Case File | The Diamond Heist Sweethearts

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From Airship, I'm Jeremy Schwartz, and this is American Criminal.

Not all thieves are cut from the same cloth.

Though they're all out for themselves, every thief has their own goals, their own methods, and most importantly, their own limits.

For plenty of criminals, there are lines that you just don't cross, even when faced with the prospect of prison, or worse.

Take Diamond Doris Payne, for example.

In her decades-long career, she showed how far a thief could go without resorting to violence at all.

In the 1950s, she turned to crime, looking for the respect and independence that society denied her as a black woman.

She came up with all kinds of justifications for her misdeeds, but she never wanted to hurt her victims.

Instead, she made herself into a master of deception, employing a dazzling personality and sleight of hand to steal from jewelers in broad daylight without them even noticing.

She traveled the world and designed her clothes, stayed at exclusive hotels and pocketed diamond necklaces without ever drawing a gun.

It was an intoxicating world that she found impossible to give up.

But Doris Payne's only one kind of thief.

Worlds away from her are the offenders who don't even seem to inhabit the same reality as the rest of us.

People so violent and impulsive that long-term plans never really factor in.

They are pure id, all desire and adrenaline.

Men like Roger Reese Whittemore.

In the heart of the Flapper era, Roger Whittemore and his wife, Margaret, affectionately known as The Tiger Girl, recruited a dream team of hardened thieves.

The Whittemore Gang committed a slew of violent robberies in New York.

But unlike Doris Payne, the gang never bothered to cover their tracks.

Instead of relying on stealth and subterfuge, instead of careful planning and rapid escapes, they just killed anyone who got in their way.

This penchant for murder should have given the Whittemore Gang a reputation for being violent thugs.

But their exploits actually earned them near celebrity status.

Headlines about Roger Reese and The Tiger Girl sold papers.

And so they got a lot of attention, for better and for worse.

In time, all that hype would help detectives follow the bloody trail the gang left in their wake and finally bring them undone.

The stories of Doris Payne and the Whittemore Gang have a lot of similarities and a lot of differences.

But despite the things that set them apart, they're both wild rides from beginning to end.

From a master of manipulation to a gang of the rowdiest murderers of the roaring 20s, this is The Diamond Heist Sweethearts from Noiser's podcast, Detectives Don't Sleep.

It's Friday, February the 20th, 1925, in Baltimore, Maryland.

We're at the Maryland State Penitentiary and the Prison's Shoe and Boot Workshop.

In this era, the state pen is run as an industrial facility.

There's an iron foundry, a print shop, carpet weaving and clothing factories, as well as workshops for stone cutting and license plates manufacture.

Not to mention the chain gangs.

They get taken out to break rocks and build roads.

The prisoners are a cheap and freely available resource that the authorities farm out to private enterprise.

Health and safety?

That's not a priority.

24-year-old inmate Richard Reese Whittemore knows all about the injuries you can sustain working in this place.

It wasn't so long ago that he burned his arm on the electric iron used to smooth out shoe leather.

The wound still hasn't healed, and he has to go every afternoon to the prison hospital to get the dressing changed.

What the guards don't know is that the injury was self-inflicted.

You see, this is Whittemore's second stretch in the Maryland pen.

He knows his way around the prison, and he knows that the hospital is the weakest link in the prison security, which is why he deliberately burned himself and made sure it was bad enough to need hospital treatment.

After serving his first sentence, Whittemore had been on the outside for less than a year before he was incarcerated again, and now he's facing 15 years for his part in the armed robbery of a diamond salesman.

There's no way he's going to spend the next 15 years ironing shoe leather.

He's got a wife on the outside, Margaret.

She's a good-looking girl.

He tortures himself thinking about what she's getting up to while he's behind bars.

Just after 2 p.m., the door to the shoe workshop opens.

Willie Green, the trustee assigned to take Whittemore to the hospital, comes in.

A trustee is a prison inmate who's shown himself to be reliable and earned extra privileges.

Whittemore puts down his iron and goes with Green.

As they cross the yard, Whittemore sees a pile of building waste waiting to be cleared.

