History That Doesn't Suck - 158: Prohibition - So You Wanna Be a Rum Runner?

Episode Date: June 17, 2024

“You’re Bill McCoy.” “Never heard of him.” This is the story of a crazy decade-plus when America outlawed booze…but the liquor kept flowing.  The Prohibition era marks a partial return to the Golden Age of Piracy, with bootleggers frequenting old haunts in the Caribbean, including Nassau, capital of The Bahamas. These sailors are also buying, selling, and drinking copious amounts of—you guessed it—rum. But how does all this booze get from the Bahamas to speakeasies in New York?  William “Bill” McCoy is a legendary rumrunner, one of the best. He’ll be our captain as we explore Nassau’s offerings, buy from the Bootleg Queen of The Bahamas, Gertrude “Cleo” Lythgoe and set out on a 1923 voyage up “Rum Row” to New York, carefully avoiding the actual pirates and the US Coast Guard. Once we square away a buyer, we’ll take our haul to shore with Maisie Manders and enjoy a few well-earned drinks in Manhattan. All aboard!  Connect with us on HTDSpodcast.com and go deep into episode bibliographies and book recommendations join discussions in our Facebook community get news and discounts from The HTDS Gazette  come see a live show get HTDS merch or become an HTDS premium member for bonus episodes and other perks. HTDS is part of the Airwave Media Network.  Interested in advertising on the History That Doesn't Suck? Email us at [e-mail] Learn more about your ad choices. Visit megaphone.fm/adchoices

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That's because across its three GTA campuses, York U's programs are strategically designed to prepare you for a meaningful career and long-term success. Join us in creating positive change at yorku.ca slash write the future. Welcome to History That Doesn't Suck. I'm your professor, Greg Jackson, and as in the classroom, my goal here is to make rigorously researched history come to life as your storyteller. Each episode is the result of laborious research with no agenda other than making the past come to life as you learn. If you'd like to help support this work, receive ad-free episodes, bonus content, and other exclusive perks, I invite you to join the HTDS membership program. Sign up for a seven-day free trial today at htdspodcast.com

slash membership, or click the link in the episode notes. It's a murky Sunday afternoon, November 25th, 1923. We're aboard the swift, 127-foot-long British schooner, known, at least for the moment, as the Tomoka. Right now, she's lying at anchor some distance from the New Jersey coast. What distance exactly, I can't say, but it's more than three miles, which places us in international waters, and that crucial detail is the whole point. Tell you what, you take in that blue horizon, and I'll explain. These waters off the United States' eastern seaboard, yet beyond U.S. jurisdiction, are

known as Rum Row. It began a few years ago, shortly after U.S. prohibition took effect in January 1920, and it works like this. Ships carrying liquor, such as Caribbean rum, but including other liquors, some even from Canada, drop anchor in these decidedly not American waters. Small East Coast vessels then sail out and buy their booze of choice.

Now, once those smaller vessels return to U.S. waters, they will be violating the law. But the captains of these small, nimble watercrafts know where to hide to avoid the U.S. Coast Guard. Besides, what happens to them is of little concern to the rum runners. They're heading back to the Caribbean for the next lucrative haul. In fact, one could argue that they aren't even violating US law. American authorities would beg to differ, of course, but that's William Bill McCoy's take. Ah, yes, Bill McCoy,

a handsome, well-built American in his early 40s. Bill and his brother Ben used to build high-end yachts in Florida. But when their world came crashing down about the same time that Prohibition began, they turned to the rum run. In fact, despite being a teetotaler himself, Bill is credited with inventing the rum run. The New York Times calls him the, quote, chief of the West Indian liquor runners, close quote. Oh, and by the way, the ship we're on, the Tomoka, it's his.

Right now, we're waiting on a buyer interested in our last 150 cases of Bacardi. But wait, what is that vessel approaching now? Let's check it out. Suddenly, a white ship, a schooner with two masts and one smokestack, emerges from the fog. It's a Coast Guard vessel, the Seneca. A voice calls out to us across the waters. Tomoka, ahoy! I'm sending an officer to examine your papers. Hmm. Bill doesn't like this, but it's fine.

He's flying under the Union Jack and in international waters. Probably better to cooperate. He'll allow it. Accompanied by half a dozen men in a rowboat, Lieutenant Lewis W. Perkins soon crosses the relatively calm waters between the Seneca and the Tomoka. He clambers over the side and onto the deck. His men, each wearing a Colt pistol at the hip, begin to follow.

Bill calls out, Two on board is enough. The lieutenant contradicts him. All aboard. Lieutenant, you're going for a ride then. Bill then turns to his man at the helm and hollers, Full speed to sea, Captain. The swift, run-running Tomoka shoots out into the open

sea. The Seneca fires a warning shot. Bill merely laughs. He refuses to be bullied in international waters. Besides, the Coast Guard won't dare to hit him, not with their own men on board. And now, as the far slower Seneca fades to about a speck on the horizon, the infamous rum runner takes Lieutenant Lowe for a chat. Staying as calm as possible, Bill asks, Just what did you want, Lieutenant? In a likewise calm tone, the Coast Guard officer replies, I want to look at your papers.

To this, Bill readily agrees. He knows all is in order. But the lieutenant insists that something is off. He turns to Bill and instructs him to return to Sandy Hook. Bill sees right through the ploy. He answers sternly, No. Lieutenant Perkins snaps.

You're Bill McCoy. Never heard of him. Well, he's on this ship somewhere. The lieutenant questions Bill's crew, only to hear time and again that they've never heard of one Bill McCoy. Losing patience, Lieutenant Perkins orders his men to draw their guns. Bill does the same with his crew. The Coast Guardsmen and Rum Runners stare down the barrels of each other's weapons.

