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July 7, 2025 47 mins

This week on Wicked Words we’re traveling back to 1923 Harlem and its seedy world of gambling and racketeering. Author Mary Kay McBrayer tells me about Stephanie St. Clair. She was one of the only female crime bosses in the city. Madame Queen was also a Black, self-made businesswoman. And a legend.   

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
This story contains adult content and language. Listener discretion is
advised by the way.

Speaker 2 (00:14):
Her business definitely was illegal. She definitely was a criminal,
but first she was a businesswoman.

Speaker 3 (00:26):
I'm Kate Winkler Dawson, a nonfiction author and journalism professor
in Austin, Texas. I'm also the co host of the
podcast Buried Bones on Exactly Right, and throughout my career,
research for my many audio and book projects has taken
me around the world. On Wicked Words, I sit down
with the people I've met along the way, amazing writers, journalists, filmmakers,

(00:48):
and podcasters who have investigated and reported on notorious.

Speaker 1 (00:53):
True crime cases.

Speaker 3 (00:54):
This is about the choices writers make, both good and bad,
and it's a deep dive into the unpublished details behind
their stories. This week on Wicked Words, we're traveling back
to nineteen twenty three Harlem and it's see the world
of gambling and racketeering. Author Mary Kay McBrayer tells me
about Stephanie Saint Clair. She was one of the only

(01:17):
female crime bosses in the city. Madame Queen was also
a black, self made business woman and a legend. Let's
just start with the kind of themes of this book.
When I talk to my editor about a book that
I might want to write, she always says, why does
the audience now in twenty twenty five care about this story?

(01:41):
What are the themes that resonate with this audience, this
current audience. What do you say about your readers and
why they think that Queene's story will be important?

Speaker 2 (01:50):
Sure? I mean, I think the best question to ask about,
you know, especially nonfiction, is like who cares like and why?
So I think that's like the most important question. But
I think I think this one touches on several different
big frame narratives that are not only happening now but
are kind of like almost Joseph Campbell level of classic.

(02:10):
One of them is, you know, this is an immigrant story.
As Americans, we all have one, well not all of us,
but a lot of us have one. And I think
also as Americans, we really love a gangster story. And
I think the reason we love it is because it
is an American dream success that was a success against

(02:31):
all odds, Like they not only did it, but they
did it outside of a law that was actively trying
to prevent them from doing it. So I think that's
one of the reasons and then the third one, of course,
is like this is an element of American history and
black history that you know, almost got lost. And I
think it's an important story because she was a West

(02:53):
Indian immigrant in the nineteen twenties and thirties when that's
that's when her business was taking off, and we don't
hear about that story very much. Also, like she held
her own against some of the really well known names
of gangsters in that period. So those are I think
some themes that made it stand out to me. And
I think if anyone is interested in any of those

(03:15):
big three things, I think that they would probably be
interested in this story.

Speaker 3 (03:19):
I think that the cases that fall in this category,
like the al Capone stories and stuff, are fairly well,
you know, treaded at this point.

Speaker 1 (03:29):
But I think that her story is unique. Now. I mean,
her official name is Stephanie Saint Clair.

Speaker 3 (03:35):
Do you call her Queenie or what do you I
just called her Queenie, But we can call her whatever
you want.

Speaker 2 (03:39):
We can call her whatever you want. I think she
used all of those names interchangeably, and I think she
had some added to the pot, Like some people called
her that tiger from Marseille. We had Madame Queen. We
had Madame Sinclair, Madame Stephanie Sinclair, Madam Stephanie, just Stephanie. Like,
there's a lot of different options we can use it,
I mean, depending on the content, right, go back and forth.

Speaker 3 (04:02):
Where do we start with her story? Do we start
in the West Indies where she's from, or wherever.

Speaker 1 (04:08):
You want to start. It's fine with me.

Speaker 2 (04:09):
Yeah, so I guess I probably should say this up top.
I did do so much research on this story, and
sometimes the facts that I needed just were not there.

Speaker 1 (04:18):
Welcome to historical true crime and nonfiction.

Speaker 3 (04:22):
It's awful sometimes, yeah, especially I imagine for doing research
on a black woman, you know, in the nineteen twenties.
I wonder if did you have immigration papers for her?

Speaker 2 (04:34):
Great question? Yes, and also they were sort of wrong.
She's a slippery person, right, like she wanted to be slippery.
She was intentionally evading having a lot of stuff on paper,
unless she was the one who put the pen to
the paper, in which case there's a lot to go on,
which is really fun. So do we have immigration papers? Yes,

(04:54):
sort of. She grew up in Guadeloupe and when she
was thirteen, we think her mother booked her a passage
to Montreal. Their first language was French, so it made
sense to go to Montreal. But she did go by
way of New York City, which I think is how
she kind of got the bug of you know, Harlem

(05:15):
is maybe a really great place to be. But yes,
so thirteen is what her birth certificate said, but the
ship manifest says twenty three. That's a big difference for
being that young. And it seems like this was an
endianjured servitude type of contract that got her to Montreal.
They did have like a big pipeline of West Indies

(05:37):
to Canada at the time. That was like technically no
one was allowed to immigrate from the West Indies unless
they were like a domestic servant because no one already
in Canada wanted to work for that low of wages.
So it was like, you know, a terrible story as
old as time. But I think that that's how she

(05:57):
got to Montreal and why she stopped in New York first.
But there was that discrepancy on the paperwork, So was
she thirteen or twenty three? Was the ledger Man just
you know, not a great clerk. Did he write it
down wrong? Did he misunderstand was it a language barrier
or was she actually just trying to come across as
twenty three because then people would take her seriously. Like,

(06:18):
I feel like it could be any of those, but
the most likely one is probably the last one. So
that's kind of like the first record that I was
able to access is like the sketchy one, or that
kind of brought her into Northern America.

