All Episodes

December 16, 2021 27 mins

How do you smuggle alcohol into the country during Prohibition? Being well connected, great management skills, strong interpersonal relationships, and having a passion for the industry. While that sounds like a born Linkedin profile bio, Helen and Matt learn that being a Rum Runner was at times both thrilling and boring, yet almost always lucrative. 

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
This is job Selete, where we talk about jobs you
just don't see anymore. This week we're looking at an
illegal job. Why was it illegal because alcohol was illegal? Yikes.
And while you're probably more likely familiar with the term bootlegger,
we are looking specifically at smuggling booze over water. So

(00:20):
let's dive into the seas as we learn about rum runners, Prohibition,
watered down booze, fleeing the coast Guard, sunken hand, the bootleg,
Queen of the Bahamas, and the birth of the Weekend. Helen,

(00:42):
how familiar are you with prohibition? The Prohibition that's when
the United States government thought that it would be better
for US Americans to just not drink, and we Americans
in true form, were like, nope, we're drinking. Oh yeah,
So yeah, we're talking about the Eighteenth Amendment, which prohibited

(01:04):
the manufacture the transportation of alcohol, which is one of
America's favorite pastimes. And so of course Americans continue to drink.
They still got their alcohol, and one of the ways
they got their alcohol was by boat from Cuba. They
shipped it illegally. Yeah, so that's the episode today, we're

(01:25):
talking about rum running. The people on the boat were
called rum runners, and it applies to smuggling alcohol over water,
as opposed to bootlegging, which is usually applied to smuggling
alcohol over land. Ah, that is very interesting. I did
not know that there was a different definition for people
who smuggled over different types of geography. So bootlegging is

(01:49):
if you were like in a truck and running alcohol around,
but rum running is if you're on a boat. Someday
there will be a a word for every specific little
thing possible, I promise. Yeah, we have another audience question today. Hi,
my name is Alicia, and I wanted to know about
rum runners. If they were caught, what kind of punishment

(02:12):
would they likely to get. That's a great question, Alicia,
I too am curious. Did they get caned publicly in
a square? Were they forced to drink everything that they
were smuggling? Because that wouldn't be too bad. In fact,
I don't think many of the rum runners were really
that afraid. And we're going to get into that later
in the show, so stick around. But right now it's
time to hop into that time machine. You got that, ready, Helen? Yes,

(02:34):
the jobs a lead time machine. Are you guys ready? Yeah,
So we're back in Prohibition, that's the nineteen twenties, and
we have an expert with us who knows a lot
about this time, a lot about the smuggling between Cuba
and Florida. That's right. Our expert today is Lisa Linquist Door,

(02:56):
a professor of history at the University of Alabama and
author of A Thousand Thirsty Beaches Smuggling alcohol from Cuba
to the South during Prohibition. Let's go ahead and look
at the qualifications of rum runners. First of all, there
are a couple of things you needed. You probably needed

(03:17):
a boat, and the folks in Cuba said that you
could get a boat that could smuggle about eight thousand
cases of alcohol per trip for about eight thousand dollars.
So it might take some initial capital you would need
to go. If you were running from Cuba, you would
need to be able to purchase your liquor, so you
would need some capital that way. But you also needed

(03:37):
a relationship with a wholesaler. This would be a person
in Cuba who not only would provide you with all
of the various sorts of alcohol that you might want
to have in your illegal cargo, but that also they
could provide you with all of the shipping papers that
you would need to be able to appear to be
running a legal operation. That is interesting. So if you

(04:00):
wanted to be a full time profession rum runner, you
needed to have the boat, and you needed enough cash
to buy the liquor when you got to Cuba. But
then there were people like, Oh, I've got a boat
and I'm about to go to Florida. Why don't I
just try to sell a couple of cases while I'm here. Folks,
it is not easy being a criminal. You have to

(04:21):
be an entrepreneur. Everything she was describing is okay. This
sounds like you're just a small business owner and you're
you have to get all these hookups, connections, capital, and
it's a lot of work you needed to I was
the whole time she was saying like you needed to
have a relationship with the wholesaler. I was literally imagining,
you've got to know Captain McCarty or Captain Morgan. You've

(04:46):
got to know Captain Morgan or Mr baccarty and be like, hey,
Mr baccarty, throw some cases in the boat because I'm
about to go ahead to Florida and distribute them in
the US. Yeah, if you don't know who's querro. You
gotta go beyond that. But yeah, so entrepreneurship, I think
that I would add that you had to be bold,

(05:06):
no fear of getting caught, because it does take a
certain type of person to take this much of a risk.
And I think also something I would add is passionate
about the industry. And we're going to see that with
one of the rum runners we look at later. Yeah,
I mean, you probably couldn't do this job if you
were puritanical in any way, or if you were, like

(05:29):
not someone who thought alcohol should be distributed. It reminds
me of before marijuana became legal in California where I live,
and is it's still illegal in a lot of places
in the United States, probably most places in the United States.
I have to admit I did partake in the illegal,
the illegal acquisition of marijuana, and it sounds very similar.