Meanwhile, the Tomoka continues its course out to sea. The lieutenant demands, where's Bill McCoy? Bill comes clean. I'm McCoy. I thought so. McCoy, you're making a big mistake. The only reason you're still here is that you're my countrymen. If you'd been anything but Americans, you would all be overside by now. Be sensible. If the government hasn't anything on you now, it will if you try to kidnap us. And we won't be kidnapped without a fight. Heave her to, McCoy, and I'm advising you for your own good. Bill takes his point.

Everyone holsters their guns, and they wait for the Seneca to catch up. The lieutenant and his men then row back to their ship. Things are quiet for a moment. It seems that the Coast Guard is unsure of what to do. But finally, the Seneca's captain calls out, You will follow me into harbor. If you do not, I shall fire one shot across your bows and then proceed to sink you by gunfire.

Understand? Bill acknowledges the captain, agreeing. But then he turns to his crew. Boys, I think he's bluffing. It's jail or open sea. It's up to you. There's no discussion needed. They'll run for it. Both schooners turn toward the U.S. coast. But Bill watches the wind and takes note of a transatlantic liner heading their way. Ah, the Coast Guard can't risk hitting that ship. Here's Bill's opportunity. He yells out, Let her go off and hoist the jib!

The wheel spins, the masts catch the wind. This is working! But the Seneca is coming about as well. And then comes the boom and the flash. Bill's crew works the main sail as the Coast Guard continues to fire. Each shell is closer than the last. The fourth misses by only 10 feet.

According to some accounts, the rum runners return fire with machine guns. Perhaps true, perhaps not, but either way, Bill soon accepts reality. The Coast Guard captain wasn't bluffing. With tears in his eyes, Bill orders the jib run down, fully aware that his rum running days are over. Welcome to History That Doesn't Suck. I'm your professor, Greg Jackson, and I'd like to tell you a story. So ends the bootlegging career of the most iconic of rum runners, the infamous Bill McCoy. It's estimated that he ran 175,000 cases of hard liquor. His was a short but nonetheless

good run. Yes, pun intended, and although the authorities were determined to shut down such a legend, Bill does all right. In 1925, he's sentenced to a nine-month stretch, during which he's treated like a celebrity, even attending a prize fight with the warden. Once released from jail, he returns to his old legal profession of building boats in Florida. And with that, we now embark on our first of three episodes on the manufacture, sale, and transportation of intoxicating liquors in the United States during its 13-year experiment with prohibition. And given that opening, I'm sure it won't surprise you to hear that today's bootlegging tale is that of the East

Coast's notorious rum row. Now, personally, I can't think of a better way to learn about it than by doing. So, we're going full-on bootlegger. Together, you and I will spurn the law to run rum from the Bahamas to New York City. We'll do so in the same way that we immigrated through Ellis Island in episode 118, by using primary sources detailing actual events that happened to real people to create our own composite experience. And if we manage to do this without getting caught, well, maybe we'll celebrate our ill-gained wealth with some illegal drinks at one of New York City's most famous speakeasies. Naturally, we'll want to learn the smuggling craft from a

pro, and I can't think of a better one than the rum-running king, the real McCoy himself, Bill McCoy. P.S., Bill claims to be the origin of the term real McCoy, but that's a lie. The phrase already existed. Don't let him convince you otherwise. Now, we know he gets caught in November 1923. So for our composite, we'll want to meet up with Bill a bit before that. We'll sail in the summer of 1923. So, ready to turn smuggler?

Excellent. Then let's head to the Bahamas and turn back the clock several months. Rewind. The early 1920s U.S. government has a serious law enforcement problem. Turns out that welcoming the new decade with an 18th constitutional amendment banning, quote, the manufacture, sale, or transportation of intoxicating liquors within the importation thereof into or the exportation thereof from the United States, close quote, and following it up with underfunded enforcement through the Volstead Act hasn't convinced Americans to give up the drink. To quote the British soldier-turned-bootlegger Eric Sherbrooke Walker, or James Barbican to use

his pseudonym, the Americans as a nation are determined to have hard liquor. That is thrilling news for some down-on-their-luck adventurers with the willingness to bend a few rules like you and me. I mean, the job market's still rough since the end of the war to end all wars, and now in 1923, we could both use work and a drink. So why not solve our financial problems and wet our whistles while taking a page out of our favorite book about Blackbeard and become pirates in our own right? And a reference to the golden age of piracy is spot on because the modern-day pirates that are rum runners

do a lot of business among the same age of piracy is spot on because the modern day pirates that are rum runners do a lot of business among the same group of islands that those early 18th century pirates used. The Caribbean's, no wait, let's be a bit more technical, the West Indies, Bahama Islands. A longtime British colony that often struggles financially, the Bahamas are booming thanks to American prohibition. 10 million quarts of liquor travel through the Bahamas are booming thanks to American prohibition. 10 million quarts of liquor travel through the Bahamas per year. Yet, this boom is a mixed blessing, according to local historians. It's drawn a mostly drunk and rough crowd of foreigners. They're, uh, well, you'll see what I mean now that we've joined the Tomoka's crew and are sailing with the crowned

king of rum running, Bill McCoy. We'll experience it firsthand as we stop in to load up our ship with illicit cargo. It's a beautiful evening in the Bahama capital, and once pirate capital, of Nassau, New Providence Island. We've just left the Tomoka line at anchor in the harbor, and now we're with our rum-running legend of a skipper, Bill McCoy, and a few other crew members walking down Frederick Street. Then Bill stops as we reach an eight-foot-tall wall. He opens the gate and leads us into a courtyard filled with royal palms, coconut palms, colorful croton bushes, and bougainvillea and hibiscus flowers, all of which sit in the shade cast by one massive tree in this space's center.