Green is walking a few paces in front with his back to Whittemore.

Whittemore quickly checks the guard at the next checkpoint.

He's looking away.

So is the guard behind him.

This is his opportunity.

Hardly missing a beat, Whittemore scoops up a length of metal pipe which he tucks into the leg of his cover hose.

No one saw him.

They reach the gate to the hospital.

It's manned by a 60-year-old guard called Robert Holtman.

Now Holtman is one of those avuncular types who is friendly with the inmates.

Last time Whittemore was inside, he worked at the hospital.

He and Holtman got along pretty well.

Whittemore knows how to make people like him when he wants to.

And Holtman, he fell for his charm.

Holtman lets Whittemore in with a nod.

Now Whittemore climbs the stairs.

The guard on each floor shouts, come it up as he passes.

He reaches a ward on the third floor.

The nurse is expecting him.

He pulls up his sleeve for her to examine his burn.

It's the last time I'm going to have it dressed, he says.

I'm going to give it the open air treatment.

He tuckles to himself at his little private joke.

After the nurse has changed the dressing, Whittemore makes his way back downstairs.

This time the guard shouts, coming down.

Finally he reaches the ground floor where Holtman is stationed.

There's another man there now, a trustee with a mob cleaning the floor.

But Whittemore isn't going to let the man's presence get in the way of his plans.

The guard, Holtman, has his back to Whittemore as he unlocks the gate.

It's now or never.

Whittemore slips out the pipe and brings it down on Holtman's head.

There's a sickening crack.

Holtman falls to the ground, blood streaming from his wound.

Whittemore takes the keys from Holtman's hand, then relieves the unconscious man of both his wallet and his gun.

In the next second, Whittemore has the gun trained on the trustee.

You'd better keep your mouth shut, he warns him.

Whittemore weighs his gun for the other man to move it.

He sticks the barrel in his back and pushes him forward to the next locked gate, which happens to be unmanned.

It's the last obstacle in Whittemore's way.

Whittemore opens the gate with Holtman's keys.

Then, he takes the last few steps to freedom.

Somehow the air tastes sweeter here.

As Whittemore runs along Madison Street away from the prison, he can hardly believe how easy it was.

Meanwhile the trustee heads back inside.

Yeah, he could have run away too, but he's concerned about Holtman.

When he sees the veteran guard lying unmoving on the floor, his concern turns to fear.

Holtman's dead!

He screams.

Actually, he isn't, but he will be in a couple of days.

Whittemore's escape from the Maryland State Penitentiary sets in motion a 12-month spree of violent crime.

They'll be hunted by detectives from three jurisdictions, but the determination and resourcefulness of one man, Inspector John D.

Coughlin from the New York State Detective Division, stands out.

The integrity and determination of New York's finest will be pitted against the ruthless depravity of a heartless killer.

And believe it or not, the American public takes the killer's side.

My name is Mark Dodson, and welcome to Detectives Don't Sleep.

Each week, we'll shadow the world's most remarkable sleuths, real detectives who worked extraordinary cases.

In this episode, a gang of violent criminals carries out a string of daring daylight robberies.

The gang is led by Richard Whittemore, aka, The Candy Kid.

His wife Margaret, or Tiger Girl, as she becomes known, is his devoted sidekick.

But one man is determined to stop him, the tough but principled New York cop, Inspector John Coughlin.

From Noiser, this is The Diamond Heist Sweethearts, and this is Detectives Don't Sleep.

Now, regular listeners will know, this show is all about the detectives.

But for once, we're going to start by looking at the villains of the piece, with a deep dive into the life and violent times of the candy kid and tiger girl.

Trust me, it's a hell of a story.

For all their misdeeds, Whittemore and his wife will be celebrated as folk heroes, a deadly duo who become America's twisted sweethearts, a decade before Bonnie Parker and Clyde Barrow capture the public's imagination.

They are the Scott and Zelda Fitzgerald of armed robbery.

But as you've already heard, Whittemore doesn't care who he hurts to get what he wants.

Margaret's no angel either.