(05:52):
That type of person sounds very similar. It's like they
were very entrepreneurial. They had they had to buy the
weed from a wholesaler to then sell it to some
small batch just to someone like me, and and they
had to be think quick on their feet and not
get caught. Historically, rum runners were often also pirates, and
so I think, as with any illegal occupation, you're going

(06:15):
to have rough characters and you're going to have just
the potential for violence. Perhaps was it helpful to have
a hook as a hand, Yes, oh definitely, But yeah,
let's look at the skills now. Once you're actually in
that position, there's just so much you have to worry about.

(06:37):
When Americans thought about rum runners, they were a very
romantic figure during prohibition. However, other rum runners said, no,
what you really need to be is a cool, logically
minded businessman of how you were going to locate your supply,
figure out where you were going to deliver it, and
handle the business along the way. Ideally, you needed to

(06:58):
be able to create a relation ship with say some
drivers on the coast, so that they would be able
to distribute your cargo once it got there, and you
would need to be able to locate a crew and
recruit a crew and be able to keep them long
enough to finish your voyage. Oftentimes, it wasn't uncommon for
seamen to disappear every time the boat stopped at a dock,

(07:20):
so you needed to be able to to put together
that amount of an operation and again maintain your business
relationships and handle the finances from purchasing your cargo with
the wholesaler all the way to getting your pay once
you had distributed it on the on the coast, and
so it was much less about being sort of a
swashbuckling pirate rather than being a consistent businessman. It would

(07:42):
also be useful for you to know the shoreline in
case you have to outrun a coastguard. If you have
taken a load off of a schooner that's anchored out
outside territorial waters, you need to run that back into
short if the coastguard catches you, you're One of the
best ways to get away with it, or to get
away from the coastguard is to be able to go
into shallow waters because the coastguard probably can't follow you there.

(08:05):
So you want to know where those inlets are. You
want to know where the main grove swamps are and
so that you can zip in there and get out
of sight quickly. WHOA. She makes a really good point
that the job is boring, because when I think of
rum runners or bootleggers, it sounds exciting. You're out running
the cops and you're out running the government. Who are
trying to catch you, and you're like driving fast and

(08:27):
you have guns. And if you're a rum runner, then
you're a pirate and you might have a hook for
an arm and go r and just have a boatload
of rum. But actually you need to be a businessman
and do all the things that that a business person
would be good at, which is like distribution of your material.
Rum running more like rum sitting, Am I right? Just
like sitting around most of the time organizing boring, Yeah,

(08:51):
rum middle management. Because yeah, everything she described remind me
of the old job I used to have as a manager.
And I was like, yeah, you gotta deal with like
sailors that don't get along and then they're not showing
up for work and then they were here yesterday where
they go or they're all drunk on the boat. Come on, guys,
we gotta ship this stuff. So yeah, I think the

(09:12):
ones in charge on the boats they didn't have a
glamorous life at all. Professor Lindquist Door did mention the coastguard,
and if the coastguard did catch up to you, which
sometimes they did, usually they did not, But if they
caught up with you, there were ways to still get away.
Rum Runners would go on shore and they would bring

(09:33):
out prostitutes, and they would have prostitutes available for any
Coastguard ships that were around, hoping that by providing this entertainment,
this diversion for a Coastguard boat, that Coastguard wouldn't wrest
them or take them in. So they were all sorts
of ways that they sought to distract coastguard folks. That

(09:55):
is really interesting. I thought that she was going to say,
bribe with cash. That happened to well and and booze. Yeah, yeah,
cash and booze. You have the cash and you have
the booze. But then now you also have to get prostitutes.
And that makes more sense because if you bring out
the prostitutes and they're literally going to be busy for
at least twenty minutes, say, and the coast guard was

(10:15):
outstretched anyway, So the odds of actually running into the
Coastguard on a typical rum run we're slim anyway. But
it's we called the job rum runner, and a lot
of times it's just the fact that they knew maybe
we should call it rum navigator. Maybe that's not but

(10:37):
they knew where to go to begin with, to not
be where the coastguard were yeah, yeah, rum navigator, that's good.

