Um, you know, there is this very specific rhythm
to modern travel that I think we all just sort
of accept now. Oh, absolutely. The rushing, the
waiting. Right. Yeah. You're rushing through
the terminal. You're constantly checking your
watch. You're desperately looking for a place
to charge your phone. And, uh, if you fly through
Chicago, you see this one thing everywhere. You're
talking about the letters. Yes. It's stamped
on your luggage tag. O -R -D. It's on the highway
signs. It's painted on the walls. O 'Hare. I
mean, it is one of the busiest airports on the
planet. Something like 80 million passengers
pass through there in a typical year. It's essentially
a city within a city. Exactly. And I would bet
that 99 % of those 80 million people never really
stop to think about the name. It's just a word
to them. You know, I'm flying into O 'Hare. But
if you do happen to ask someone, hey, who is
this O 'Hare guy? They usually have a vague idea.
They'll say, oh, it's named after a war hero.
And well, they wouldn't be wrong. The airport
is named after. Edward Butch O 'Hare. He was
a naval aviator who won the Medal of Honor in
World War II. A completely legitimate, bona fide
hero. Right, but here is the twist for today's
deep dive. That is not why we are here, because
behind that war hero there is a much darker,
honestly much more complicated story. We are
diving into a biographical overview today, not
of Butch, but of the man who made him. We're
talking about his father, Edward J. O 'Hare.
also known in the history books by a very different
name, Easy Eddie. Easy Eddie. I mean, the name
alone sounds like a character straight out of
a noir film. It really does. And looking at the
source material you've pulled together for this
deep dive, his life really was a noir film. We
are talking about a guy who lived a double life
in the truest sense of the word. It's the absolute
definition of a double life because on the surface,
he's this high flying, very wealthy lawyer. He's
making an absolute fortune in the Greyhound raising
business. He's a pillar of his community in St.
Louis and later in Chicago. Right. But just below
that surface, he is the attorney and a key business
partner for arguably the most famous gangster
in American history. Al Capone. And that is the
hook for me. That is the mission of our deep
dive today. How do you go from being a lawyer
for the Chicago mob to being the secret undercover
informant who helps bring the entire outfit down?
because that is where the story goes. He helps
the feds destroy Capone's empire. And he pays
the ultimate price for doing it. So we have a
lot to unpack here for you today. We've got the
mob. We've got mechanical rabbits. The rabbits
are the best part. They really are. It's my favorite
detail. And we have this deeply tragic father
son dynamic. But let's rewind a bit. Before the
giant international airport, before the mob hits,
who was Edward J. O 'Hare? So his story starts
a big south of Chicago. He was born in St. Louis
in 1893. And it's a fairly classic American origin
story for that time. He had first generation
Irish -American parents. And by all accounts
in the sources, he was just incredibly ambitious
from day one. He passes the Missouri bar exam
in 1923 and immediately joins a law firm. OK,
so that's a standard lawyer track so far. He's
grinding. He's passing the bar. But this is where
I got completely stuck in the notes. Because
usually, when you hear the phrase mob lawyer,
you assume the money came from bootlegging or
protection rackets right out of the gate. But
Eddie's first fortune actually comes from a rabbit.
A mechanical rabbit, yes. Please explain this
to me because it sounds absolutely ridiculous.
It does sound funny to us now, but you have to
put yourself back in the context of the 1920s.
This was basically high tech stuff back then.
O 'Hare represented an inventor named Owen P.
Smith, and Smith was the High Commissioner of
the International Greyhound Racing Association.
Wow, that is a very lofty title. It is. And Smith
held the patent on the mechanical rabbit. You
know, the little lure that zips around the track
that the dogs chase. Wait, so before this invention,
did they just use a real rabbit? Often, yes.
Or the racing was just much more chaotic and
harder to organize. The mechanical lure completely
revolutionized the sport. It made greyhound racing
a massive scalable industry. You could suddenly
run races on a strict schedule night after night
without fail. And because O 'Hare represented
the inventor, when Smith died, O 'Hare ended
up representing the administration of the estate.
