in a seaplane hangar at the Coast Guard base in Fort Lauderdale.

Alderman had been sentenced to death for killing two Coast Guard officers during a bloody high-seas gun battle two years earlier. Alderman's death sentence was the first meted out in the war on booze and was the first execution in Broward County's history.

But South Floridians were becoming increasingly frustrated with Prohibition and what they saw as an intrusion into their God-given right to get wasted.

That annoyance was evident the night of April 7, 1932, when five Prohibition agents were met with "a display of hostility" as they attempted to raid a Miami Beach restaurant. The Miami News reported that the agents, fearing for their safety, barricaded themselves inside the restaurant and telephoned for help. Meanwhile, patrons outside slashed the tires of the agents' car and threatened to overturn it.

Then, on December 5, 1933 — 13 years, 10 months, and 19 days after it began — Prohibition ended.

In the 2011 PBS documentary Prohibition, Daniel Okrent, author of the book Last Call: The Rise and Fall of Prohibition, asked rhetorically: "How the hell did that happen? How does a freedom-loving people, a nation that's built on individual rights and liberties, decide in one kind of crazed moment... that we can tell people how to live their lives?"


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