She's not just happy to live off the proceeds of her husband's violent crimes.

She takes an active part in them.

So why do people love them so much?

To answer that question, you have to understand the times in which they live.

The era that made them who they are.

The Roaring Twenties.

The First World War is over.

Everyone just wants to put the misery of that conflict behind them and have a good time.

Scandalous dance crazes sweep the country.

A new breed of woman, the Flapper, is living life according to her own rules.

The Hollywood Dream Factory is in full swing.

And at those wild Tinseltown parties, the drugs are flowing too.

The soundtrack to it all is a startling new music with an irresistible rhythm.

This is the Jazz Age, a time of excess and conspicuous consumption.

But it is also the decade of Prohibition.

Practically overnight, the production, distribution and sale of alcohol becomes illegal in every state in America.

And while drinking alcohol itself isn't a crime, it's hard to get ahold of stuff without dealing with criminals.

The law becomes something that even formally respectable people choose to ignore.

In other words, criminality becomes socially acceptable.

Of course, there is a spectrum of lawlessness, and Richard Reese Whittemore places himself at the most extreme and violent end of it.

Whittemore's family background gives no indication of the direction his life would take.

Once, the Whittemore name meant something in their hometown of Baltimore.

Previous generations had a reputation for hard work and public service.

Richard Whittemore turned his back on all that.

He didn't want to work hard.

He didn't want to help others.

He just wanted to take what was his and to hell with anyone else.

His father blamed his waywardness on an accident at the age of two.

The kid fell out of a window and banged his head so badly, it caused seizures.

Now, this might seem like a desperate parent clutching its straws, but a study in the 1990s indicates a link between traumatic brain injury in childhood and the onset of psychopathy.

Maybe there's something in it.

Whittemore grew up in a typical row house in a working class district of West Baltimore.

Margaret Messler, two years his junior, was a neighbor.

They went to the same schools and were childhood sweethearts.

Margaret seemed to have a thing for bad boys, and Whittemore, he was the baddest of them all.

So Whittemore's first brush with the law was at the age of ten, when he was charged with firing a gun in a public place.

As an adolescent, he saw the inside of various juvenile correctional institutions.

In 1918, age 17, Whittemore enlists in the Coast Guard while on the run from reform school.

His time in the military service doesn't end so well.

A dishonorable discharge is followed by a spell in New York's notorious Elmira Reformatory.

Whittemore later describes the place as a school for crime.

On his release, Whittemore returns to Baltimore, where he rekindles his relationship with Margaret, all grown up now.

The couple marry in 1921.

She's 18 and he's 20.

On just eight days after they exchange vows, Whittemore and a buddy break into a neighbor's house and walk away with a suitcase full of stolen gear.

Unfortunately for them, a witness sees them.

When the police come calling, Whittemore owns up to the crime and begins his first stretch inside the Maryland State Penitentiary.

It's there that he meets the older, more experienced criminals, Leon and Jacob Kramer.

The brothers are impressed by Whittemore's bravado and take him under their wing.

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Whittemore keeps his nose clean and is released in April 1924, after just 3 years.

He returns home to his wife, Margaret.

Almost immediately the couple go into the armed robbery business together, with Margaret pulling a gun on a young sales girl in a candy store.

The stunt earns her the nickname The Bob Haired Bandit, on account of her fashionable hairstyle.

The Tiger Girl tag comes later.

In October 1924, Whittemore and some associates hold up a jewelry salesman in Philadelphia.

One of those associates is picked up by the police and rats out Whittemore, who finds himself back inside Maryland State Penitentiary, facing a 15-year stretch.

He gives him a chance to resume his acquaintance with the Kramer brothers, but Whittemore doesn't intend on sticking around for long.

As you have already heard, he takes matters into his own hands in the shape of a metal pipe, which he brings crashing down on Robert Holtman's skull.

A few days later, Holtman dies of his injuries, and a vicious young hoodlum becomes a full-fledged murderer.

Now, you'd think someone who just killed a man while escaping prison might choose to lay low for a while.

No, not Richard Whittemore.

First, he makes his way to Philadelphia, where he puts a new gang together.

