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June 19, 2025 • 35 mins

With Simon on vacation in jolly old England, Action Network host Chad Millman is joined by producer Matt Mitchell for another episode highlights great characters and moments in the wild history of gambling. Today Chad tells a story about criminal enterprises in Lexington, and Matt shares the story of the first American gambling syndicate, and a man called "history's most notorious big money gambler." #Volume

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Speaker 1 (00:08):
Welcome to the Favorites, the podcast part of the Volume
Podcast Network. I'm Chad Millman of the Action Network Today
a little bit of a different show. Simon, as everybody
knows from the last episode, is visiting with his family
in jolly old England. So I am joined because I
can't do this solo. I'm no Colin cowhard, I'm no

(00:31):
boss of the Volume Podcast Network. I can't go for
three hours mapping out my shows. Like it's a tree
with a lot of different branches, there's only one Colin Cowherd.
I need help. So joined by producer Matt Mitchell for
the fourth installment in our series of Great Stories from

(00:55):
Gambling's Wild History. As you guys know, I've mentioned this
a few times. I'm working on this book, so I've
been traveling NonStop. I've been digging into archives. I got
a couple of great stories that I'm going to share
of things that I've learned, really really cool stories, and
Matt is going to share some stories as well. Matt

(01:15):
doesn't even know what I'm going to talk about. So Matt, hi, buddy,
are you excited?

Speaker 2 (01:19):
I couldn't be more excited. Chad.

Speaker 1 (01:21):
All right, So this is direct from my book I'm
I'm giving a little bit away.

Speaker 2 (01:28):
Chad Milman wrote a book.

Speaker 1 (01:30):
It's such a good story every time I tell it,
and Matt, I haven't even told you this. People like
freak out. One of the guys who was known as
the bookmaker for the mafia, This guy named Ed Kurd
lived in Lexington, Kentucky. He was a guy who grew
up in Lexington, was enamored with the ponies, started going

(01:51):
to the tracks in Lexington, working in the stables, and
very quickly got connected to a lot of different people
who were within organized crime and were also just regular
horse betters, and very quickly learned that he had a
talent for betting on horses. He ultimately became known as

(02:14):
one of the best horse betters in the country, but
also started to help organize betting on sportes as it
was becoming more and more popular in the thirties and forties. Ultimately,
because members of organized crime and the leaders of organized crime,
they often came through Lexington to go to the tracks

(02:38):
and to vacation there. Like if you came through Lexington,
oftentimes you were also going to Arkansas where they had
the Springs Hot Springs Arkansas was famous for being a
casino town, a mini Vegas before Vegas, and a lot
of people would vacation there and get relief in the
hot springs and all this kind of stuff, right, All

(02:58):
this great just sort of really fun color about old
time betting history and betting stories. Anyways, Ed famously was
a bookmaker for the mafia and had this state in
Lexington where it had a secret room, and the secret
room you had to get to it by pressing a

(03:20):
button in his den, a wall opened up, and then
you could go down a spiral set of stairs into
the basement where he had literally dozens of phone wires
coming into the basement where he was working his operation,
running numbers and taking bets and moving money all across

(03:42):
the country like he was at the center of the
country doing this. It was insane. So I went to Lexington,
and I was lucky enough that I called the I
found the guy who owns his house randomly like through
various connections and phone calls reporting Matt shoe, leather, gumshoe,
That's what I do, right, So got in touch with

(04:03):
the guy. I land, I'm talking to guy for ten minutes.
I'm in Florida. I'm going to Lexington in two days.
I'm telling him what I'm looking for. He goes, why
don't you just come by the house. So I showed
up at the guy's house at nine point thirty in
the morning. Walks me in, never met the guy in
my life. Walks me in, total stranger. He goes, You're
not gonna believe this, walks me into the den, presses

(04:26):
the button, the wall opens up, takes me down the
spirdal staircase into the basement. It looks exactly the same.
They have not touched it. It is amazing. So that's
number one. I got to go and see a very
cool piece of sports betting history. What do you think
of that?

Speaker 2 (04:43):
Stranger? Let's you right into your right into the house. Incredible,
you're an America's guest and.

Speaker 1 (04:48):
Honest to god, I was shocked. And you know what's funny.
When I was down there, his wife comes down and
she's looking at me, and she looks at her husband.
He goes, now, honey, I did not check him out,
did not do one Google search. I just sort of
felt like I'm going with it and any here he is.