There's also a pelican. Locals call it Nebuchadnezzar. And behind all of this is a white, wooden, three-story building that seems to go on endlessly with its verandas and 50 or so rooms. This is the bootleggers headquarters of Nassau, the Lucerne Hotel. We ascend a winding stairway up to the front entrance. Once there, a five-foot, barely hundred-pound elderly woman, a New England transplant with gray hair and gold-rimmed spectacles, greets us. This is the Lucerne's proprietress, known only as Mother. She's basically the only person in Nassau who has any control over her guests, the bootleggers.

Mother insists that, quote, Though maybe they were just the least bit wild, they were all good boys at heart. Close quote. That's one take. Let's see what you think. Walking into the bar room, we soon see why the Nassau Tribune refers to the goings-on here as, and I quote, the orgy of the Lucerne. The whoops, yells, off-key seeking, breaking glasses, and fists slamming on tables, all make quite the commotion. We make our way to the bar to get a drink. Glancing to the side, we notice the man next to us is paying in a not-yet-discontinued $1,000 bill.

Oddly appropriate here in the West Indies, considering that West Indies-born Alexander Hamilton's face graces the U.S. currency. But seriously, who even carries that? Even more incredible, though, is that our Cockney bartender, a gent named Tommy, has enough to make change. Wow, clearly, Nassau has plenty of people flush with cash. Looks like this bootlegging thing is working out for them. Suddenly, a voice yelps in pain. A fight's broken out. Tommy dives under the mahogany-barriered countertop. Meanwhile, those who are spooked dart out of the Lucerne into the cool Nassau night. We probably should have gone with them. The noise has awakened Mother. She enters with a sigh and shakes her head disapprovingly

as she calls out to this room of brawling men. Now, boys, if you aren't going to behave yourselves, you'll have to get out of my bar room. Right away, understand? I'm going to shut it for the night now. If you can't behave yourselves, you can't have anything more to drink here. Everyone will have to leave. Tommy's going to close up.

With mutters of, yes, mother, this rowdy, drunken group obeys. The man who laid the initial blow grins sheepishly as he apologizes. Didn't mean to, mother. I'm sorry, mother. Everyone begins to clear out, us included. Well, that was a wild time last night. I assume you're not too hungover to remember little 100-pound Mother taking the roughest, toughest men in the West Indies to task. Bill McCoy says that's entirely normal.

According to our teetotaling, bootlegging skipper, quote, she would wade serenely into the welter of furious men, and at sight of the little black-clad figure and the sound of her dry New England voice, the war would die away. Close quote. Well, must be true then.

If anyone would know, it's Bill, the king of rum running. But enough about last night. It's time to get to today's task. Filling the Tomoka's hole with alcohol. Don't let the term run-running fool you. We and other rum runners certainly run our fair share of Caribbean rum, but we'll run any and all of the many different spirits so plentifully imported to and available in Nassau. Seriously, alcohol is everywhere. Just looking outside our Lucerne hotel window, we see local Bahamians driving donkey carts laden with liquor to ramshackle warehouses along the palm tree-lined harbor.

Shacks, houses, stables, warehouses, boathouses, and just about any structure that's along the water is now involved in bootlegging. Men move the precariously stacked cases of alcohol from the donkey carts to these buildings and from there onto rum-running ships. Even early in the morning, the police struggle to keep things orderly amid all the pandemonium. But enough talk. Let's go get our cases. We make our way to a warehouse on Market Street, to one of Bill's favorite places to procure goods. Ran by a slender, dark-featured,

35-year-old former stenographer with a brilliant mind who hails from Bowling Green, Ohio. This is Gertrude Lithgow, or Cleo, as she's come to be known in Nassau. We'll stick with Cleo, though I do love her future nickname, bootlegging queen of the Bahamas. It's a fair enough moniker, considering that Cleo's liquor, typically from the whiskey family, scotch to be specific,

ends up in the United States, yet also a touch off, since this American woman is operating in the British-governed Bahamas as a legitimate wholesale liquor agent on behalf of a UK firm. She had to consult with her lawyer, or her solicitor rather, as authorities questioned the legality of a woman in the role, but it turns out there was no law against it. She was simply the first woman ever to apply. So, Cleo got her license and overcame local rumors that she was a spy for the US. Now, she's one of the best wholesalers and the only woman in the business here. Anyhow, we're now at Cleo's warehouse. It's a curious spot, the second story of a building just above an antique store. Cleo's put in a set of stairs so we don't have to climb

up a ladder and through the window as she did when first starting, which is most welcome. The space itself is awesome. Here's how Cleo describes it. The walls are over two feet thick. The shutters for the windows and door are made of teak. The key to open the door lock is a piece of iron six inches long." I know, it almost sounds like this is the golden age of piracy. This is a vintage Nassau setup. As we check out the wares, a Florida operator, known simply as The Shake, because of his meticulous white attire, tries to convince Cleo to let him ship some of her bourbon on consignment. That is, to let him take the spirits without paying and sell them on her behalf with the percentage to come back to her later. Huh, Cleo laughs that off.

She knows better than to trust him. She'll stick with selling directly to crews and don't try to haggle. She knows her freight rates too. Those depend on weight and distance, but they run about $3 per case to Florida, $4 to New Orleans, and $6 or even $7 to New York. Good thing our captain has a strong bond with Cleo.