(10:59):
Now we're gonna look at tools of the trade, and
I would start with saying they needed good maps, as
we mentioned earlier, to know where the coast guard would
not be. But the next tool of the trade is
I think far more interesting. One bootlegger landed nineties six
thousand bottles of liquor from Cuba in the United States.
He then took that those nineties six thousand bottles of

(11:21):
high end spirits and cut and deluded them into seven
hundred and fifty thousand bottles of bootleg booze. And so
they would add a little extra liquor, they would add
coloring and flavoring to extend their weares as it were.
So even if you were getting good what was originally
good spirits from Cuba and those European countries who were
still sending it to Cuba, that didn't necessarily mean that

(11:44):
by the time it got to the table it was
anything like that. Okay, So you would certainly need what
we would call clearance papers, and so to legally be
engaged in maritime trade, you have to have papers that
indicate that you have delivered your document, your cargo to
its appropriate destination, and in this case it would be
someplace other than the United States. Now, if you were

(12:05):
planning to unload your cargo and sell it in the
United States, what were you gonna do? So you would
have to have somebody who would forge those documents and
showed that you had delivered your document your cargo to
a legal port on Oftentimes it was a place like
Honduras that it was more than happy at the consulate
in Havana to forge those documents for you. Unexpectedly, you
would also probably need things like straw and burlap. One

(12:28):
of the problems of transporting liquor was that when you
threw them overboard because the coastguard was coming after you,
they tended to float, which meant that they could be
picked up by the coast guard and used as evidence
against you, and they could also be tricky to move.
So most rum runners sewed bottles into packages called hams
because of their shape, and they would put about six

(12:48):
bottles in pack them with straw sewed up with burlap,
and they would be easier to transport between a rum
running ship and a boat coming from shore. And helpfully,
also if you threw them overboard if you had to
jettison your cargo they sank. That is so interesting and
absolutely one hundred percent makes sense because if you're the
only thing available because it's illegal everywhere else, it's not

(13:12):
like people can be like, hey, your booze is watered down,
I'm gonna buy this other booze. Like sometimes it was
the only booze available, so you could do whatever you
want with it. You could water it down like by
half and just be like, hey, it's this or nothing.
You're drinking milk otherwise, buddy, and still make the profit. Yeah.
So I didn't even think about this. Of course they
would do this, but the fact that it went from

(13:34):
bottles of spirits to seven bottles. You know what? I
have this? I have drank watered down booze at at
a many a bar and many a club in my day,
and when it happens, I am so mad or I'm
so drunk, I'm too drunk to be mad. But if
I wasn't drunk enough to notice I was mad, Yeah, well,

(13:56):
don't get it on the rocks if it's already deluded. Man,
does this mean that there's still bottles of booze like
at the bottom of the ocean between Cuba and Florida,
I believe. So. I bet you went to the bottom
of the Mediterranean, see, they would definitely be sorry. If
you went to the bottom of the Caribbean Sea there
there would be some of these bottles, these hands, those

(14:19):
fish are drunk down there. I find that amazing the
fact Professor Linquist Door mentioned the forgery as well, So
we're talking about very specific skill sets here and very
specific tools they needed to have to make this whole
operation work that I just wouldn't have thought of otherwise.
I just assumed, no, they're just going really fast in

(14:39):
these ships trying to outrun the coast guard. But it
was very methodically. I keep thinking of the Pirates of
the Caribbean. I can you imagine Jack Sparrow, the Johnny
Depp character, like going into the Honduran consulate and be like, so,
would you mind forging a document for me in case
I get caught by the Coastguard? I could, Actually, I

(15:01):
can imagine his character doing that. I mean, it does
require a lot of connections and being good with different
types of people to get what you need. But let's
look at a typical day of a rum runner keeping
your crew attentive while you are at sea is a
key problem that you have. You certainly want to keep
enough crew so that you have a cook for example,

(15:23):
or that you can keep if you have a power
engine on your boat, that you can keep the engine
running optimally. Having gas combustion engines on boats, it could
be really tricky. So there were a number of rum
runners that actually ended their career because the engine exploded.
So you wanted to make sure you had mechanics who
could fix an engine when something happened to it, as

(15:43):
was not infrequent in anyway, you had to be able
to keep your sales in good running order to keep
your boat ship shape, and most crew members wanted and
thought it was their right to be able to sample
the cargo. So you have to make sure that you
are coming north with enough cargo to still profitable and
that your crew can do what they're supposed to do
instead of tippling too much on the inventory. You have