Speaker 1 (06:31):
Did she make it to Montreal and then came to
New York.

Speaker 2 (06:34):
Yes, so she stopped through New York City, And I'm
thinking again, it makes sense that she would be at
a sort of sponsorship group house for you know, temporarily
while she got on her feet, like people who were
already making it in New York would help her along.
And I think that was also a requirement for immigration
at the time. But she stopped there and then went

(06:55):
to Montreal, where she served a two year contract as
a domestic worker, and then when her contract was up,
she was like okay, bye, and then came right back
to New York. So she worked in a home. But
it also seems like she picked up some really important
skills at that time, like dressmaking. She was a really
proficient dressmaker, and also because of her later line of work,

(07:18):
and because there's a lot of math in creating address
from nothing, she was really math brained, which was challenging
for me to write as a person who is not
math brained. So same, Yeah, it was fun, but it
was definitely a challenge.

Speaker 3 (07:33):
So tell me about Harlem when she really I know
you said her business is starting to take off in
the nineteen twenties, but when she comes to New York,
it's in the nineteen tens.

Speaker 1 (07:43):
Is that right?

Speaker 2 (07:44):
Yes, so I can't remember the exact year off the
top of my head, but yes, she came through New York,
went to Montreal, came back to New York, and then
there were several years where she just was kind of
lay and low till about I believe nineteen twenty three,
which is when she just all of a sudden had
the best numbers bank in the city, which is a

(08:07):
huge deal because there were many players. They were all
West Indian and all of them were men except for her.
And just a little bit of background about like the
numbers racket, because I didn't really understand what that was.
It's almost horse betting, it's almost betting on horses, but
it was basically the lottery like today. I don't know
if this is maybe like a little bit of a spoiler,
but it is the New York State lottery now. At

(08:30):
the time, though, everyone and everyone pretty much every day
would put a penny on a three digit number, and
you know, some people bet the same number every time.
Some people had like dream books that they would decide
what they were going to bet on, and it came
from the last digits of the horse races. At that time.
It seems very much like a game of chance at

(08:52):
first glance. But when you know the law of large
numbers and you can do that kind of math in
your head, I can't, but she could, you can get
really strategic about it. So my theory is, and it's
supported by later evidence, if not directly. My theory is
that she got really good at playing the numbers and
she won at all of the major banks at the
same time. And that's relevant because this was an illegal business,

(09:15):
right like nobody is keeping their money in an actual bank,
which is actually you know, probably good for them because
of all the bank runs that happened later in that decade,
like it would have been kind of gone. But because
again they're all West Indian, right like they're banking offshore,
so when someone hit the numbers big for a bank,
they'd pay out, but they had to go wire it back,

(09:37):
so the banks would kind of shut her for a
couple of days until they could get you know, their
feedback under them. My guess is that she did that too,
like all of them at the same time, because she could.
She could do that, like her brain just worked like that.
So while they were down, right, like all of their runners,
which are the guys who actually took the numbers and
took the money back to the bank, the you know,
the illegal bank, they were all out of work right well,

(09:57):
while the banks were shut. It's just a few days.
But like if you can pick ups, I'd work with
this other woman whose bank just suddenly popped up, do it.
So she kind of poached all their guys while they
were down, and then she's like one of the big
players in the game.

Speaker 3 (10:13):
So let's go back to you said, there's kind of
like a big jump. How does Queenie go from being
a domestic worker, you know, in Montreal then she comes
back to New York. How does she do that and
then go to something that is you said, this is illegal.

Speaker 2 (10:28):
Right, Yes, so everything's illegal during prohibition by the way,
like all the stuff that people want to do for
fun is like illegal, which makes it dangerous. Like now
you know our alcohol is regulated and more fun and yeah,
more fun because nobody's watching, right, It also made it
more dangerous because nobody's regulating how much alcohol is in
your alcohol. No one's regulating like if it's going to

(10:48):
give you jake leg no one's regulating how you're getting
the alcohol. You know, it's horrible exploitation. It's a lot
of stuff going on that is better I think regulated
because people are going to do it, so you should
be able to be done safely. Yeah. So I think
you asked about there was a gap of how she

(11:09):
went from domestic work to running this illegal game.

Speaker 3 (11:12):
And I mean morally, I mean, how do you go
from I mean, we don't see any bad background from
her beforehand, right, Yeah.