Which means he essentially controlled the patent.
Correct. He controlled the rights to the core
technology that made the entire sport possible.
This gave him a massive foothold in the industry.
So by 1925, O 'Hare isn't just a lawyer anymore.
He is actively operating dog tracks in Chicago,
Boston, and Miami. And we aren't talking about
just Paying the bills money here, we are talking
about serious wealth. Oh, absolutely. The biographical
overview paints a very vivid picture of the O
'Hare lifestyle in St. Louis before they made
the full move to Chicago. They live in the Holly
Hills neighborhood. They had a brand new house.
And get this, the house featured a swimming pool
and a private skating rink. A private skating
rink in the 1920s. Yeah. That is a level of wealth
that is just hard to comprehend for that era.
It was a life of extreme privilege. To escape
the St. Louis humidity in the summers, they spent
their time at these sprawling river camps on
the Meramec and Gasconade rivers. They had servants,
luxury cars, the whole works. He was living the
American dream. turbocharged. But here's the
thing that strikes me about his personality.
You see this guy with the skating rink and the
country clubs, and you think, OK, he is spoiling
his family. He's the fun, rich dad. But the notes
on his parenting style suggest something totally
different. He wasn't just writing checks and
ignoring his kids. No, not at all. And this is
crucial to understanding the future war hero
Butch. E .J. was absolutely obsessed with discipline.
There is this famous anecdote in the sources
about his relationship with his son, Butch. It
is often referred to as the lazy incident. Yeah,
I loved this part. It is so relatable, yet his
reaction is just so extreme. Right. So one day
in the 1920s, E .J. comes home after a long day
of lawyering and track management, and he finds
his son, Butch, sprawling on the couch. Now,
Butch is reading books which you would think
a lawyer dad would appreciate. But he's also
just stuffing his face with banana layer cake
and donuts. I mean, to be fair, reading books
and eating donuts sounds like a pretty ideal
Saturday to me. Oh, to you or me, sure. But to
a driven man like EJ, a guy who is clawing his
way up the ladder of wealth and power, this looked
like the end of the world. He saw it as a massive
sign of weakness, laziness. He looked at his
son and thought, he's getting soft. So what does
he do? Does he ground him, take away the banana
cake? He goes nuclear. He decided right then
and there that he wasn't having it. He immediately
enrolled Butch in the Western Military Academy
in Alton, Illinois. Just because he was eating
donuts on the couch. Because he was too comfortable.
E .J. wanted to toughen him up. And ironically,
that military school is where Butch started to
develop the intense discipline that would define
him later in the Navy. It wasn't really a punishment
in E .J.'s eyes. It was a necessary course correction.
There is another connection here between father
and son that I think is vital for you to know
because the airport isn't named O 'Hare just
because the dad was a wealthy lawyer. It is because
the son was an incredible pilot. But that obsession
with flying that started with the dad. It did.
E .J. was completely fascinated by aviation.
You have to remember this is the golden age of
flight. Lindbergh. The whole world was looking
up at the sky. And E .J. actually hitched a ride
in a mail plane with Charles Lindbergh at one
point. That is a serious claim to fame, flying
shotgun with Charles Lindbergh. And he didn't
just ride along. He even took a job for a while
as the lead pilot for an airmail route operated
by Robertson Aircraft Company. Wait, pause. So
he is a lawyer. He runs multiple dog tracks.
He has a private skating rink in his house. And
he is flying commercial airmail on the side.