Then, just three weeks after his escape, he brings the crew back to Baltimore to carry out a job.

All right, now, let's just think about this.

He could have picked a target in Philly, or anywhere, to be honest.

But no.

He deliberately goes back to Baltimore, where he knows the police are looking for him.

In fact, they're not just looking for Whittemore.

They've got orders to shoot on sight.

He's taking a huge risk.

Why?

The only possible explanation is, just for the hell of it, this guy's arrogance is breathtaking.

For this job, the gang targets a middle-aged bank messenger called J.

Wall Holtzman.

Whittemore has done his homework, finding out where Holtzman lives and what his daily routine is.

All that time listening to his mentors, the Cramers, has paid off.

Holtzman's job is to go to local businesses and pick up their cash to deposit at the bank.

Whittemore knows that when Holtzman leaves his home after his lunch break, he could be carrying as much as $10,000.

That's around $175,000 in today's money.

As Holtzman gets into his car, two masked men jump in, one in the back and one next to him.

The guy in front is Whittemore.

He laughs as he waves the gun in Holtzman's face, snarling, Do as I say or you'll be a dead guy.

Holtzman, he doesn't want to be a dead guy, so he does what he's told, which is to drive.

Whittemore directs him to a quiet back street about two miles away, where the rest of the gang is waiting with a stolen car.

They grab the two satchels of cash Holtzman is carrying and speed off.

The crime takes place in the middle of the day, another sign of Whittemore's recklessness.

Okay, yeah, he's got a scarf over his face, but he obviously gets a kick out of taking risks.

After the Holtzman ambush, the gang begins to feel the heat in Baltimore, so they move operations 200 miles northeast to New York.

It's a different state, which means a different criminal jurisdiction.

They can start again with a clean slate.

Then, in April 1925, the Cramer brothers finally make parole.

They head to New York to team up with Whittemore.

The Cramer's are the brains of the operation.

Whittemore is the brawn, a weapon they can use to get what they want.

And what they want is diamonds.

Under the Cramer's influence, the gang carry out a series of armed robberies, all meticulously planned and ruthlessly executed.

It starts in May 1925 with a raid on Ross's jewelry store on Grand Street, New York.

The gang carries out roughly one heist per month over the spring and summer of 1925.

Their operations cover a wide area with robberies in Cleveland and Buffalo, as well as New York.

Motor cars are becoming faster and more reliable, which helps them achieve their impressive range.

They have their own Cadillac, but always steal a fresh vehicle for each job, switching plates to confuse the police.

It's estimated that the total value of their takings over a five-month period is as much as $250,000.

When you take inflation into account, that's worth over $4 million today.

Who knew armed robbery could be so lucrative?

The gang members dressed like movie stars, or movie stars pretended to be gangsters.

They wear fashionable suits and coats and position their fedoras at an angle.

They project a glamorous outlaw image.

The public sees them as daring heroes, taking what they want so they can live the life everyone aspires to.

What about the victims?

Well, jewelry stores have insurance, don't they?

And somehow, nobody really thinks about the ordinary Joes who are terrorized while just doing their jobs.

Maybe that says a lot about the spirit of the age, brash, hedonistic, and a little heartless.

Truth is, the gang's exploits sell newspapers.

Even when they start killing people, the public laps it up.

The gang keeps their weapons in a locker at New York Penn Station.

If any of them are picked up with guns on them, they're in big trouble.

This is where Margaret comes in.

She's the gang's gun girl, taking the weapons out of the Penn Station locker and carrying them to a meeting point in a large bag.

Now, as a woman, she's far less likely to be stopped than any of the men.

In the beginning, the weapons that Margaret distributes are used mostly as a threat.

A way of getting store owners to hand over the goods.

Once or twice, Whittemore has to resort to pistol weapon some would-be hero.

Just to show he means business.

No one's been killed yet.

All that's about to change.

In the fall of 1925, the gang decides to branch out from jewelry theft and go after hard cash in Buffalo.

It's a decision that has fatal consequences.

It's 9:15 a.m.

on Thursday, October the 29th.