Speaker 2 (11:20):
We have records of her getting married in a Roman
Catholic church, which like they don't just marry people like
you gotta show and prove that you mean business if
you're getting married in a Roman Catholic church. It was
also like a few days after her eighteenth birthday, so
it seems to me like somewhat of a convenience. Again,
maybe not, but we don't know about him any at
all later in her life. So and they never got

(11:42):
formally divorced, So there's that also, like you do have
to be an honest person right to work in someone's
home period. You can't be a thief, like they would
know immediately and you would get fired and then no
one would give you a reference and that would be
the end of that career. So we know that she
was at least a good person to work for you
that there's no ay on that. And we know that
she was a hard worker because it's hard to make

(12:03):
money in those fields now then very very challenging, so
somehow she knew how to manage her money like she
was doing it. I also think that because it wasn't
really a game of chance, it wasn't really gambling, like
if you think gambling is bad, like is a sin potentially,
but this is not really gambling. It's strategy. Then it's like,

(12:25):
you know, with one eye closed, I can get there,
you know, like I don't see anything wrong with that.
And then I think another important thing to remember about
her in contrast to all of her contemporaries is that
she was a business woman first, Like she was running
a business and her business happened to be illegal, and
she got away with doing it with just you know,

(12:45):
paying a few bee cops for a long time just
to like look the other way, because no one was
getting hurt. Like she wasn't stealing anything. Like people were
having fun putting a penny, literally a penny on a
number and then sometimes it paid out, and then they
had a party and spread it back around among everybody.
So when I think of someone running in a legal
gambling racket, she's not the one, you know that pops

(13:07):
into my head as a racketeer.

Speaker 3 (13:09):
You know, people must have thought it was odd that
it's this black woman who's running all of this, which
I know you say in the book was incredibly unusual,
unheard of really in this time.

Speaker 2 (13:18):
Yeah, And I think part of the gap that we
were talking about, not necessarily morally, but just like what
made her qualified to do this is that a lot
of people say that she worked for another bank first,
so that she had some name recognition and she kind
of learned like how the books ran and that kind
of thing. And although it's not written down because they

(13:40):
didn't write anything down. Really, all of the evidence leads
to that she worked for Casper Holstein, who was also
like a pretty good guy, Like he was a huge philanthropist.
He donated like towards girls dormitories. I think in the
British indies, he's the guy you want to make a
lot of money because he gives it back, if that
makes sense, Like he knows how to help the community

(14:03):
and he would put people on like he was almost
an angel investor and a lot of companies, And you
can see the similarities in her work once she kind
of made it, she was doing that as well. Another
reason why I think it's him is because his bank
didn't shut down, Like she didn't box him out, hmmm
when she boxed everyone else out. Yeah, So that's why
I say, like, no, it's not written down, but the
evidence points to that this is the most likely case.

(14:25):
Plus to your credit, like who would who would bet
with her if she had no cred Yeah? Right, Like
who would do that? Even a penny? Like it's you know,
still money, right, So I think that's how do you.

Speaker 3 (14:36):
Have any idea what her profit margins were? I mean,
was this thousands and thousands of dollars.

Speaker 2 (14:40):
I wish that I did, but I do think that
it was small enough potatoes where she could fly under
the radar. Got it both with the actual government, you know,
like legal people who it was also Tammany Hall at
the time, so like they're gangsters too.

Speaker 1 (14:55):
Yeah, everybody's everybody's corrupt.

Speaker 2 (14:57):
Right, So it was it was small enough that she
could hide it because she wasn't, you know, going around
dressed in like a zoot suit. I mean, she was
like classy, Like her photos are amazing, like height of glamour.
And she was a dressmaker too, so you know, everything
is just too a tea like tailored to her, which
I love when I can find photos of her because

(15:18):
it's truly amazing, Like how is that a metallic dress?
You don't even have synthetic fabrics?

Speaker 3 (15:22):
Hardly tell me about her family back home? Does she
remain in contact with them in the West Indies? Does
anybody come over at all to be with her?

Speaker 2 (15:30):
Don't. I don't think that she really had any contact
with her family at home that I know of. She
could have, it seems like she would have, but I don't.
I don't know for sure. She also, as far as
I know, after she got married. They didn't really have
a relationship very long at all, but they never got divorced,
which makes me think that, you know, she might have

(15:51):
been helping him out. There's also some discrepancy about whether
they had a child together. There is a birth certificate,
but that's kind of it and it doesn't it's not
really conclusive to say one way or the other. But
I think that if she had had a child, she
would have been at least supporting him financially, so because
that's the kind of person she was. So she might
not have been supporting her actual family, but her community

(16:12):
was very important to her, and maybe that's a reason
why is that she didn't have much contact with her
biological family.

Speaker 3 (16:21):
So this bank system seems to me to be fairly easy, right.
They initially put the money in and then if they
hit the numbers, she does the payout. But is there
any circumstance where she felt as far as you know,
where she would have felt or she says she felt intimidated,
you know, did she talk to the wrong cop or
you know, I think I think we're going to get

(16:43):
into some turf, you know, wars. I don't know if
WARS the right thing, but you know, turf wars between
her and other organized crime members, so you know, kind
of tell me when things ramp up a little bit
for her.

Speaker 1 (16:55):
You said she's small potatoes. Right now, I think.