He was a man of many, many talents. And he made
sure Butch had those talents, too. He got butch
flying lessons long before most kids would ever
be near an airplane. He gave him a .22 rifle
to practice shooting at floating cans in the
river to improve his marksmanship. He was essentially
engineering a hero. He was building the exact
skill set that Butch would later use to earn
the Medal of Honor. It is almost like he was
preparing him for a war he didn't even know was
coming. But while he is building this perfect,
disciplined son, his own life starts to pivot
into the shadows. Because in 1927, everything
changes. He divorces his wife, Selma, and moves
to Chicago full -time. And this is where the
Easy Eddie persona really takes over. When he
gets to Chicago, the Greyhound business naturally
brings him into orbit with the people who can
gambling in the city. And in late 1920s Chicago,
that means one person, Al Capone. The Chicago
outfit. Correct. The outfit ran everything. The
rackets, the bootlegging, the gambling. O 'Hare
and Capone start collaborating. It wasn't just
that O 'Hare was his lawyer, they became actual
business partners. So this is his second fortune.
First the mechanical rabbit, now the mob. Exactly.
And this is where he earns the nickname Easy
Eddie. He was slick, he was highly effective,
and he made legal problems simply go away for
the mob. He knew the law better than the gobs
did. But I want to pause on his personal life
here for a second because there is this wild
contradiction that I think really explains who
he was. Oh, you're talking about the engagement.
Yes. So in Chicago, he gets engaged to a woman
named Ursula Sue Granada. She is a secretary,
but she is connected. Her brother was a mob -affiliated
Illinois state representative, so he is dating
directly into the life, too. But the engagement
lasted for seven years. Seven years? He is a
wealthy mob lawyer. He can do whatever he wants.
Why would he wait seven years? Religion. O 'Hare
was a devout Catholic. Hold on. Let me get this
straight. He is actively working with Al Capone.
He is arguably helping to cover up murders, extortion,
racketeering. But he is worried about church
doctrine regarding marriage. People are complicated,
and O 'Hare was more complicated than most. The
Catholic Church wouldn't recognize his divorce
from Selma, so he was actually waiting. hoping
for a special dispensation from the Vatican so
he can marry Ursula legitimately in the church.
That is quite the mental compartmentalization.
I can launder money for a ruthless crime boss,
but I cannot get married without the pope's permission.
It creates a fascinating psychological profile.
He had these stripped moral codes in some areas
like parenting and religious marriage and complete
total flexibility and others like organized crime.
But eventually those compartments collide. You
can't keep them separate forever. Which brings
us to the pivot, the moment the movie would be
based on. In 1930, Yeezy Eddie decides to turn
on Al Capone. It is a massive decision. You have
to understand the stakes here. You don't just
quit the Chicago outfit, and you certainly don't
become an informant against them. Do the sources
tell us why? Was it a sudden crisis of conscience?
Was he trying to protect Butch's future? The
sources don't give us a diary entry where he
spills his soul, unfortunately. But we can strongly
infer that he wanted to clean up his legacy,
perhaps specifically for his son. He realized
he couldn't be the father of a distinguished
military man if he was the lawyer for a villain.
But he didn't just walk into a police station.
He was smart about it. He reached out to a reporter,
John Rogers from the St. Louis Post -Dispatch,
to set up a secret meeting with the IRS. The
IRS, because that was the ultimate strategy,
right? Capone was too slippery for murder or
bootlegging charges, so they were going after
his money. Precisely. Tax evasion. Rogers set
up a meeting between O 'Hare and IRS agent Frank
J. Wilson. And once O 'Hare was on board, he
didn't hold back at all. Agent Wilson later said,
and I quote from the source, on the inside of
the gang, I had one of the best undercover men
I have ever known, Eddie O 'Hare. That is incredible
praise coming from the people whose job it was
to put you in jail. But what was he actually
doing? Was he wearing a wire? Did they even have
wires back then? Not a wire. He was providing
something much deadlier to an accountant context.
He showed the feds exactly where the bodies were
buried financially speaking first He directed
agent Wilson to the specific bookkeeper who ultimately
became the key witness of the trial and more
importantly He helped the feds break the outfits
codes the codes Yes Capone's bookkeepers used
coded entries in the ledgers to hide where the
money was actually coming from to an outsider
even a highly trained federal accountant it just
looked like gibberish. O 'Hare translated for
them. He showed them the money trail. He would
point and say, this entry here, that's gambling
income. This entry here, that's bootlegging.