We get a fair deal, and enough to fill most of the Tomoka's hole. Returning to the ship with our donkey-drawn carts of various spirits, we notice the faint outline of letters that someone has painted over running across part of the bow. It reads, Arathusa. Huh, that's weird. This is the Tomoka, right? Asking around, we learn that Bill has changed the ship's name for strategic purposes. Here's the deal. Any vessel registered in the United States is subject to U.S. laws. So, right now, sailing under the stars and stripes would mean we're bound by the 18th Amendment,

which, I'll remind you, states that the, quote, sale or transportation of intoxicating liquors within, the importation thereof into, or the exportation thereof from the United States and all territory subject to the jurisdiction thereof for beverage purposes is hereby prohibited. Close quote. Ah, but there's an easy enough answer to that for us rum-running Americans. Since the Bahamas are a part of the global British empire, it isn't particularly difficult to find a Brit who can buy our ship and register it as a British vessel. We then simply buy it back from this loyal subject of King George V at the same price, minus a bit of commission, of course.

In fact, between 1921 and 1922, the number of vessels registered in the Bahamas increases nearly tenfold. So our ship isn't unique. Overhearing bits and pieces from the crew, we've surmised that our dear captain, Bill McCoy, purchased the 127-foot-long fishing schooner, Arthusa, in Gloucester, Massachusetts. And oh, does Bill love this ship. He'll never forget the first time he laid eyes on her. To quote him, she seemed to ghost into the harbor's mouth under full sail. She was an aristocrat, a thoroughbred from her keel to her trucks. The sun turned her spread of canvas golden, and my throat was tight and stiff as she came walking up the harbor like a great lady entering a room. Bill bought his aristocratic ship for 42 grand, half of her estimated value.

But alas, while re-registering her as a British vessel, it turned out that another British craft was already sailing under the name Arathusa. Thus her new name, the Tomoka. Bill also replaced her old auxiliary engine with a more condensed, faster one. This also increased the hull space to fit an additional 5,000 cases of liquor. Each trip from Nassau to Rhum Roe, like the one we're about to embark on, could make Bill up to $50,000. And we could look forward to a handsome cut, assuming everything goes well, of course.

So let's make sure our booze is packed and stored as needed to survive the waves and a possible run-in with the U.S. Coast Guard. With the hired help of local Bahamians, we set to work under the hot summer afternoon sun, moving all of our Clio-procured cases of spirits out of our carts, across the gangway, and onto our ship, the Tomoka. Each case is open. They have to be. These bottles of booze aren't packed tightly enough, as is, to survive a trip at sea.

More experienced crewmen show us how to wrap each bottle in newspaper and place them carefully in salt-filled burlap bags called hams. Both steps are crucial and serve different purposes. The newspaper prevents the glassware from bumping into each other on the at-times rough sea and shattering. We'll use a bit of straw to help with this too. Meanwhile, the salt inside the burlap bags will help in case we get stopped by the Coast Guard. In that event, we can throw our

bags of booze overboard and the salt will pull the bags down temporarily. Once the salt dissipates, the bags, or hams, should be buoyant enough to come back to the surface. We'll just have to hope that the Coast Guard is gone by then, if it comes to that. We stack each triangular, prism-shaped ham tightly together, filling the entire cargo hold. Then comes our final task, plugging the cracks between the sacks with sand just in case the waves are particularly bad one day. Both the straw and salt should also soak up any moisture in the hold.

And so, with our 5,000 cases of alcohol all stored below, the moment has come. It's time to set sail with the legendary Bill McCoy. Tomorrow, we'll depart from Nassau Harbor and head north for New York, knowing that our illicit cargo will ultimately lead us to one of two fates, our fortune or jail. Metrolinx and Crosslinx are reminding everyone to be careful as Eglinton Crosstown LRT train testing is in progress. Please be alert as trains can pass at any time on the tracks. Remember to follow all traffic signals. Be careful along our tracks and only make left turns where it's safe to do so. Be alert,

be aware, and stay safe. When Johann Rall received the letter on Christmas Day 1776, he put it away to read later. Maybe he thought it was a season's greeting and wanted to save it for the fireside. But what it actually was was a warning delivered to the Hessian colonel, letting him know that General George Washington was crossing the Delaware and would soon attack his forces. The next day, when Rawl lost the Battle of Trenton and died from two colonial Boxing Day musket balls, the letter was found, unopened in his vest pocket. As someone with 15,000 unread emails in his inbox, I feel like there's a lesson there. Oh well, this is The Constant, a history of getting things wrong.

I'm Mark Chrysler. Every episode, we look at the bad ideas, mistakes, and accidents that misshaped our world. Find us at ConstantPodcast.com or wherever you get your podcasts. The voyage from Nassau to New York Harbor is about 1,100 miles, or 950 nautical miles, for you sailors listening. My apologies to the landlubbers, but Dramamine doesn't exist yet. Keep your eyes on the horizon. It'll help you find your sea legs. We pass by or see a fair share of other rum-running ships along the way. As Bill once quipped, the route is filled with, quote, anything with a bottom that could float and a hold that could be filled with booze, close quote. That's not a bad thing for us. These waters can be dangerous and the right company can make a difference.

Take, for instance, Alistair Morey. He's a bootlegger from Glasgow, Scotland. Yes, a Glaswegian, as his fellow Scots would say. And on one particular rum run in the month of December, he made a quick stopover in Bermuda before heading up the coast. Transporting whiskey from his native Scotland, that is, Scotch, he hit a few problems. Well, a lot of problems.

Fuel pumps out of alignment, three blown joints, and more. Worse still was the weather. To quote the Glaswegian, and my generic Scottish accent, since imitating a true Glaswegian accent is both beyond my skill set and less likely for the uninitiated to understand, hell, hailstones, not like bullets. When they arrived, I made for the companion via a bullard that was a refuge halfway and got down below with no further loss of time, like nothing on earth I've ever seen before. Now, don't worry. We're sailing in the summer with much smoother, hail-free weather, but danger still lurks in the dark waters of the

Atlantic. And I'm not talking about killer sharks, though they are out there. No, our greatest threats are the U.S. Coast Guard and pirates. Even though we're on a British ship, the Coast Guard can still confiscate our cargo if we drift too close to American waters. But at the same time, sailing too far out on the open seas will leave us vulnerable to genuine pirates. As in, well-armed men who sail far beyond the reach of the law and prey upon vulnerable, rum-running ships, murder their unsuspecting crews, and make off with their cash and booze. Yeah, once again, it sounds like Prohibition has unintentionally caused a return of sorts to the golden age of piracy. Future historians will never know just how many rum-running ships will be lost at sea.