Speaker 2 (16:57):
She came across as being pretty small potatoes because she
was good at being discreet. But yeah, so to your point,
it didn't say stay a secret very long. That she
was kind of killing it, as you probably know, and
as we said, you know, gangsters don't keep their money
in real banks, so where was it. I think she

(17:18):
probably also had a dressmaking front, which was actually also
a legitimate business, so probably it was laundered in that
way as well. Once she got into business, it was
kind of tough going because she was a lady, and
she was a woman, and she was black, and you know,
all of those things kind of set her at a disadvantage,

(17:40):
if you will. In the early nineteen twenties. The first
sort of difficulty, I'll say it that way, is that
the regular police got wind of her and they demanded
that she start icing them, and then she did, and
of course they didn't protect her from anything, like they're
the bad guys too, So she paid for nothing, right,
did she just basically extortion. And then she got busted

(18:03):
anyway because the police planted policy slips on her twice.
Policy slips are basically the receipts of the bets, and
they were so silly about it, Like the way they
did it. They broke into her apartment at four h
nine Edgecomb, which is like the place to be in
sugar Hill, and they tossed her apartment and they broke

(18:25):
her the handle on her wardrobe, and the guy who
smashed the window open like cut his hand, and then
there's like blood everywhere, and it's on this box where
she kept her cash, and the cash is gone, and
they in the hall closet, which shout out that she
had a closet and night in the nineteen twenties in
New York City, they stashed her some fake receipts basically

(18:49):
in that closet, and then the other cops came in
the front way and were like, we found them because
they had just planted them, like just then. Her defense
was basically like I was at my bank, why would
I take receipts home? Like why would I do that?
If I was doing what you say that I was doing,
That doesn't make any sense that I would bring them

(19:10):
from work to home, like, it doesn't make sense. So
she did get busted for that. They didn't like that defense.
She went to prison or women's prison I think is
what they called it, which sounds pretty rough as far
as work.

Speaker 3 (19:25):
Okay, so my question going back is, well, first, now
I understand what ice means icing, so you know, paying
off the police, right, yes, why would the police want
to You know, if they've got the golden goose, this
woman who makes a lot of money, who is paying
them off, why would the police want to stop that

(19:46):
by busting her to begin with? I mean, what is
their motivation there? You would think they'd want to keep
this going forever.

Speaker 2 (19:52):
I would think. So that's exactly what I would think,
And that's a great question. The thing that I have
deduced is that they were all so taking payoffs from
her competitors. So who's paying them more would probably be
some of it, especially when and this is a little
bit later, but eventually, right alcohol becomes legal again, which

(20:14):
leaves a whole bunch of thugs out of work. So
they kind of wised up that she was actually making
a very good business, like not extravagant because that's not sustainable,
as they should have learned to come too hard out
the gate. But eventually that did end up escalating into
a turf For the first time she got put into jail,

(20:36):
she kind of realized she kind of like wised up,
like I'm not going to be able to do this
myself and keep my hands clean. So you know, she
has a pulse on all of Harlem. This is when
she heard about Bumpy Johnson. She recruited him like two
days after getting getting discharged from jail, So she heard
about him while she was in prison because he was

(20:58):
actually ultimately her successor of her business, which is kind
of cool. But he at the time was a bodyguard
for another banker, Alex Pompeii's. He was Bumpy Johnson was
fifteen years old, and she learned that a mugger was
trying to come at his boss and he cut his
throat and gutted him on the street. Yeah, and she
was like, yes, that that's what that's why I need

(21:21):
the fifteen year old savage.

Speaker 1 (21:23):
She needs a bodyguard, that's what she's figuring out.

Speaker 2 (21:25):
Yeah, So she hired him as a heavy basically, so
like if any one was given her a hard time,
she'd call the muscle and that was him. By the way,
like her business definitely was illegal, she definitely was a criminal,
but first she was a business woman and she just
didn't have the protection from the government, so she had
to hire people to keep her safe. And you know,

(21:45):
if you're hiring somebody for your physical protection, the meaner
the better, especially because she prided herself on being a
lady who you know, didn't engage with that kind of behavior,
I guess. Anyway, by the time she got out of jail,
alcohol was legal again. Like we said before, it's so
it was just a matter of time before those gangsters
who were now out of work realized that her business
was really profitable and the syndicate was coming for her.

(22:09):
That's like the basically the Five Families plus Dutch Schultz.
So the five families were like the Italian heads of
all the different branches of the mafia, and Dutch Schultz
was in there too. He's kind of grandfathered in. He
was not Italian and he was not Catholic. He was
the only I think he was German and Jewish, so
he was definitely the outlier by a lot, and he

(22:31):
knew it and he was. He was just kind of
a jerk, like they all are jerks, you know, they're gangsters,
but he especially was like very loud mouthed, shot from
the hip, like a real liability. That makes sense when
you're running an illegal business. He was actually the one
who was responsible for vandalizing all the local stores who
didn't pay his guys for protection in Harlem. Yeah, Stephanie

(22:52):
Sinclair told reporters in one of the articles that actually
she didn't write. One of the Amsterdam News reporters interview
her and wrote this, so it's a little bit more
I think trustable, because it was not something that Stephanie
Sinclair paid the paper to produce as an advertisement, which
she did, okay, like she was the Queen of pr
like she was. She had like these thirst trap selfies

(23:15):
from like the waist up. It wasn't a selfie obviously,
but that's what kind of looked like. She'd have like
a turban and like big jeweled ear rings and fur
its just like yeah, I'm gonna read this article for sure. Anyway,
this one was not that. This one was like a
Marvel Cook who was like an up and coming reporter
at the time, interviewed her, and she said that Dutch

(23:36):
Schultz sent one of his guys to her apartment to
beat her up and intimidate her into forfeiting her business.
I mean he did do that, but she shoved that
guy in that closet, the closet, I'm telling you closet,
and then she called her guys to come take care
of him. So like no one could find Max Rennie,
which was the guy who came to her apartment and
tried to intimidate her, Like he's just disappeared.