An armored Federal Reserve truck pulls up outside a branch of the Bank of Buffalo.

Fifteen minutes later, the bank opens its front doors and an employee comes out.

The Federal Reserve Guard, riding shotgun, gets out of the truck and walks around to the rear.

He opens the doors and takes out two bags of cash.

As the guard hands over the bags to the bank clerk, a fashionably dressed young man, wearing a fedora, strolls up and pulls a revolver.

Stick them up, he shouts.

Yeah, it's cliché.

The thing is, it generally gets results, but not this time.

This time, the clerk doesn't stick them up.

Unfortunately for him, the man with the gun has a short fuse.

Yeah, that's right.

It's Whittemore.

Whittemore pulls the trigger and shoots the clerk in the arm.

The clerk drops the bags.

Whittemore scoops him up and runs off.

A Buick appears from nowhere, speeding the wrong way up a one-way street.

It's the rest of the gang.

Some of the men in the car get out and open fire.

Others empty their guns from inside.

All hell breaks loose.

There's a shootout on the street, with pedestrians caught in the crossfire.

The Federal Reserve driver takes a bullet in the side of the head and dies instantly.

Sheltering behind the truck, the guard takes aim at Whittemore and fires.

Whittemore drops one of the bags he's carrying.

There's a stinging pain in his wrist.

He looks down and sees blood, but carries on running towards the Buick.

A second later, the truck guard emerges from his hiding place to take aim again.

But one of the gangsters' bullets finds him first.

Crumples hits the ground.

The Buick tears away.

Whittemore and the other gang members jump onto the running boards as it gathers speed.

An on-duty cop races to the scene, firing his gun at the moving car.

He takes out a side window and one of the tires, but the car carries on moving.

The cop flags down a passing car and orders the terrified driver to follow that car.

But just then a street car pulls out, cutting off their pursuit.

The gangsters get away.

The whole incident takes less than a minute.

One man is dead.

Another will die later from his wounds.

But for Whittemore and his gang, it's the best minutes work they've ever done.

When they finally ditch the stolen Buick and count their takings, they discover $93,000 in the satchel.

That's over a million and a half dollars today.

And this is hard cash.

They don't have to fence it.

They just have to spend it.

To do that, they head back to New York City.

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Whittemore's own wound turns out to be superficial.

The bullet just nicked him.

It's a small price to pay for such a rich haul.

$93,000 will keep him in seal skin coats, fedora hats and sharp suits for quite a while.

Not to mention clothes and trinkets for their lady friends.

The gang has acquired expensive tastes.

They like to party, and for them, no party is complete without drugs.

Whittemore's own weakness is for cocaine.

His coke addiction is said to be one of the reasons for his candy kid moniker, candy being a street term for cocaine.

But candy could also refer to his other addiction, diamonds.

After the success of the Buffalo Federal Reserve hijack, the gang could be forgiven for living the high life for a while.

But Whittemore takes time out from partying to settle a couple of personal scores.

On Sunday, November the 1st, he travels to Baltimore to gun down a bootlegger called Spike Kenny, who he suspects of having an affair with Margaret.

After the attack, Kenny's overcoat is riddled with bullet holes.

But miraculously, he survives.

The guy shooting from the hip doesn't always guarantee the best name.

Back in New York, Whittemore settles the second of his scores.

This time, his name is more accurate.

The body of Cy Golden, a former friend and gang member who double-crossed Whittemore, is found dumped in a graveyard in Lower Manhattan.

Five bullets in his body.

His debt settled, Whittemore's gang carries out two more jewelry heists in December.

Then they receive a tip-off from a fence concerning a shipment of 100 uncut diamonds from Amsterdam.

The prize is too big to resist.

They begin planning what will be their richest heist to date.

It's also the crime that brings Candy Kid to the attention of his nemesis, Inspector John D.

Coughlin, and is the beginning of the end for the Whittemore Gang.

On the morning of January the 11th, 1926, Diamond importer Albert Goethevis and his brother-in-law, Emanuel Wehrmann, is ambushed by Whittemore and his gang as they're walking through New York's Diamond District in midtown Manhattan.