Speaker 2 (05:09):
Just this guy with his big gold full of whatever
exotic olive oils, eating macadamia outside of a little satchel,
He's no threat.

Speaker 1 (05:17):
He just sounded like such a sad sack, like if
he wasn't going to get into this basement, he might
not be able to write this book. So I'm just
gonna let him in. And he couldn't have been more lovely.
I'm not naming any names. I'm going to save it
all for the book. That's part number one. The other thing,
you know what, you tell your story and I'm going
to go back to something else I've learned incredible.

Speaker 2 (05:38):
Well, it's a testament to how unintimidating you are and
such a mensch that someone would meet you and go,
you know what, let me just take you over my house,
show you my secret rooms I'm burying you were, let
me take you to the fucking catacombs of my house.
It's no problem. You're trustworthy. You're wearing your little fedor

(05:59):
with your press little bit exact part in it.

Speaker 1 (06:02):
Yeah, yeah, yeah, honestly, God, it was great. I was
more than more than grateful.

Speaker 2 (06:09):
Well, Chad, I've got a treat for you today. I'm
going to tell you two stories featuring two absolute gambling
maniacs from the nineteenth century. I think they will resonate
greatly with our audience, who's also full of degenerates this
kind of aspirational behavior. So first person we're going to
talk about is brother Elijah Skaggs, the preaching Pharaoh Dealer. So,

(06:35):
as we've discussed in previous episodes, Chad, in the early
eighteen hundreds, they were like three gambling hotbeds. You had England,
specifically London. You had high end European resorts like the
German spa towns, and you had America. And in each
of these hot beds you had like one game that

(06:55):
was by far the most popular. In England, that national
game was has a dice game that would become basically craps.
In the European resort towns, they had my personal favorite
Roulette because I'm obviously very very classy. And in America
the national game was Pharaoh f a r o called

(07:17):
the Game that Won the West, and again not the
Ancient Grain, but a game a gamble game.

Speaker 1 (07:22):
Called which the Ancient Grain, which I just got to say,
it's making a comeback and it's so good for you
and it packs in so much nutrients I've been eaten
a lot of Pharaoh, and you can mix it. It's
great with olive oil. I just want to make that PSA.
I knew that get into the Pharaoh game. I knew

(07:45):
it would get you all hot and bothered. We talked
to ancient grains, even though so I you say ancient grains,
and all of a sudden, I'm in a different zone,
trying to.

Speaker 2 (07:55):
Try to control your emotions as we go through this.

Speaker 1 (07:58):
Uh.

Speaker 2 (07:59):
Now, the game rambling game Pharaoh, it seems like an
absolute blast chad. So like poker, you don't need a
lot of stuff, and unlike Roulette, you could play it
virtually anytime, anywhere. But like Roulette, it involves virtually no
skill whatsoever. And when you play Pharaoh, you play against

(08:19):
a dealer, and that dealer can be located in a
casino the way you'd like picture it when I say dealer,
but a Pharaoh dealer could also just be an independent person,
like an independent contractor, traveling from town to town. Because
everything you need to play Pharaoh fits in a single kit.
In America, these were typically small mahogany boxes, and on

(08:42):
the boxes would have a picture of a Bengal tiger
that was the symbol of Pharaoh. Inside these little boxes
was a layout. It was everything you needed. It was
a tray of chips and a deck of cards, and
like a little felt fold out that you just place
on a table and it would have pictures of the
thirteen different cards on it from two to ace. And

(09:02):
this is an audio medium, Chad primarily, So in the
spirit of painting a picture, I'm going to use you
as our model for the roving Pharaoh dealer. So you
Chad Norman. First, you learn how to deal Pharaoh. Next,
you get a little bankroll of cash or a partner
who has cash.

Speaker 1 (09:21):
Scet question, Yeah, go ahead in this in this play,
do I get a speaking role?

Speaker 2 (09:27):
Oh for sure? For sure. Yeah you'll be paid. Yeah,
you get paid. You'll get a union scale because you
have a speaking role.

Speaker 1 (09:33):
Just let me know when it's time for my line.
Because I got a I think I got one.

Speaker 2 (09:36):
Well, suddenly it's very easy for you to now start
going town to town as like a mobile casino. You
have your little cat. You get everything you need. Maybe
you make a deal with a local bar. Maybe you're
setting up shop in a hotel. Maybe you have a
little well maintained mustache. Maybe you're wearing a snappy little

(09:56):
vest with a little pocket watch. Maybe you look incredible.
Maybe you have a little phrase you say like, go ahead.