Speaker 3 (23:58):
So when she gets out of prison after this time period,
she just goes right back to the banking scheme stuff.

Speaker 1 (24:05):
Does she expand at all or no?

Speaker 2 (24:07):
I think she's expanding the whole time. I don't think
she like the bank never went under, like she just
had such a good idea of how the numbers and
people worked that like by all the accounts I could find,
Like her business didn't stop just because she went to prison,
Like it just kept going because people were still getting paid.

(24:27):
She had people who were good at their jobs. And
I think she kind of knew in a business like this,
you're gonna go to jail, Like that's definitely going to
be part of your life. So I think she had
prepared for it because she did come out and then
she just went right back to work. She like hired
her bodyguard force. I wish that we had more records

(24:48):
about what her profit margins were, like, what was she
pulling in in a normal day. I know that she
started her company with I think twenty thousand dollars, which
today is a ton to me, Like that's so much
to me.

Speaker 3 (25:00):
Let's see, let me find the numbers. Hold on, so
twenty thousand and what twenty three, nineteen twenty three, Yes,
that's when she came up.

Speaker 1 (25:07):
So that's about three hundred and seventy thousand dollars.

Speaker 2 (25:11):
That's amazing.

Speaker 1 (25:12):
I'm so proud of her.

Speaker 3 (25:14):
So she comes out, she does this, she gets you know,
her bodyguards together, and now you said the syndicate is
coming after her and Dutch Schultz is coming after her
to intimidate her. I think now is a good time
to talk about her personality because you know, I mean,
I don't think you have any illusions that she is
some perfect woman. In this book, it sounded like she

(25:35):
could be pretty acerbic and rowdy, and you know, she
had a foul mouth and all kinds of stuff. Will
you kind of give us some insight into her character
and what objective people around her kind of thought of her?

Speaker 2 (25:47):
In general, I think that she was probably pretty scary.
I think she was probably very quiet, which you never
know what quiet people are thinking, so that's a little unnerving.
She did speak multiple languages, which is amazing to me
as well. I don't think she ever lost her accent,
but I don't know what that accent really was. I

(26:07):
think it was probably like a you know, a mash
up because she was West Indian and then she lived
in Montreal, which is very different, and then you know,
and then New York. We do have some direct quotes
from her both, not only in the things that she
wrote herself, of course, but Marvel Cook has her on
record as saying like she's gonna crimp nut sholts like hair,
Like she's gonna put like a wave in him, Like

(26:28):
was she gonna break him? Like what does that mean?
You know? Like that kind of slang is so fun
to me. It would have been terrifying in person, Like
I think she was just like probably the best dressed
person in every room, but like in a very demure way,
like a subdued type of way where she knew what
she was doing, like she didn't have to be super flashy.
She did have a really filthy mouth, which, of course
you know she's a gangster. I mean she's a lady too,

(26:50):
but we can all get there, right, Yeah, I guess
you have to talk like that to make people take
you seriously in that line of work at least. So
there's that. And then also one thing that is very
like character defining to me is that, like I said before,
Schultz was a real loud mouth and a liability for
the syndicate. So when he threatened to assassinate the district attorney,

(27:10):
which was Thomas Dewey, the other gangsters he worked with
did not like having that attention, so his own guys
put a hit on him, like his own guys in
the Sive Families are the ones who assassinated him and
a bunch of his people. But I think from what
I remember reading, Stephanie Sinclair is the one who told

(27:30):
Thomas Dewey that Dutch Schultz said that. So we're getting
your information third hand. If I know, Madam Queen, he
may or may not have said that. But you know,
she's playing chess the best way I think to get
out of a sticky situation when you don't have the
manpower is to have your enemies annihilate themselves. Yeah, to
fudt them against each other. Schultz survived the assassination attack.

(27:52):
He was in hospital, Like okay, also, and how bad
of a shape do you have to be to go
to a hospital when you're a known gangster. He's about
to die, but he survived that, and then he got
blood poisoning, and so then he started talking out of
his head and there are long transcripts of what he
was saying because everyone knew he was a criminal. But

(28:12):
in order to pin a criminal down, you have to
do it legally, which is really that's the hard part, right.
So they had a clerk in his hospital room typing
everything he said, which is fascinating to me because it
was just nonsense, like crazy stuff.

Speaker 1 (28:28):
Did you talk about Stephanie Sinclair?

Speaker 2 (28:30):
No, he didn't say anything important. He didn't say anything
relevant at all. He was talking about playing jacks and
like something's on the roof, like nothing relevant. They totally
wasted that resource. But on the off chance that he
was going to confess to something, they needed someone there.
But she while he was on his deathbed, talking out
of his head, dying of blood poisoning. Stephanie Sinclair sent

(28:51):
him a telegram that said, as you sow, so shall
you reap? And she assigned it Madame Queen of Policy.
That's really twisting then, I I think in a very
fashionable way.

Speaker 3 (29:02):
She mentions in this article that you know she was
going to crimp him, which yes, we know is not
a hair. Why would she agree to do an article
with this woman, Marvel Cook? I mean, I'm confused about that.
What kind of criminal does like a feature article on themselves?