(16:06):
to keep an eye on the cargo otherwise it's going
to go down the throats of your staff. Yeah, that
makes sense. Taking care of the ship, taking care of
the booze. I think this is stuff that's not glamorous.
So much of this is just going back and forth
making sure everything doesn't fall apart. That's so interesting that

(16:28):
she said this is this was like in the twenties.
I guess it was the beginning of when there might
be an engine powered boat and they would light on fire. Yeah,
catch fire, and then there goes your whole boat and
your inventory. Yeah that could be bad so well, especially
the smaller boats that were a lot of these boats

(16:49):
were private. They were expensive, so if you want to
if they cheaped out on maybe a boat, it might
be a little more likely to explode. But now it's
time for our audience question finally answered. What if they
were caught. They weren't caught all that often, it was
definitely a possibility. One runners speculated that he was probably

(17:12):
caught about once for every five runs that he made,
and that he figured in the cost of that into
his cost of business. He figured that all he would
need to do he would lose his liquor and he
would have to re buy his boat back at auction,
But then he could keep going and he made enough
money that really was just not particularly problematic for him. Certainly,

(17:33):
some eventually over time will be put away in prison,
but generally for not all that long, the penalties were
fairly minimal. It might be a year in federal prison,
and so that was a risk as well. Wow, so
a year of prison time. It's yeah, I mean it's
not ideal, but it's not If you were if this

(17:54):
was your full time gig in this and you were
making a ton of money, you know it's doable. You're like,
I got caught. I did a year. It's very similar
to drug dealing today. I can already say yeah, it
could be lucrative and worth the risk. And even if
you were cut, and then back to what we were
saying earlier, you could you could maybe bribe the coast guard,

(18:17):
or there's other ways to get away. The one person
she mentioned that got caught like one out of every
five times, that was the exception. By the way, I
want to make that clear that typically most rum runners
were not worried about getting caught, and especially if you're
turning whatever she said earlier, like ninety thousand barrels into
seven hundred and fifty barrels by diluting your liquor, and

(18:41):
you're making a ton of money. Say you do get caught,
and you do have to pay all the fines and
you lose a batch of liquor and you lose your boat.
Like you're making enough money that you can make all
that back. Let's zoom out a bit here and look

(19:04):
at context. We briefly mentioned earlier that rum running had
happened for a while before prohibition. So for example, when
the American colonies didn't want to pay taxes on their booze,
they would just rely on pirates rum runners who would
sell it to them for much cheaper and skip over

(19:25):
the British taxes. So the reason why we are focusing
on prohibition for this episode, I think mostly is there's
just the special aspect to prohibition regarding American consumerism. One
of the interesting things about prohibition is I think in
some ways it brings about some pretty significant changes in

(19:45):
culture and or accelerates or put a focus on some
things that were already going on. So this is a
moment at which more Americans have a little bit more
money to spend, since there's some changes in labor and
salary practices, they have a little bit more time on
their hands. It is really the first moment when people
begin to think about consuming just for pleasure, just for

(20:06):
the fun of it, not out of a need to
keep body and soul together, to keep alive or keeping warm.
And so they are beginning to look at the ability
to buy things as a way to display their personality
and who they are. And so at the same time
that we have prohibition going into effect, we also have
Americans consuming an enormous number of new products, from powder

(20:29):
and rouge for women, to cars, to vacuum cleaners, to
all sorts of different clothing items, and buying as a
way to present yourself and to show your personality as
a new thing. Matt, is this the beginning of when
Americans had an official weekend? It is. I love to
bring this fact up recently because I learned it just recently.
But yeah, the weekend wasn't even a term that most

(20:52):
people knew about until around this time of prohibition. Isn't
that so human nature and American culture that as soon
as we invent a weekend, we're like, and we need
to drink. We're focusing on the liquor coming from Cuba.
But of course this came from all over the world,

(21:13):
like so much was smuggled across the border from Canada
and Mexico, do we know any stories of actual rum runners,
like do we have do we know of any famous
run runners? We do? Have you heard of the term
the real McCoy? Yeah, it means like the real thing, right,
that's right. The term the real McCoy actually originally referred

(21:36):
to our notable person, who is William S McCoy. I
think probably the most famous of the rum runners is
Bill McCoy. He does most of his rum running out
of the Bahamas, but he was famed for the quality
of his liquor, and so the term the real McCoy
comes from him, or it refers to him because his

(21:57):
liquor was supposed to be the real thing. He also
and always wonder if they had a romance. But another woman,
her name was Gertrude Lithgo. She was a woman who
had worked for a liquor company and she was in London,
and as soon as prohibition passed, she is transferred by
her company to the Bahamas because they very quickly realized
that the Bahamas is going to be a in a