So he is literally the decoder ring for the federal
prosecution. Yes. But his absolute His biggest
contribution was even more dramatic. It plays
out exactly like a scene from The Untouchables.
Oh, wait. Is this the jury -tampering incident?
It is. And actually, if you have seen the 1987
movie The Untouchables, this specific scene is
in there, though they've shuffled the characters
around a bit for Hollywood. So set the scene
for us. This is the trial of the century. It's
October 1931. The trial is just about to start.
Al Capone is sitting in the courtroom, and he
is smiling. He is completely relaxed. He is cracking
jokes with his defense lawyers. He is confident.
Why? Because he knows the fix is already in.
He has successfully paid off or threatened the
entire jury pool. He knows for a fact he is walking
free. And O 'Hare knows this too. O 'Hare finds
out about the bribe and he immediately pips off
the government. He gets the word to the judge,
James Wilkerson. So just before the trial officially
begins, Judge Wilkerson walks into the courtroom.
He looks at the jury box, then he looks at the
bailiff. And he does something totally unprecedented.
He orders the bailiff to switch the entire jury
panel to another panel from a completely different
federal trial that was happening right down the
hall. I would pay very good money to have seen
Capone's face in that exact moment. He must have
been completely stunned. The color probably drained
right out of him. He went from a guaranteed acquittal
to suddenly facing a jury of total strangers
he hadn't bribed and didn't know. And that was
the nail in the coffin. Capone was found guilty
and sent to federal prison. And Easy Eddie was
the secret architect of that surprise. He effectively
ended the reign of the biggest gangster in the
world. He did. But there is a very strict rule
in that world. Snitches get stitches. Or in this
case, much worse. Right. You don't betray the
Chicago outfit and just retire to a beach in
Florida? No. No, you do not. So let's fast forward
a bit. Capone goes away to Alcatraz. O 'Hare
keeps living his life, probably looking over
his shoulder, maybe hoping enough time has passed
that they forgot. But then we get to 1939. The
timing here is incredibly suspicious. It is November
8, 1939. Al Capone is scheduled to be released
from Alcatraz in exactly one week. One week,
so the boss is finally coming home. Exactly.
The timing sends a very clear message. O 'Hare
is 46 years old at this point. He leaves his
office at Sportsman's Park Racetrack in Cicero,
Illinois. He gets into his car, which is a 1939
Lincoln Zephyr coupe. A beautiful, fast car.
And he is driving down the street. He approaches
the intersection of Ogden Avenue and Rockwell
Street in Chicago. Suddenly, a dark sedan pulls
up right alongside him. And this isn't a friendly
roll down the window and chat situation. I am
guessing not. There were two gunmen in the dark
sedan. They were wielding shotguns. And they
didn't just fire regular buckshot. They fired
a volley of what the source material specifically
calls big game slugs directly into the Lincoln.
Big game slugs, like ammunition meant for hunting
bears. Yes. They were not taking any chances
whatsoever. They wanted to completely shred that
car. O 'Hare died instantly. His car crashed
into a roadside post. The killers just kept driving
eastbound on Ogden Avenue and disappeared into
the Chicago traffic. That is just brutal. It
is a calculated execution. It was a message.
It was the mob loudly saying, we don't forget.
And there is a detail in the police report that
really gives me chills when I think about it.
When the police investigated the crash site,
they found something in O 'Hare's pocket. They
did. He was carrying a Spanish -made .32 caliber
semi -automatic pistol. and it was freshly cleaned
and oiled. Was that normal for him? Was he a
guy who was always packing heat? No, the sources
say it was highly unusual for him to carry a
weapon like that. It strongly suggests he knew.