But take heart. We've now made it to the most infamous section of the East Coast's rum row. That legendary stretch of water running from Cape May, New Jersey, all the way up to Montauk Point on the northeastern tip of New York's Long Island. In fact, the most happening of spots is the southern coast of Long Island. Known as the Rendezvous, these waters are filled with rum runners, all anchored right next to each other. East coasters can hop in a speedboat, jet out to these international waters, then go from ship to ship comparing prices. It's like a floating mall, except every store and kiosk sells liquor.

And yet, none of this means we're totally safe. The Coast Guard might be too poorly funded to keep up with all of this, but its ships are still faithfully patrolling U.S. waters, trying to catch booze-selling smugglers like us. But we're a little safer than others. See, sailing with Bill McCoy has its advantages. He's got the money to outfit all of his ships with shortwave radios to communicate with potential buyers. Not only that, but Elizabeth Smith Friedman says that his encoded messages are, quote, "...more complicated and harder to decipher than any code which was used during the recent World War." Close quote.

And Elizabeth should know, across her career, she'll decode nearly 12,000 messages for the Prohibition Bureau and Coast Guard. But alas, on this trip, our ship's radio is broken. So we'll have to do as other rum runners do. We've posted handwritten signs that show the names and prices of our stock. When that doesn't work, though, we've got to get creative. Our daring captain takes the dinghy ashore to work a solution. He comes back victorious. The answer to our prayers will come from the heavens.

As evening approaches, a small one person biplane streams overhead. Looking up, you catch a glimpse of a falling object. What could that possibly be bobbing along the surface of the water the object appears to be an inflated old model T inner tube the captain reels it in the whole crew comes to a halt watching as it's hoisted to the deck yeah it's an inner tube all right but it has something more tied to it a golden syrup tin looking more closely we can see that something that resembles vaseline was smeared around the edges to make the

tin water typed with the airplane still circling overhead the captain opens the tin and finds a letter he unfolds it and reads mark it better off pinn Point. Will you move there at once to a point 10 miles northwest from the lighthouse? If yes, we are to wave a red cloth from the bow. If no, we are to wave it from the stern. Knowing that the city's speakeasies are desperate for our Nassau-based booze, we choose not to move. Instead, staying as close to Manhattan as possible. A man is sent to the back of the ship, where he holds up the red cloth,

allowing it to flutter visibly in the wind. But there's a second question on the paper as well. Again, the captain reads, Will you lower the price of scotch $1 as the market is falling and it is impossible to sell at the present price? The yes or no instructions are the same, except that we are to use a white cloth this time, so the pilot can be sure which question we're answering. Well, our expert rum-running skipper

isn't one to ignore market forces. This will be a yes. A man is sent to wave a white cloth from the bow. Satisfied that both questions have been answered, the airplane tips its wings and heads back toward the shore. Let's hope the pilot has enough connections to steer potential buyers to our ship. Aviators are playing a part in the alcohol smuggling game all over the country, including right here on Rum Row.

Former World War I bombers who once fought for their country against the Kaiser are now gladly dropping notes for bootleggers along the coastline. These pilots likely all have day jobs. Airmail pilots, barnstormers, some are even in the military. But it's just so hard to say no when they can make upward of $2,000 for a single flight. Not a bad payday for circling over the coastline and taking that information back to buyers,

who will take the real risk of speeding out across the waters in their boats. Okay, it's not always that simple. Sometimes, pilots in seaplanes, that is, aircraft capable of landing on and taking off from the water, will run the booze itself back to land. This is quite rare, but it happens, and right now, in the early 1920s, we smugglers have the advantage. The Coast Guard's request for a seaplane was denied, meaning that we command the air. But again, don't discount the Coast Guard. Its ships can still shoot down a seaplane or even capture one while at anchor. This hasn't happened yet in 1923, but the New York Times will report on a

Rum Row plane getting captured in August 1924 and on a Coast Guard destroyer, the Mojave, making a prize of a Rum Row seaplane on March 30th, 1925. Okay, so that's not a lot of policing success. Sounds like the odds are pretty good for aviating smugglers, which makes it hard to convince pilots that it isn't worth the risk. But again, seaplanes carrying the liquor from Rum Row is not a frequent occurrence. Normally, it's small watercraft. Our favorite British licensed distributor and fellow American back in Nassau, Cleo, made the trip to Rum Row once with Bill. What can I say? She's an adventurer, likes to live on the edge. Anyhow, Cleo says these transport boats, quote, resembled little skimming bugs with white spray wings speeding towards us on the water. Sometimes

five or six could be seen at the same time coming from their various vantage points. Some of those wee boats would make this hazardous trip for as small a load as 5, 10, 20, 50 cases. Others would take 100, 200, or 250 cases. But let's not take her word for it. We can observe this ourselves. Looks like someone is speeding our way right now. As night falls, there's still enough light for us to see a boat, likely originating from New York, closing in on our anchored position on Rum Row. Then, in the blink of an eye, two men covered in well-padded oil skins and caps climb aboard the Tomoka. They're quickly escorted into the captain's cabin so as to be as inconspicuous as possible. Well, as inconspicuous as you can be when everyone present is armed. For their own protection, of course. Ducking our heads, we follow them inside

since it's important to have as many people present for the deal as possible. We watch as the buyers are provided with an inventory of our cargo and samples of our illegal wares. Ah, if only we were allowed a sip as well. But alas, we can't. The buyers taste each of the brands that we procured from Clio and Nassau, then bicker with the captain on the price. Yeah, good luck. They won't get the better of old Bill McCoy. Finally, all is agreed to. The customers pull wads of cash out of their oil-skinned jackets, pant pockets, and from underneath their hats. With money in hand, the captain yells out the order to the ship hands on deck.