Speaker 1 (10:03):
Pharaoh, Pharaoh, get you Pharaoh.

Speaker 2 (10:10):
Perfect. Yes, you've nailed it. The way you avoided talking
about ancient grains and you're selling in your cell job
is perfect.

Speaker 1 (10:17):
Well, this is what I feel like. The reason I
said it is because it could be a little bit
of a bait and switch where I could get people
who are interested in gambling, and like I'm speaking to
the insiders and they're coming in and they're like, oh
my god, I get to play Pharaoh. How incredible is that.
But if they don't know, they could just be a
little peckish and be coming by for a bowl of

(10:39):
Pharaoh and they're hungry. I'll be like, oh no, I
mean the game. Let me show you. And then they're
so entranced by my sales job. All of a sudden
they're playing the game and I'm making bank.

Speaker 2 (10:51):
A natural salesman. So yeah, getting that out so quickly incredible.
We're truly painting a picture I could.

Speaker 1 (10:58):
Have survived by my in the late eighteen hundreds.

Speaker 2 (11:01):
So you and your wiles, you can head out west,
you can go down south, very easy for you to
find a place to set up shop because there's lots
of money in it, so people are happy to see
Pharaoh dealers. And I won't dive into the rules, but
like as a game, I'll just note that it's quiet,
it's fast, it takes up very little space, and it's

(11:23):
still very exciting. And best of all, you could be
saved and illiterate Old West Minor with like lead poisoning,
and you could still learn the rules and remember them
pretty easily. So it's it's really like a perfect game
for the era. So that's the backdrop. The stage is set.
Let's talk about our boy, Elijah Skaggs. So Elijah's born

(11:47):
and raised in backwoods Kentucky. It's part of a huge
extended family. Everybody's gambling, the whole family, the whole area.
So he learns how every game works. He loves it.
Who wouldn't. He eventually learns all the tricks of the trade.
He learns how to cheat as a dealer, stacking the deck,
bottom dealing all that stuff. By the time he's twenty one,

(12:09):
he's won a pile of cash off everybody he knows,
in town and he's like, you know what, I'm taking
my show on the road, and he understands strong personal branding,
Chad like you. He dresses in a plain black frock coat,
plain suit, white shirt, yeah yep, white shirt, high collar.
He looks a lot like a preacher, so he gets

(12:31):
the nickname the Preaching Pharaoh Dealer, which he loves because
he feels an almost religious zeal for this game because
the thing he loved most about it was it's a
game that's entirely in control of the dealer. If you
master the deal, you could control the entire game. So
Skekes packs up. First, he hits up Nashville that he

(12:52):
spreads out to all up and down the Eastern seaboard,
and if he ever catches a fellow dealer, toll in
the fast one that he's never seen, he bribes these
guys very handsomely to teach him because he's a lifetime
learner chat just like us, love of learning. He's traveling around,
he's cheating his way into a ton of money, but
he realizes he could only make so much as one guy,

(13:14):
and that gives him an incredible idea. Ched he goes
down to New Orleans. He sets up an operation, and
he's going to run America's first gambling syndicate.

Speaker 1 (13:24):
He's going to scale.

Speaker 2 (13:25):
That's right, that's exactly right. So Elijah goes into all
the casinos. He's looking for young gambling recruits. He gathers
them up, He teaches him. He trains them relentlessly on
how to cheat as pharaoh dealers, because he's very good.
So he's good, he's a good professor. Once these guys
are all trained up, he sets them up in teams
of two. But he then assigns every one of these

(13:48):
duos with one of his dozens and dozens of cousins
who serve as essentially the roving pit boss, and he
dispatches them all across the country. He pays all the expenses,
and the dealers can keep twenty five percent of what
they rake in after expenses. And it works, Chad Norman,

(14:09):
it works perfectly. At their peak, he had one hundred
dealers running this remarkable nationwide racket, and the money is
just pouring in. And what did you just say, what's
the first thing he does with the money?

Speaker 1 (14:23):
Chad gambles it.

Speaker 2 (14:25):
No, he scales, he scales the operation. He scales more.

Speaker 1 (14:29):
Okay, I was wrong.

Speaker 2 (14:30):
I'd be like, he's an incredible He'll we'll get to
the gambling in a second. But he's still an invest mode.