He felt the walls closing in. Maybe he knew that
with Capone getting out in a week, the loose
ends were finally being tied up. Did he ever
get to use it? No. He never even had a chance
to draw it. The shotguns were too fast. And did
they ever catch the guys who did it? No arrests
were ever made. It remains an unsolved murder
in Chicago, although everyone historically knows
it was the outfit that's one of those open secrets
of history. It is such a tragic end. He helps
put away the bad guy, and a week before the bad
guy gets out, he is erased. And yet his legacy
is so much bigger than just that murder. And
this brings us right back to where we started
today, the airport. Right. Because while O 'Hare
is dying in a Lincoln Zephyr in Chicago in 1939,
what is Butch doing? Butch is using the skills
his father paid for and pushed him to learn.
He is in the Navy. And just a few years later,
in 1942, Butch O 'Hare becomes a national icon.
He single handedly defends his aircraft carrier,
the USS Lexington, against a wave of Japanese
bombers. He shoots down five enemy planes in
a single flight. Earning the Medal of Honor.
And eventually having the massive international
airport named after him. But you can't really
separate the two men. The father's dirty money,
the father's obsession with aviation, the father's
strict discipline that forced Butch into military
school. All of that paved the way for the son's
heroism. It is almost biblical when you think
about it. The father sins so the son can be a
saint. That is a very poetic way to put it. It
is like the father walked through the mud so
the son could fly. Without the Greyhound tracks,
without the mob connections, maybe Butch never
gets those expensive flying lessons. Maybe he
is just a guy reading books and eating donuts
on a couch in St. Louis. That is a wild thought.
And pop culture hasn't entirely forgotten Easy
Eddie either, right? No, it hasn't. If you watch
Boardwalk Empire on HBO, there's a character
named Mike D 'Angelo in the final season. That
character is heavily based on O 'Hare. They show
him as an undercover agent helping to get Capone
on tax evasion. And I saw a really weird reference
in the notes. He is mentioned in a book about
giant sharks. Yes. Meg, a novel of deep terror.
Apparently, there's a chapter called Payback
that recounts the story of Easy Eddie and his
son. It is a very odd place to find a historical
mob anecdote in a sci -fi book about a prehistoric
shark, but it just shows how compelling the story
is. It sticks with people. And the case isn't
entirely dead, history -wise. Even recently,
people have been poking around. True. As recently
as 2010, a Chicago alderman named Ed Burke actually
asked the police to reexamine the murder. There
was a book published called Get Capone that made
some new allegations, and they wanted the Colquay
Squad to take another look. It doesn't look like
it led to a definitive conclusion or any arrests,
obviously, but people are still asking questions
about who specifically pulled the trigger that
day. So when we step back and look at the whole
picture, what do we make of Edward J. O 'Hare?
Is he a villain? Is he a hero? I think the best
word is duality. He was a man who operated illegal
dog tracks. He served the mob. He was completely
comfortable with corruption. But he was also
a man who deeply valued discipline, who clearly
loved his son, and who ultimately risked and
lost his life to assist the federal government.
He is a reminder that history isn't usually black
and white. It is mostly gray. Exactly. He did
terrible things and he did one massive good thing.
and he probably did them both for the exact same
reason to provide for and protect his family.
It leaves you with a really haunting crudden,
doesn't it? When O 'Hare put that cleaned, oiled
.32 pistol in his pocket that morning in November
1939, do you think he knew his time had run out?
And more importantly, do you think he felt that
his contribution to jailing Capone balanced the
scales of his life? That is the ultimate question.
We will never know what he was thinking in those
final moments, but we certainly know what he
left behind. So the next time you are sprinting
through a terminal at O or D, maybe take a second,
look at the name on the wall and think about
Easy Eddie. The man who bet on Greyhounds flew
with Lindbergh and took down Al Capone. A truly
fascinating slice of history hidden right behind
an airport code. Absolutely. Thanks for taking
this deep dive with us today.