Speaker 2 (29:19):
Yeah, she's so twisty. It's so interesting to me that
she was never hiding the fact that she was running
this business from what Again, from what I remember from
the records that I can recall at the top of
my head, she kept really detailed books, including like the
badge numbers of the police she was paying off on
a regular basis, and all the money that she was
taking in, and all of the taxes she was paying

(29:42):
on the money that she was taking in. So I
think that she was somewhat secure behind that. I think
that there's also a way of like doing a not
exactly a bait and switch. But if you go to
the police and say, hey, I was doing this thing,
but this other thing happened that was really important, They're
going to focus on the bigger thing, Like he wasn't

(30:03):
a vice cop, you know, like he was trying to
bring down organized crime. And she's over here saying, like
this guy specifically I him. He said, he's trying to
kill you. Like that's enough, you know. So I think
that there that she could have not hide but kind
of just smoke and mirrors with those two things as well.

Speaker 3 (30:21):
Do you think that she came close to being I mean,
I know that you know, there's this guy coming out
to intimidate her and stuff, but is there anyone else
who's targeting her seriously other than Dutch Schultz. I know
that you've got Bumpy Johnson around trying to protect her
and everything, But did she feel like she was in
major danger at some point?

Speaker 2 (30:40):
He was the main threat because he was the one
who didn't have any other thing going except for his
beer business. The other gangsters, you know, they were already
into drugs, They were already into dealing drugs they had
and they were running gambling rings as well, so they
had other revenue. Streams if you will, besides just alcohol,
and they were not out of work completely. They you know,

(31:01):
they lost a vertical right, but that's okay. You can
stand on the others if you need to. He had
already boxed out all of the other bankers by the
time that he went to her because he was busting
their plate glass windows and like, yeah, your insurance might
pay for that, but you're going to be out of
business until you can get it fixed. So there's that, right,

(31:23):
Like he was intimidating people and you know, having them
lose money so that they kind of had. They were
kind of it was kind of forced right to kind
of work with him, and I can't remember off, I
can't remember. I'm sorry, but he also you know, snatched
the other businesses from the other West Indian bankers.

Speaker 3 (31:38):
Did she ever expand past the racketeering part the banking
or was that primarily what her business was when she
was active in Harlem?

Speaker 2 (31:46):
That was primarily her business as I understand it, and
I think she also had a dressmaking store, But I
don't think she ever went into anything harder than that. Okay,
Bumpy Johnson did for sure afterward, but I don't think
she did.

Speaker 3 (32:00):
So, what was her involvement with Lucky Luciano? Is this
somebody that she ever you know, he's a well known gangster.
Was this somebody that she ever met in person and
had discussions with?

Speaker 2 (32:10):
From what I can tell, the remaining five families just
kind of left her alone because again, they had other
things going on. Lucky Luciano as actually famous for being
the first gangster that didn't go down for tax evasion,
Like they brought him down, but it wasn't because someone snitched,
and it wasn't because he evaded his taxes. He actually
went to prison for a prostitution racket. Thomas Dewey actually

(32:32):
put together the one that Dutch Schultz threatened his life.
He put together a task force trying to destroy organized crime.
And all these tips kept coming in from sex workers
or people who live next to the brothels who were like, hey,
I don't know how this is happening. Every time they
get busted, they're like back in business in twenty four hours.
And then they noticed like, oh they all have the

(32:54):
same bondsman, Okay, there is one guy running all of this.
And so that was Luciano who and I think he
came into power right after Schultz, but there was another
assassination first and then he came in. I don't think
she ever interacted with him, like head to head, but
they were working simultaneously.

Speaker 3 (33:12):
Did these people, these other the syndicate, did they consider
Harlem to be part of their territory.

Speaker 1 (33:19):
I would not have thought that.

Speaker 2 (33:21):
I think so again, because they had different means of income,
Like they weren't exactly in the same business. So there
were definitely speakeasys and nightclubs in Harlem, like those were
some of the everyone's favorites, like we have the Cotton
Club and the Savoy up there right. You know, they're
the ones getting the booze to those clubs, I'm sure.

(33:41):
And Stephanie Sinclair wasn't doing that, Like she wasn't even
probably partying there. She probably knew everyone, but she didn't rage.
I don't think. Yeah. So I think that they weren't
exactly competitors until Schultz was like, I'm taking your.

Speaker 3 (33:53):
Business at the end of prohibition. Did she see her
business dip at all or no?

Speaker 2 (34:00):
It seems like it was consistent.

Speaker 3 (34:01):
Tell me a little bit more about her relationship with Bumpy.
I mean, how long does this last with him being
a part of her bodyguard, the head of her entourage
of bodyguards. Is this a long term position for him?

Speaker 2 (34:15):
As far as I know, it lasted until they both died,
like their friendship was lifelong. And I say that because
Bumpy Johnson's wife, Mami, wrote her memoirs later in life,
so I never got to talk to her, which is
no crushing, But she has a really great memoir, The
Rap on My Husband, and she wrote that they were
lifelong friends, like she put him onto the business. And

(34:38):
then whenever she and I don't want to give too
much away, but whenever she went to prison for the
Long One, which actually was not for racketeering, so that's
fun little twist at the end. Whenever she did go
to prison for the big one, he is the one
who kept her business running inherited it and Mamie says
that he is the one who kept her up for

(34:58):
the rest of her life. Hmmm, that makes sense. Maybe
she was working for him, maybe they worked together. Maybe
she was like, no, I'm out. We don't know. I
can't imagine her saying like no, I'm out though, mm hmm. Yeah,
they were lifelong friends. I think they died within a
few weeks of each other. I don't think that their
relationship was romantic at all, but I think that they
were very close coworkers and friends.