They then scurry off to get the booze. As we return to the deck, some of our fellow crew members are already tossing the carefully packed bags of bottled booze, the hams as we call them, from one man to the next. Some of the men are swearing. The hams were tricky enough for us to handle when we were leisurely loading the ship, so you can imagine what it's like when everyone is in a bit of a rush. One of the hams is rattling. Damn it. That means there's a broken bottle inside, and we're the ones who have to eat the cost. It's tossed aside for a fresh ham. We'll have to open it up and replace the bottle for the next customer later. For now, we need to keep our chain moving and get this alcohol off the Tomoka and onto the speedboat. The two crew members tasked with

keeping watch through binoculars look flustered. Perhaps there's a suspicious ship heading our way. Yes, that's precisely it. One of them yells, Cutter moving this way, break away. The ropes tying the speedboat to our ship are quickly sliced as we and our customers go in opposite directions. The buyers try to come back later in the night to finish loading. If they made it, we'd honor the sale for the sake of our reputations. But they never do, so that's a bonus for us. We'll keep the cargo and the profit. And given that outcome, the captain lets us throw back a few to celebrate such a successful sale. The next morning, as we nurse our minor hangovers, Bill McCoy tells us that he's sending us ashore.

We're heading into the city where you and I will deposit that fat stack of cash that the crew scored from last night's sail at the bank. And as rookies, the captain wants us to meet a few of his friends who can teach us about this last leg of the rum run. As we do so, we'll also take an unusual risk. We'll personally smuggle some liquor into New York City. From Fort Sumter to the Battle of Gettysburg. From the Emancipation Proclamation to Appomattox Courthouse. From the 13th, 14th, and 15th Amendments to the Compromise of 1877. From Abraham Lincoln and Ulysses S. Grant and William Tecumseh Sherman. To Jefferson Davis and Robert E. Lee and Stonewall Jackson.

The Civil War and Reconstruction was a pivotal era in American history. I'm Rich. And I'm Tracy. And we're the hosts of a podcast that takes a deep dive into that era, when a war was fought to save the Union and to free the slaves. And when the work to rebuild the nation after that war was over turned into a struggle to guarantee liberty and justice for all Americans. Look for The Civil War and Reconstruction wherever you find your podcasts. Ever wondered what it's like to be in the room with top al-Qaeda terrorists plotting their next move? Do you want to know how the history of Islamic fundamentalist thought informs the way the world works today? Well then, dear listener, Conflicted is the podcast for you. I trace the epic battles between Muslims and the West.

What are the Houthis' objectives in the Red Sea? It's a lesson to the rest of the Muslim world and the Arab world. Do not trust the Islamists. Hosted by me, Thomas Small, an author and filmmaker, and my good friend, Eamon Dean, an ex-Al Qaeda jihadi turned MI6 spy, Conflicted tells stories of the Islamic past and present to help you make sense of the world today. And now Conflicted Season 5 is being cooked up, coming to you very soon. And in the meantime, you can sign up to our Conflicted community to give you bonus episodes and access to our community hub on Discord. Subscribe to Conflicted wherever you get your podcasts. Departing late in the afternoon, we're soon zipping away from the Tomoka in our speedboat. It's about three miles and change to the landing docks in lower Manhattan.

While that's our destination, these aren't the only docks our customers frequent. Other smuggling favorites are along Brooklyn's side of the East River, directly across the Hudson River in Newark or Hoboken, New Jersey, and farther north up the Hudson to Yonkers or Kingston, New York. Those last two are tricky though. Smuggling by boat into Midtown or Northern Manhattan runs a greater risk since that's where most of the law enforcement efforts are located. But whichever docks New York bootleggers use, they will then unload their bags, that is, their hams, of alcohol from the speedboat,

place it in a truck or car, then make deliveries to warehouses, private collections, or straight-to-speakeasies. These three miles of water are a dangerous leg of the smuggling journey. But should the Coast Guard catch a gentleman or lady of the craft at this point, all smugglers know what to do. Down some hard liquor and fast. See, if you're arrested while drunk, the police can't legally interrogate you until you sober up. That buys precious time to get a lawyer down to the Customs Barge Office,

which is where the ferry terminals are, at the southernmost tip of Manhattan, to help procure bail. As you can imagine, the Customs Office hates these notoriously drunk sailors who are known to pelt reporters with hard-boiled eggs or even try to peddle their illegal wares. Thankfully, you and I won't be gulping down rum or whiskey on our speedboat this evening. We make it to Lower Manhattan's docks just fine. And as we approach our dock of choice, not far from the battery, our small speedboat crew of three, you, me, and the one man who will zip back to the Tomoka once we're done here,

catch a glimpse of a woman in the fading day's light. Dark hair, plump and in her 30s. Yes, this is the customer Bill described. This is Maisie Manders. As we pull up to a dock near the tip of Manhattan and tie off, Mazie Manders gives us a knowing look while standing next to her car. A Packard coupe with an additional leaf in the springs and large balloon tires. A gorgeous vehicle and fitting for a woman donning a fur coat and a hat with a veil that

comes down to her chin. That's a brilliant look for one who wants to hide her identity without looking like she's trying to hide her identity. You just have to get pretty close to see her brown eyes. We quickly unload the hams from the boat. As we do, Maisie opens the lid at the back of her coupe. She then tells us to open the hams and give her individual bottles. We hand them over two or three at a time as she places them in the back of the car amid layers of straw to prevent any from shattering.