Speaker 1 (14:36):
He's a businessman.

Speaker 2 (14:37):
He is a businessman first. He funds his own gambling
house in New Orleans.

Speaker 1 (14:43):
Hire ahead, He's hire and ahead, he's getting ahead.

Speaker 2 (14:46):
He's got a brother. He wants to run a similar
racket out in California. And they're not even a state yet.
You could do whatever the fuck you want out there,
he goes. Sounds good. He bankrolls his brother to open
up an operation on the West coast. And I know
you'll like this. He's a patron of the gambling arts.
Chad Elijah funds inventors to help him cheat. He pays

(15:08):
inventors to fund new like gambling devices, new crooked pharaoh boxes,
and all sorts of stuff like that, and in return,
he gets exclusive usage for one year and then they
could sell to whoever they want. And that works too,
can't he can't stop making money. By the time this
guy is forty years old, his inventor pials have flooded

(15:30):
the market with crooked faraoh boxes. All those dealers are
known as cheaters. It doesn't matter. He's two decades into
this racket and he retires. This absolute son of a
bitch is a multimillionaire in the goddamned eighteen fifties converting
to today's dollars. Yet we're talking about a guy worth
like one hundred million dollars today just through cheating at

(15:53):
a huge scale. The classic corporate American success story. Herbert Asbury,
the journalist and bettic expert who wrote the original book
Gangs in New York. He said of Elijah Skaggs that
more than any other individual, he likely had the single
biggest influence on the spread of American gambling nationwide. This

(16:15):
guy was an incredible operator.

Speaker 1 (16:17):
I've got a nickname for him.

Speaker 2 (16:18):
Oh lay it on me.

Speaker 1 (16:21):
Elijah Skags, the scaling syndicate selling swindler.

Speaker 2 (16:32):
Incredible. See you got a literation, I mean a natural
author's brain, always working overtime.

Speaker 1 (16:38):
Check literate podcast.

Speaker 2 (16:39):
It's an incredibly literate podcast, and showed I'm sure you're
thinking house the story end? Does that have a happy ending?
Of course Skags enjoyed a luxurious retirement and then then
mid retirement he made his two biggest gambles. The first
was buying an enormous Louisiana cotton plantation, and the second

(17:00):
was investing millions and millions of dollars into that's right,
Confederate war bonds. So spoiler alert to any two hundred
year old listeners, the Confederacy would go on to lose
the Civil War, Elijah would lose his entire fortune, and
he died pretty close to penniless in Texas at eighteen ninety.
And that's the story of Elijah Skagg's America's Crooked Pharaoh King.

Speaker 1 (17:25):
Elijah Skaggs, gambling pioneer, scaling syndicate, selling swindler that.

Speaker 2 (17:35):
Are at war bonds not a good investment.

Speaker 1 (17:37):
Here's what's interesting, and it connects directly to my story
as I'm researching this book, is how so many businesses
today were born of illicit, ill gotten gains. Right. You

(17:58):
could look at the whole gambling industry and say this
is built on the back of illegal activity. Right. The
predominant purveyors of gambling products through the early nineteen hundreds
until the nineteen eighties was organized crime and the mafia.

(18:25):
And slowly but surely, as more and more states legalized
various forms of betting, that transitioned away from being the
dominant source of revenue for organized crime into being legitimate
businesses that have created Caesars, MGM, DraftKings, fandul Action Network. Right,

(18:49):
all of these used to be completely illegal businesses that
were dominated by organized crime. Professional sports, Matt, What if
I told you that some of the biggest brands in

(19:09):
professional sports were founded by sports beetters. What if I
told you that.

Speaker 2 (19:16):
Sounds like high risk tolerance zealotz ched Matt. New York Yankees,
I've heard of them.

Speaker 1 (19:25):
The New York Yankees founded by a man who was
known as a degenerate gambler who prominently fixed games. Was
so known for fixing games, he built what was at
the time the largest casino in New York on thirty

(19:46):
third Street in Manhattan. And people had to wonder, as
he's sitting in the casino, are the players also fixing
the game so he can continue to make money at
his casino? New York Yankees founded by a gambler? How
about the New York Football Giants still owned by the

(20:08):
Marra family. Tim Merra, famous famous better went to Belmont,
won five hundred dollars at the track the next day,
bought the New York Football Giants, Detroit Lions founded by
a gambler, Cleveland Browns founded by a gambler. Chicago Cardinals

(20:31):
still owned by the Bidwell family. Bill Bidwell famously a
gambler with significant hold on Was it Bill Bedwell or
was it Charles Bidwell?