Speaker 3 (35:20):
So there is a switch at some point where Stephanie
Saint Clair kind of has to pull back on her
illegal business. And you know, am I right in remembering that,
she turns the reins over to Bumpy Johnson more and
he's the one that's sort of the one dealing with
all of these folks.

Speaker 2 (35:39):
Yeah, so she actually went to I believe she served
two shorter sentences for numbers again. The second time. It
was also a plant, like she was doing it, but
they planted the evidence on her, actually on her person.
They like shove it under her arm and then like
I saw her. I mean she had it as soon
as I came up. So she did go to jail
for that. And I think after she was released for

(36:01):
that one is when they was when she was like,
you run this side of it. I'm going to focus
on like the philanthropies now, which is kind of what
you want to do. You know, when you're building a business,
it's like someone else handles the day to day and
I focus on expanding the business or giving back to
the people who have supported me all of these years
and that kind of thing. So it seems like she
shifted to investing in local businesses after that second time,

(36:24):
after it kind of calmed down, and she, I guess
knew the ropes well enough or he had been trained
well enough to just take over, because she would take
meetings all the time for local startup businesses who needed
the funding just to get started, which I think is
really cool that she went in that direction.

Speaker 3 (36:41):
She then transitions, you know, away from that business into
more like political reform. So tell me a little bit
more about that. I mean, she has gone from kind
of underworld boss in a way to like a legitimate
political reform or activist.

Speaker 2 (36:58):
Which is another kind of cool, like gangster turned civil
rights activists. Like that's amazing, yes, And I think one
of the reasons why she did that is because it
affected her directly too, because she had been I guess
victimized by the police. Right, they're all corrupt, and she's like,
we have to elect some new officials, Like, everybody, go
vote for this guy who wants to clean up all

(37:19):
of this terrible organized crime, like he wants to get.

Speaker 1 (37:22):
Rid of it.

Speaker 2 (37:23):
Go vote for him, and she would also ask her
people to vote for people who did what they said
they were going to do. And these are again in
the advertisements that she paid to have published in the
Amsterdam News. They weren't really advertisements though, they were like
open letters. For example, she wrote some that were detailing
the rights that you have when a police person comes

(37:45):
to your door and says he's going to search your apartment.
Right like, she's like, they can't come in without a warrant.
You can ask for the warrant, and this is how
you do it. Like she was telling people, you don't
have to let police in, even if they say you
have to let us in, you don't, like, it's the
law that you don't. And I think that's really cool.
And I actually think that she probably learned that because

(38:06):
it happened to her, and because she told her lawyer
this should be illegal, and he probably said it is,
like it is illegal search and s sure, that's exactly
what it is. So then she would go, you know,
find those things that I'm thinking the New York Public Library,
who was amazing to me and I'm very grateful for
all of their records. And then she would you know,

(38:27):
almost verbatim put in, this is the law, this is
what you have to abide by and what you don't.
So search and seizure was one of them. Stopping on
the street was one of them. Yeah, I thought that
was a real example of using your status to help
people who need it.

Speaker 3 (38:43):
Was she less targeted at that point by the police.
I guess once they realized that she's no longer in
the numbers business and that Bumpy is the one running everything,
do they essentially leave her alone.

Speaker 2 (38:55):
I'm not sure, because I think a lot of the
elected officials were being replaced at that time because it
was happening at the same time where LaGuardia, I believe,
is the one who eventually said we're done and he
put real, real systems in place to affect change from
these particular organized crime syndicates. So that shift was happening

(39:19):
at that time, particularly after the Harlem riot where they
arrested a little boy he was like fifteen for stealing
a pocket knife and he went missing. He was fine,
but no one knew that and no one liked that
the police would not answer any questions, so there was
a riot on his behalf. Almost positive it was LaGuardia,

(39:39):
who was like, we have to get to the bottom
of this, like why did this happen? And he put
in a task force that basically like hey, everyone stay
calmed for a second while we figure out what happened
and what to do about it. And of course, you
know that didn't really work because people were angry and
rightfully so. They thought a little boy had been killed. Yeah,
and they like the papers were running pictures of him
with the policemen. They were like, that's for last week

(40:00):
when he got busted last week, and it was like
it was a police it was a picture from before
he was on probation. But still, I think, you know,
so much was happening at a time that like it
was kind of everything was a shuffle, like the teams
were being redistributed.

Speaker 1 (40:15):
I think her.

Speaker 3 (40:16):
Life shifts pretty dramatically when she meets who would be
her future husband, and you know, he has quite a
colorful background, I think, and you know, tell me a
little bit about that relationship.

Speaker 1 (40:28):
That's in the nineteen thirties after she's retired.

Speaker 2 (40:31):
Yeah, I hate him, Sophie abdulhamide.

Speaker 3 (40:34):
Well, they called him a black hitler, which is a
terrible Moniker, So there you go.