(22:20):
prime spot to make money off of this ill considered law.
And she eventually, for example, goes and sees what it's
like to be on a rum runner with Bill McCoy
at one point. Eventually she gets into the game herself
and is eventually arrested and tried in the district court
in New Orleans. So she was known as the bootleg

(22:40):
Queen of the Bahamas. I love that. I love that
there is a female rum runner as well. That was like, hey,
I'm getting into this game. She worked for a legit
liquor company, and then as soon as it became illegal,
she was like, forget that, forget this, by the book's nonsense.
I'm gonna make killer money like doing this illegal stuff. Yeah.

(23:01):
In fact, William McCoy he considered himself an honest lawbreaker,
which means I'm breaking an unjust law. That that I
I feel like there's a reflection of that with a
lot of people with a lot of illegal drugs in
the US now, there are people who like passionately believe
that they're on the right side of history by fighting
against these drug laws. Definitely. Yeah, Okay, So I'm assuming

(23:28):
that rum running ended because prohibition ended, You would be
correct that was the main reason, But that wasn't the
only reason. Certainly, the most obvious is the end of prohibitions.
But that doesn't mean that rum running ends entirely, because
there are plenty of people who want to evade all
the tax laws around alcohol, and so there is still

(23:52):
certainly on some ongoing efforts to bring in liquor so
they aren't having to pay taxes on it. It was
a lot tougher to make a ton of money smuggling
in cases of liquor. If anybody can get it at
your local ABC store, that is a good point, because
liquor is one of the most highly taxed goods, right,
That's why people buy liquor at the airport tax free,

(24:13):
like the duty free shop. That's why that's a popular practice.
And you could also make more money smuggling in people.
The legacy today is that instead of rum running, we
have everything illegal you could possibly think of running. And
in the nineteen twenties that was the first time where

(24:35):
we began to see more widespread restrictive immigration laws, and
so it became much more difficult to immigrate to the
United States. And so what happens and increase in smuggling immigrants,
and guess what happens in the nineteen thirties. Marijuana is
now illegal. And there's another thing you could smuggle in

(24:56):
and flash forward to the nineteen seventies and the War
on drugs, which continues to this very day. There you go,
the legacy continues. Yeah, I'm sure modern day people who
smuggle in cocaine and marijuana and every other illicit drug,
the precursor of them were the run rum runners, the

(25:20):
illegal electronics that even that shouldn't be here, like getting
around tariffs or any kind of restriction at all that
the federal government puts on imports. Oh, that's interesting. So
if you buy an iPhone off of some dudes, like
the inside of some dudes like trench coat on the street,
have you done that before you're talking about this is

(25:41):
like a oh, yeah, there's a guy in my neighborhood
that does this. Oh there, there definitely is a guy
in my neighborhood who destin this. I have not personally
bought and I phone from him, but there definitely is
a guy in my neighborhood for sure. Yeah, we've learned
today that rum running was pretty impressive, how advanced they
were in terms of getting around the law. So listen up,
illegal smugglers of all kinds. Tip your cap to the

(26:05):
rum runners. Back in the day. Because they probably set
up a lot of like ways of doing business that
help your business. Still to this day, I almost feel
guilty because I feel like we're giving some advice to
future illegal occupations. Don't break the law, kids, don't break
the law we had jobsolete, do not condone law breaking. Hey, listeners,

(26:27):
what did you think of today's episode and what would
be the first thing you would drink the second prohibition ended?
Let us know on Twitter at job slete Pod. Also
follow us on Twitter, and it would be very helpful
if you could rate and review our podcast on Apple Podcast.
It really helps us out a lot. Thanks. Job Slete

(26:48):
is produced for I Heart Radio by Zealots Manufacturing hand
Forge Podcast for You. It's hosted by us Helen Hong
That's Me and Matt That's Me. The show was conceived
Eve been produced by Steve Za Markey, Anthony Savini, and
Jason Elliott. Our editor is Tommy Nichol, Our researcher is
Amelia Paulka, our production coordinator is Angie Hynes, and theme

(27:12):
music is by the mysterious Breakmaster Cylinder. A special thanks
to our I Heart Radio team, Katrina Norvelle, Nikki Etre
Ali cantor, Carrie Lieberman, Will Pearson, Connell Byrne and Bob Pittman.
Advertise With Us

Popular Podcasts

Las Culturistas with Matt Rogers and Bowen Yang

Las Culturistas with Matt Rogers and Bowen Yang

Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.