Meanwhile, our no longer needed third man speeds off in the boat back to Tomoka. It takes about 45 minutes, but finally, the car is full. It holds almost 350 bottles. Grinning, Maisie slams the lid shut and locks it. Turning toward us, she says, You brush me down while I touch up my dial.

Um, what? Sensing our confusion, Maisie tells us to help dust her and the car off. We can't have anyone seeing straw peeking out of any cracks. A cop would find that too suspicious. The New York bootlegger whips out a makeup bag from next to the driver's seat and proceeds to touch herself up too. And now that she and the car look pristine, it's time to go. As all three of us jump into the coop, Maisie locks the windows and doors from the inside. She tells us, it would take a can opener to get me out of here once I am

in. When I am locked in my coop, they would have to smash up the car to get at me, and it would take a real tough guy to do that to a good-looking young lady like me, and without any evidence too. Besides, I might not wait for them to try. And with that, Maisie starts up the car and we drive off, leading the docks ahead into Manhattan. Maisie takes us a few blocks north, perhaps a mile or more, to her favorite hotel in Greenwich Village. As we grab a coffee,

she tells us that this is where we part ways. She can't let us in on her meetings with buyers. That would frighten them away. Yeah, fair enough. We part ways with the famous female smuggler and head to our room. It's time to call it a night. The next morning, we head to the bank to deposit that cash from our recent sale on Rum Row. None of it turns out to be counterfeit. Lucky for us, that's known to have happened to a few ships. Things go smoothly, so we're in and out of there pretty quickly.

Now, to be perfectly clear, the situation with Maisie, where we actually left Rum Row and brought our wares into the city for her, is quite rare. It's far more often the way our first sale went. The customers take their speedboats to us out in the Atlantic. That said, we rookies are here to learn the business, end to end. So, per Bill's instructions, it's time for us to visit one of the most popular places our customers on the water use to smuggle rum-run liquor into the city. The Fulton Fish Market. We make our way south, not far from the very docks we arrived at last night. The Brooklyn Bridge's two iconic towers loom

ever larger as we do, and then we're there. On South Seaport Street, an industrial-looking structure housing one vendor after another, known as the 10 Building, stands before us. Take a good look, because it won't be around forever. About a decade from now, in the 1930s, it will slip into the water after its pilings collapse, likely from the sheer weight of the fish unloaded here. The new building will carry on, but I trust that helps you grasp just how much fish is coming through here. Still, I digress. Located here at the mouth of the East River so that fishermen can easily deliver their catches, this fish market has been going strong since 1822. In fact, next year in 1924,

almost a quarter of the seafood sold in the US will pass through the market, as does a lot of booze. The Fulton fish market appeals to bootleggers because of its proximity to the water. Naturally, our customers making purchases from Rum Roe want to unload their catches with the same ease as any fisherman. And with so many boats and buyers moving through each day,

who's going to notice a few more? Well, I guess there is someone who will. New York Coast Guard Division Commander A.J. Henderson. Citing reports of trucks leaving the market loaded with liquor covered by a layer of fish on top, A.J. will write to Commander Charles S. Root in Washington, D.C. in 1927. In my opinion, reliable inspectors should be at Fulton Market at all times, and a rigid inspection should be made of the unloading of all fish cargos. Huh, smart man. But since we're still in 1923, that's yet to come. We feel pretty safe as we

meet up with one of Bill McCoy's associates. Bill's man walks us through the market, pointing out just how everything is hidden. For instance, he brings us over to his stall and removes a dead fish from its ice bath. Covering our noses from the smell, you wouldn't believe how potent even the open-air markets can get. We can see bottles of liquor nestled below. So glad AJ and the rest of the Coast Guard haven't caught on yet. Business at the Fulton Market is booming. Again, Maisie Manders will always get her special consideration, but operations like this is how most of our liquor will continue to make its way into New York. It's pretty efficient. Since most restaurants and the occasional speakeasy serve fish on their menus, it's not suspicious when a crate from the Fulton Market gets delivered,

even though that crate has a little more than salmon resting on the ice. Or should I say on the rocks? After all, the only thing remaining at this point is for New Yorkers to enjoy their illegal inebriating drink. We return to the Bahamas. We also move to a different crew, meaning that we don't get caught with Bill in November. We'll continue doing our Nassau-based rum running, smuggling liquor up and down the East Coast. But as the years pass by and our wallets burst at the seams, we certainly enjoy a few nights out, blowing some of that ill-gotten cash at a New York speakeasy. Now, we know that there are a slew of speakeasies on one block of West 52nd Street. 39 clubs and speakeasies by the late 1920s, to be exact. The most famous will be located at 21 West 52nd Street, run by a set of cousins,