Inside Goethevis' overcoat pocket, there's a wallet containing 200 uncut diamonds that he's just withdrawn from the company's safe deposit box.

The haul could be worth anywhere between $100,000 and $500,000.

If the upper value is correct, that's over $8.5 million in today's money.

The Goethevis robbery is a daring and extremely violent ambush carried out in broad daylight in front of scores of witnesses.

Whittemore, in particular, shows no mercy to his victims, raining blows down on their heads with the butt of his gun.

What makes the crime even more audacious is that the streets of the Diamond District are generally crawling with police, whose job it is to protect the wealthy business owners from just this sort of attack.

Not surprisingly, the NYPD is embarrassed by the ease with which the robbers pulled off their vicious assault, and then there are all the other raids that have been happening over the last ten months or so.

The gang's high success rate hasn't gone unnoticed.

It's time to find out who's behind this violent crime wave and stop them.

This task falls to Inspector John D.

Coughlin.

Inspector Coughlin is a big, broad Irish-American with black bushy brows and a thick mustache.

He confronts the world with a piercing, uncompromising gaze.

Like Elliot Ness in Chicago, Coughlin has the reputation of being untouchable.

In other words, incorruptible.

Coughlin leads by example, inspiring fierce loyalty in his tightly-knit team of detectives.

Goldfish and Veermann survive the vicious assault, but they are not able to identify any of the attackers.

Inspector Coughlin is undeterred.

He reviews all the jewelry heists that have taken place in New York over the last year, looking for patterns.

He identifies several that share consistent features.

All take place in broad daylight.

All are meticulously planned and seamlessly executed.

All involve a fast car, recklessly driven, and the perpetrators are always sharply dressed in expensive clothes.

But the most striking feature of all these crimes is the violence.

At the same time as he is analyzing the heists, Inspector Coughlin receives information from the Cleveland Police about a gangster they are looking for called Joe Langdon.

The description of Langdon rings a bell with some of the Detectives and Coughlin's team.

Big ears sticking out of the side of his head like jug handles, small head, sickly complexion, and a shuffling walk.

They know him as Shuffles Goldberg.

Like many gangsters of the period, this guy uses a number of aliases.

Goldberg is also wanted by Baltimore Detectives, who suspect him of involvement in the attack of the bank messenger.

Remember, that was the incident that kicked off the gang's crime spree back in March 1925.

Now, Coughlin notices similarities between the two muggings.

It looks to him like the same gang.

A gang which counts Shuffles Goldberg as a member.

Inspector Coughlin tasks his most trusted detectives with finding Goldberg.

He has them do the rounds of New York hotels describing Shuffles Goldberg to the staff.

Pretty soon, they track him to the Empire Hotel on West 63rd Street.

The detectives are eager to bring him in, but Coughlin's instincts are to wait.

He's got a hunch Goldberg's going to lead him to the rest of the gang.

So he instructs his men to put a tail on him.

It's a good call.

The detectives stick close to Goldberg, taking turns following him, so he doesn't get suspicious.

He leads him to an upscale apartment building on the Upper West Side.

Sometime later, Goldberg emerges in the company of a good-looking couple dressed to the nines.

She's drippin with diamonds.

He's wearing a tailored suit and silk shirt.

Inquiries with the building's management reveals the identity of the couple as Mr.

and Mrs.

Horace Q.

Waters.

Coughlin's men follow Goldberg for several days.

His routine never varies.

He meets the Waters at their apartment, then goes to lunch with them at the hotel or store or some other high-end eatery, where they meet up with other fashionably dressed friends.

Among them, the Detectives notice a pair of slightly older men who could be brothers.

The day usually ends at Club Shante, one of New York's most celebrated nightspots.

There, in the words of one club employee, Mr.

Waters spends money like a millionaire.

The Detectives can't keep up with Horace Waters' spending, but they keep him in their sights.

Something about his face looks familiar.

Then, one night, the penny drops.

That's Dick Whittemore, one of the Detectives says.

Baltimore wants him.