Speaker 2 (20:43):
I don't want to defame any I think I think
Bill was the song.

Speaker 1 (20:47):
Yeah. Charlie Bidwell, former Cardinals owner, made a fortune opening racetracks.
Also he was Let me just make sure I get
this right. He was a known associate of al Capone,

(21:07):
non gambler, known racetrack owner Pittsburgh Steelers still owned by
the Rooney family. Art Rooney once famously won two hundred
thousand dollars betting on the horses, owned a saloon, allegedly
bought the Steelers with gambling winnings. What's interesting about this?

(21:28):
By the way, Lamar Hunt who obviously the Chief's founder.
He was the son of H. L. Hunt. HL Hunt
was an oil man in Texas. It is widely known,
like there are stories about this in I've got a
Newsweek issue of Newsweek from nineteen sixty that includes the

(21:48):
biggest sports betters in the world. H L. Hunt is
listed as one of those sports betters in the oil field,
at the poker Tales to tables everywhere else, very well
known as a sports better list goes on, Man, it's
amazing to me. And I think that your point is, Look,

(22:12):
when people were buying these teams and these professional leagues
were starting in the late eighteen hundreds early part of
the nineteen hundreds, it wasn't the Titans of industry. It
wasn't the Vanderbilt, it wasn't JP Morgan, it wasn't the
Rockefellers who were going to take their industrialist riches and

(22:34):
invest in these nascent sport leagues that were made up
of you know, blue collar workers and people who largely
weren't educated and were known as sort of people hanging
out in barrooms in Brawlin. They weren't going to invest
in these professional sports leagues. The only people who were

(22:56):
going to do it were sports freaks who were probably
betting and had a high tolerance for risk. And that's
why so many of these teams were founded by professional betters.

Speaker 2 (23:06):
And it could offer something that they you can't buy,
which would be a you know, bragging rights, a championship,
something that you'd have to, you'd have to earn your
way into which I think still happens to this day.

Speaker 1 (23:17):
Correct, give me one more story, Matt Mitchell.

Speaker 2 (23:20):
All right, this is the story of John Better Million Gates,
the most notorious big money gambler in American history. And
that's that's our buddy. Dave Schwartz so said with some authority.
So John Gates is an absolute degenerate, absolutely love to gamble.
If you look up, his face looks like it belongs

(23:41):
on us currency, looks like Rutherford B. Hayes. It looks incredible.
And one of my favorite things to do with this
stuff chat is learning how these old like gambling whales
how they get rich in the first place, because that's
a that's always interesting to me because he didn't come
from a wealthy family, and with John Gates, that's a
really that's a fun place to start. So just as

(24:01):
Eliza skags our boys buying his Confederate War bonds, our
guy John Gates is being raised on an Illinois farm
just west of Chicago, and he hates it. And if
any of those two hundred year old listeners of ours
are near you, they'd happily tell you he hated it.
Because it's hard and it sucks, like there's no mystery
about why working on that farm wouldn't be appealing. One summer,

(24:25):
he gets paid by a neighbor to clear some timber
from the property. Then he gets to keep the timber
and he cuts it up and he sells it as
firewood down at the railroad station. It's actually pretty savvy racket.
Get yourself paid twice, right. He hates that too, because
it's really hard and it also sucks. So eventually he's
hanging down so much down the railway that the railroad

(24:48):
workers are like, hey, do you want to come play
in our card game? And they teach you how to
play Pharaoh, which he likes right away because it is
very fun and pretty soon John's like, man, playing cards
is way better than working. I like this a lot more.
He gets good at playing poker, he wins some money,
and basically he's like, I'm not I'm not running this

(25:08):
work racket anymore. This sucks. Playing cards is way more fun,
which like, same, same dude, I feel you. Eventually, though,
he meets a nice girl, he has to get a
real job because you know, he wants to marry her
and all that can't just be a guy that plays
poker behind a locomotive. So after a couple fall starts,
he gets up. He's trying to run a hardware story.
It goes under. But when he's doing that, a salesman

(25:30):
comes in and introduces him to a brand new invention
called barbed wire. He sees this invention and he's like, man,
this shit is dope. Everyone's gonna need this. So he goes, Okay,
let's do it. I'm gonna I'm gonna quit the hardware
store and I'm should go do like this is this
makes perfect sense. He understands immediately the value. He goes,

(25:51):
I'm gonna go to work for one of these guys
that sells this. He goes down to Texas and all
the ranchers meet him and they're like, holy shit, John
Gates is incredible. He's just a degenerate like us that
wants to gibble with us all day. So he's becoming
very popular.