Carl Kreindler and Charles A. Burns, better known to their friends as Jack and Charlie. Now, that location won't open until 1929, but even now, in the mid-1920s, we can still get the 21 Club experience. 52nd Street might be where Jack and Charlie settle, but they've been in business since 1922, just at a different address. Well, a few different addresses. They move around a lot at first, and currently, the club is in the booze-soaked Greenwich Village. So come on, let's check it out. It's an unspecified evening in 1925. Light pours out of the windows of countless New York City buildings as we walk up 6th Avenue. We soon come to the corner of Washington Place, turn, and start scanning

the addresses for the number 88. This isn't our first time at Jack's and Charlie's Club, but it is our first time since they moved to this address. Oh wait, that's it. Huh, sure looks ordinary. The gloomy, dingy walls give way to boarded up windows and a lot of built up coal dust. The only thing unusual is the bright, new looking beige sisal rug running down the wooden steps toward what appears to be a cellar. I'm guessing that's it. Let's find out. As we approach the old wooden door, an eye peers at us through a peephole. The eye belongs to Bill Hardy, who's yet another relation of the cousin owner's. Now, if he doesn't like the look of us, if he suspects we're revenue agents, Bill will press a button that will alarm everyone inside to start clearing out,

both themselves and the liquor. But even though it's been a while, we haven't seen him since the cousins were operating their old club, the Redhead. Bill knows our rum-running faces when he sees them. He opens the door, grins, and lets us in. Stepping inside, we find the dingy exterior jarringly contrasts the bright, meticulously styled interior of this club, called fronten. The word describes the main wall of a highly court, a sport of Basque and Spanish origins distantly related to squash, and the speakeasy is aptly decorated a la espanol. The concrete floor

is painted a deep burgundy, and white stucco walls climb to meet a low, dark-beamed ceiling. The lights are always dimmed. Tables with high-backed, dark wooden chairs and banquet seats make room for the nearly 60 people who can fit inside at any given time. Peeking around the corner of the red, orange, yellow, and black striped curtains hanging from the ceiling, we see the centerpiece of the room. The bar and its ever-so-illegal booze. The bar consists of a plank draped on top of two carved wooden sawhorses. The bartender stands

behind four pitchers filled with scotch, rye, gin, and bourbon. Since their pre-prohibition stockpile has likely long run out, the bar boasts bottles of wine and spirits that came directly through rum row. Jack and Charlie seemed to have thought of everything. They even installed a drain below the bar so that, as Charlie once said, if any trouble came, we could quickly pour the pitchers down the drain and scoot out the back through the coal cellar door and out onto 6th Avenue. If the Lucerne Hotel in Nassau was magnificent, this is otherworldly. We settle into our high-backed wooden chairs and watch as the front end fills up. The place is packed by 11pm.

The food is unreal. The menu boasts steaks, chops, sauced meats, and sandwiches, all made fresh by an Italian chef. It's no wonder we heard this establishment was nicknamed the Little Restaurant. Looking around, we hope to catch a glimpse of the famous New Yorkers who are known to frequent the Spanish-inspired, Italian-influenced club. Maybe tonight, Madame Polly Adler will walk through that great wooden door. Or evangelist Amy Simple McPherson. Remember journalist H.L. Mencken, who so blatantly criticized President Warren G. Harding's inaugural address in episode 155? Yeah, he's often here too. If only Al Capone

were visiting the city though. Rumor has it that this is his favorite haunt in New York. But you know, forget the celebs. We have steak, whiskey, and more cash than we know what to do with. This rum running business isn't so bad, as long as we continue to avoid getting caught like our old captain, of course. Ah, poor Bill. Though, as we've heard, his jail sentence sounds like a slap on the wrist. Well, I say we raise a glass to the man who never raised one himself, yet taught us the trade. Here's to the chief of the West Indian Liquor Runners,

to Bill McCoy. Cheers. Well, we did it. We became rum-running, Nassau-based smugglers. We know the swashbuckling feel of the Lucerne Hotel, Clio's impressive and ungodly stockpile of scotch and more. We braved the dangerous 950 nautical mile voyage from the Bahamas to Rum Row's busiest section a few miles out from New York City, and did so with the infamous Bill McCoy, no less. And we saw firsthand how Arbuz makes it across those last few miles of water and passed Lady Liberty to greet the lips of prohibition flaunting New Yorkers. But of course, the most pressing and interesting question in all of this is the morality, or lack thereof, in the rum-running and smuggling game. What do we make of the smugglers and gangsters? In their minds, they're heroes flouting unjust laws. Indeed,

our dear Captain Bill McCoy likes to compare himself to founding father John Hancock. That's right. In Bill's mind, he's just like this famous Boston merchant of the 1770s, a good man ignoring a bad law. If John was fighting evil taxation policies implemented under the Union Jack, Bill sees himself as fighting the evils of prohibition implemented under the Stars and Stripes. But is it the same? Does this comparison to the Declaration of Independence signing smuggler hold? I guess that's something you'll have to weigh in your own mind, both in regards to rum-running Bill and other smugglers in the

episodes to come, some of whom will be a little more willing to get their hands dirty than our dear old captain. Yes, next time we'll find it isn't just the liquor that's flowing, but blood. History That Doesn't Suck is created and hosted by me, Greg Jackson. Episode researched and written by Greg Jackson and Riley Neubauer and written by greg jackson and riley newbauer production by airship sound design by molly bach theme music composed by greg jackson arrangement and additional composition by lindsey graham airship for bibliography of all primary and secondary sources consulted in writing this episode

visit htbspodcast.com htds is supported by premium membership fans. You can join by clicking the link in the episode description. I gratitude to kind souls, providing additional funding to help us keep going. And a special thanks to our members whose monthly gift puts them at producer status. Andy Thompson,

Anthony Pizzulo, Art Lane, Beth, Chris Jansen, Bob Drazovich, Brian Goodson, Bronwyn Cohen, Carrie Beagle,

Charles and Shirley. Charlie Magis, Chloe trip, Christopher merchant, Christopher Pullman, David DeFazio, David Rifkin, Denki, Thank you. The French Revolution set Europe ablaze. It was an age of enlightenment and progress, but also of tyranny and oppression. It was an age of glory and an age of tragedy. One man stood above it all. This was an age of glory and an age of tragedy. One man stood above it all. This was the age of Napoleon. I'm Everett Rummage, host of the Age of Napoleon podcast. Join me as I examine the life and times of one of the most fascinating and enigmatic characters in modern history. Look for the Age of Napoleon wherever you find your podcasts.