Speaker 2 (40:39):
So he helped head several This was not I mean,
this was long before the actual civil rights movements, but
they were civil rights protests. He's a big he's a
big part of the movement of don't buy where you
can't work, which good. But he also talked about, quote
getting the Jews out of Harlem, and I think he
meant did I'm not defend this at all, because that's unacceptable,

(41:02):
but I think he meant getting Dutch Schultz and his
cronies out of Harlem. That's not what he said. Calling
Dutch Schultz by name would probably be a death sentence.
So again, terrible, and the New York papers called him
black Hitler because of it. So I don't want to
tell too much of their love story because it's really
frustrating because he's the worst. That was the hardest part

(41:22):
of the book to write, is like why and only
what did this happen? But I think he was a
very skilled speaker, and I think he was very charismatic.
Case in point, he did lead a cult a little
bit later on, So he was terrible in her life
did change a lot, because when your partner is a
terrible person, it's very distracting from everything good or everything

(41:46):
at all that you're trying to do. So he definitely
used her. And I don't know how much of their
love was real. I think it had to have been
at some point, but ultimately devastation.

Speaker 3 (42:00):
Well, I was wondering about that, what their relationship was like,
and it doesn't sound like it was very good.

Speaker 1 (42:05):
Kind of from the beginning.

Speaker 2 (42:07):
It doesn't sound like it was very good. Well, they
met because he was asking her. It was one of
her business meetings. He wanted money for a startup for
humous business. I think was the first one, and she said,
you know, thank you, but no, like your business plan
is not it's not where it needs to be. And
then he came back the next day and she's like,
there's no way, there's no way you revised it. Since

(42:27):
then he's like, no, I just came here to hang out.
She's like, I don't have time for this. So he
came back again. He was like writing letters to her,
which everyone wrote letters to her, like that doesn't make
him special to me, Like she's amazing. Everyone's sending fan mail.
But he kept showing up and asking to talk to her,
and that's really flattering, you know, like that can get

(42:49):
you a long way, just asking questions about someone's life
and their successes. Like it escalated from there. I think
he was a good bit younger, not a not a
good bit. I mean, depending on which of those ages,
right you trust is about five years younger. But that's
how it started, is he wanted money from her, and
then he ultimately ended up. They got married, but it

(43:10):
wasn't a legal marriage. She never divorced her first husband.
No one ever said this, but I think that was
her doing. I think it was on purpose that they
didn't get legally married, because what they break up, he
gets nothing. Right. Yeah, oh, it doesn't seem like it
would hold up, not when she was already married.

Speaker 3 (43:25):
Right, What is her legitimate business at this point is
at the dressmaking shop?

Speaker 1 (43:29):
Is that what she's doing?

Speaker 2 (43:31):
I'm not sure, I think so.

Speaker 3 (43:32):
We don't want to give away too much about the ending.
It does not end well her marriage to him, but
eventually she ends up on her own and seems to
live a fairly long life after that. But it doesn't
sound like she socialized. She certainly was not at the
height where she was before, but it does sound like

(43:54):
she had a kind of a good conclusion on her own.

Speaker 2 (43:58):
I think so. I think what you said earlier about
it didn't end well is absolutely correct, but it did
end spectacularly. You were also right in saying that ultimately
it does seem like she lived a long life. We
don't know the details of her middle age or late age.
She pops up here and there in an interview. Sometimes

(44:18):
she is not doing so well. Sometimes she has just
bought an apartment complex. Sometimes she has run barefoot in
front of a car to stop it. But none of
that really, Like she kind of disappeared herself, right, which
if you're a slippery person and you've been lying by
your age since you were thirteen, I think she's probably

(44:39):
picked up a few tricks where she probably did live
very well until the very end. That's the version that
I like to hear, Like I want to agree with
maybe Johnson, and that she lived very comfortably up until
the end of her life.

Speaker 3 (44:53):
So, what was the lesson that you learned from this book?
What was the big thing that you think, audience is
what your readers we'll take away from this.

Speaker 2 (45:01):
So aside from just learning that she existed and thrived
in a world created to keep her down. Madame Queen
was a really strategic person, and that's how she got
around those systems or got through them. I should say.
She didn't have the muscle of all the other gangs,
but she knew how to play them against each other.

(45:21):
She ran her business from behind bars. It seems like
she knew that sometimes in order to have a friend,
you have to be a friend. And unlike the other
mobsters of the day, she was a business person first,
and like I said, her business just happened to be illegal.
So she carved out a space for herself. She saw
an opportunity, as they say in The Great Gatsby, and

(45:42):
I think that that is very inspiring, even against like
all of the odds that she that she endured.

Speaker 3 (45:59):
If you love historical true crime stories, check out the
audio versions of my books The Ghost Club, All That
Is Wicked and American Sherlock, and don't forget There are
twelve seasons of my historical true crime podcast, Tenfold More
Wicked right here in this podcast feed, scroll back and
give them a listen if you haven't already. This has
been an exactly right production. Our senior producer is Alexis

(46:22):
a Morosi. Our Associate producer is Christina Chamberlain. This episode
was mixed by John Bradley. Curtis Heath is our composer.
Artwork by Nick Toga. Executive produced by Georgia Hardstark, Karen
Kilgarriff and Danielle Kramer. Listen to Wicked Words on the
iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

(46:44):
Follow Wicked Words on Instagram at tenfold More Wicked, and
on Facebook at Wicked Words Pod.
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Host

Kate Winkler Dawson

Kate Winkler Dawson

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