Speaker 1 (26:06):
And he's got bales of barbed wire.

Speaker 2 (26:08):
Well, here's the thing, Chad Gates new. These ranchers have
a big problem on their hands, right, and do you
remember Favorites contest winner Daniel from Bowbell's North Dakota very well.

Speaker 1 (26:20):
He was one of our highlights.

Speaker 2 (26:23):
I hope he's listening right now because he is an
absolute gem of a guy.

Speaker 1 (26:26):
Yeah.

Speaker 2 (26:27):
Do you remember what he spent his forty thousand dollars
prize money on tractor? I believe cattle. He bought cattle.

Speaker 1 (26:33):
That's right, that's right.

Speaker 2 (26:34):
So our pal Daniel would definitely have understood the problem
these ranchers are facing. They own tons of open range now,
which is kind of brand new. They need a way
to close in these enormous parcels of open land. They
need to keep livestock out of other people's crops because
that costs them money. They need to keep their livestock

(26:55):
off the fucking railroad tracks because that screws with everybody.
And that are miles apart from each other, don't get
it on. They don't produce enough cabs, so using any
normal fence material like wood would literally bankrupt ranchers. You
can't make a fifteen mile fence out of wood out there.
So Gates is like, great, I'll just explain this to

(27:16):
everybody in Texas and they are like, absolutely not. We
don't want any of your barbed wire. And they either
think it's some kind of trick, or that it'll hurt
their animals and it won't work, or that generally it's
just some kind of racket that Yankees are trying to
run on the South, because there's still a lot of
distrust there from any of you know, Yankee big ideas,
which I know you can't blame them, I get it.

(27:39):
So Gates stops playing cards. Elitist. It's an elitist in
degit exactly. So Gates stops playing cards for like one second,
and he's like, I've got an idea. I'm gonna make
this big, insane bat. He stages a cattle stampede in
Military Plaza in downtown San Antonio, which is still there
as like a public demonstration, and it proves that barbed

(28:02):
wire is a safe and effective tool that they can use,
and it works perfectly. He makes a fortune in sales,
and he goes to the owner of the company. He's like, hey,
I'm killing it. I want to go into business with you.
Let's be partners. The owner says no. He goes, all right,
I'm out. He goes to Saint Louis. He finds another
guy making barbed wire, and he says, hey, let's go

(28:25):
into business together. They sell even cheaper and they're killing it,
and eventually gates old boss sues them for using identical equipment,
and for the record, it was very similar, but it
was not identical anyway. Gates and his partner know that
if they get served papers, they're going to have to
shut down, and if that happens even for a little bit,

(28:47):
they're cooked. So they come up with another insane gamble.
While hiding for process servers, like in a bad nineties movie,
they rent a small building directly across the Mississippi. It's
their new headquarters, and in the middle of the night
they hire dudes to take all their machinery down to
the river, load it down to a ferry, push it

(29:09):
across the river, and dock it on the opposite bank
in East Saint Louis, Illinois, outside of the court's jurisdiction.
It pays off. They continue operating. They continue making barbed wire.
John Gates is a genius. Blah blah blah. Company gets huge.
They eventually merge with US Steel, owned by JP Morgan.

(29:29):
Gates becomes a bazillionaire and becomes enemies with JP Morgan,
the richest and most powerful person probably in American history,
which is another whole hilarious story. But that's how Gates
becomes this kind of loaded guy. Stock markets crushing he
and Vassi makes more money, and now now Chad he

(29:49):
can get out of his mind gambling. He is gambling
amounts of money that made me think, oh, that's just
how it was back then with these robber barons, and
the other robber barons are like, no, that's not how
this works. This is not how any of us are.
This is insanity, and I'm gonna show you how. First thing,
he's like, you know what, I'm gonna need a clubhouse

(30:10):
to gamble in. So he pays thirty thousand dollars a
year for a giant suite at the Waldorf Astoria in Manhattan.
He lives in Chicago, but he's like, I'm making money
in the stock market, it makes sense for me to
keep a place to Waldorf Astoria. The hotel hates his
guts because he's literally using it as a private gambling clubhouse.

(30:32):
The suite has a private entrance, private elevator, and still
the amount of noise him when his buddies are making
is like out of control. True robber baron Fat cat behavior.
This guy has a South side Chicago mansion that's still there.
It's just on the other side of the ninety Express
from raite Field where the White Sox play. Not where

(30:53):
i'd build my mansion today, but that's fine. He'd gather
up his Chicago buddies and they'd get on the train
to New York City to party at the Waldorf. And
there were reports that these guys would go on benders
where they'd play a cash poker game for four uninterrupted
days and nights. They'd start in Chicago at the train station,

(31:14):
they play for the two day overnight train ride, they'd
freeze the game, they'd move into the suite at the Waldorf.
They played two more full days and nights with millions
of dollars changing hands, huge amounts of money. And I'm
looking to see, like, oh, I'll paint the picture. I'll
look up where it was taking place. This is as
they're still planning Union Station and Grand Central Station. That's

(31:35):
how long ago this was. His wife obviously knows she
married a fucking gambling demon, but she reportedly didn't like it,
like these week long gambling free for alls were like
that's a little much for her. So she tried to
break them up. But instead of just trying to limit
these benders to like a couple days, Gates learned a
trick that I think I assume you've done several times, Jed.

(31:57):
Let me know if this sounds familiar. In a soon pocket,
he'd keep a few giant, loose diamonds, and if his
wife was really mad at him, he just fish went
out and say, hey, honey, I just won this, why
don't you do something nice with it? And she'd just
walk over to Tiffany's and they'd have it sat and
that would usually buy him like a day and a half,
just like you would say.

Speaker 1 (32:18):
That's that's how we live, Matt.

Speaker 2 (32:21):
Yeah, I mean everyone needs to buy time. Everyone's time
is valued in a different way, Chad.

Speaker 1 (32:27):
Except instead of diamonds, I give her bowls full of farah.

Speaker 2 (32:32):
Yeah.

Speaker 1 (32:33):
Yeah, you know that's my vote language.

Speaker 2 (32:36):
You're so mad at me. It seems like you're hungry,
but you don't want the bloat. Have I got great
news for you? There are reports of him betting the
equivalent of one hundred thousand dollars on coin flips multiple times.
He won it close to a million dollars out a
single horse race, which is how he got the nickname

(32:56):
Bet a Million Gates. There's no indication he would actually
good at betting on the ponies, but the president of
the jockey club eventually asked him to please limit his
bets to ten thousand dollars a race because the sheer
scale of his wagers was starting rumors that the races
were fixed. And when our guy, Dave Schwartz calls him

(33:17):
the most notorious big money game, blurred history, like, that's
the kind of behavior that earns that title. When operators
are like, bro, you are betting so much money, all
reasonable people are thinking this guy must be cheating, because
what is happening is like unimaginable. But I'm gonna end
the story of John Gates with my favorite anecdote, because

(33:37):
he bets on something so insane that I never even
considered it. On at least two separate, fully witnessed occasions.
Once on a train ride from Chicago to Pittsburgh and
again in a clubroom at the wald up Astoria, John
Gates and another man bet the modern equivalent of almost
one million dollars on which of two rain drops on

(33:58):
a window go to the bottom of the window first
both times. Gates one, and that's the story of John
bet a Million.

Speaker 1 (34:08):
Gates, John bet A Million Gates, Elijah Skaggs, two Americans
infamous for their ability to wager insane, uncomfortable amounts of money.
Matt Mitchell as always bringing the color, bringing the flavor,

(34:29):
bringing the Pharaoh directly to our listeners. The Favorites will
return with our next episode on Tuesday on the Action
Network YouTube page. We're talking NBA draft. Downloads from Spotify,
Apple Pods wherever you get your pods, Rate review, subscribe,
we use five stars, say whatever we want. Feedback is
a gift. Until next time.

Speaker 2 (34:50):
I Love you.

Speaker 1 (34:59):
Action Network reminds you please gamble responsibly.

Speaker 2 (35:03):
If you or someone you care about has a gambling problem,
help is available twenty four to seven at one eight
hundred gambler
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Hosts And Creators

Colin Cowherd

Colin Cowherd

Jason McIntyre

Jason McIntyre

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