If Mr.

Waters is Richard Whittemore, then Mrs.

Waters is likely to be Margaret.

Next, the Detectives identify the two older men as Leon and Jacob Kramer, known as Prolific Safecrackers, with a long criminal record.

The Detectives report back to Inspector Coughlin.

After a little digging, he discovers that the Kramers served time in Maryland State Penitentiary with Whittemore.

That must be where they teamed up.

He's pretty sure he's looking at the core members of a criminal gang.

And his hunch is, it's the gang that held up Albert Goedfuss and Emanuel Vierman.

The way they're throwing money around, it certainly looks like they hit the jackpot recently.

Coughlin bides his time, waiting for the right moment to make his move.

And that moment comes in the early hours of March the 19th, 1926.

That night, two of Coughlin's men, Detectives Sullivan and Cronin, follow Shuffles Goldberg de Clubbe Shante.

Whittemore, Margaret and the Cramer brothers are also there.

Whittemore is in a belligerent mood.

He shouts at the staff, complaining about the wine.

At one point, he pulls a gun on a waiter.

The manager tries to calm things down, but Whittemore is out of control.

It looks like the candy kid's been at the candy.

Sullivan and Cronin exchange a wary glance.

Maybe they should haul him in before he does something dangerous.

They decide to wait a little longer.

They watch as Whittemore bullishly announces he's got better wine at his apartment.

He's going to get a bottle, and he wants the manager and the waiter to go with him.

Don't ask me why.

I'm just in one of those moods, I guess.

The two guys can see he won't take no for an answer.

So they go along.

Outside the club, Whittemore and his new best buddies get into the gang's Cadillac and head off.

By now, it's around 5 a.m.

Whittemore's driving is all over the place, as he swerves wildly across the road.

He doesn't see the car with its lights off, tailing him a carefully judged distance.

Detectives Sullivan and Cronin follow Whittemore to the upper west side, where he disappears inside his apartment building to pick up a bottle of wine.

Then he drives to a restaurant on Broadway.

As Whittemore's party goes inside, the two detectives watch the restaurant from across the street.

Eventually, Whittemore and his two reluctant companions come out.

They get back in the car and drive off.

Just as the sun is coming up, maybe Whittemore is sobering up a little, because he looks in his mirror and sees a car on his tail.

It's the cops.

Has to be.

Whittemore puts his foot down.

The car behind accelerates to keep up.

At times the two cars are bumper to bumper.

Whittemore reaches out the window with a gun in his hand and starts shooting.

With half an eye on the road in front, Whittemore's aim is about as erratic as his driving.

Behind the wheel of the other car, Detective Sullivan does his best to avoid the bullets.

While Detective Cronin unholsters his gun and returns fire.

Before long, Whittemore is all out of ammunition.

At the same moment, the Cadillac runs out of gas and the detective's car pulls alongside, forcing him over the side of the road.

The two detectives get out, they run over the Cadillac, they point their guns at the men inside and shout for Whittemore to stick them up.

For once, he knows what it's like to be staring down a barrel of a gun.

Whittemore's got one last trick of his sleeve.

As the detectives disarm him, he holds out two $1,000 bills.

That's about half their annual salary for each of the cops.

But, just like their boss Coughlin, Detective Sullivan and Cronin are untouchable.

They snap on the handcuffs and take Whittemore in.

Despite the fact that it was New York detectives led by Inspector John D.

Coughlin who arrested him, Whittemore is taken to Baltimore to stand trial for the Federal Reserve truck heist in which two men died.

Several witnesses place him at the scene of the crime, but the jury fails to reach a decision and a mistrial is declared.

Whittemore then has to answer for the murder of prison guard Robert Holtman.

This time he is found guilty and sentenced to death.

Crowds of supporters gather outside the Maryland Penitentiary, the very prison where he killed Holtman.

The newspapers write sympathetic stories about the candy kid and the woman they are now calling Tiger Girl because of her fierce devotion to her husband.

The dime store thriller of two heartless gangsters has turned into a love story of the age.

Richard Reese Whittemore is hanged on Friday, August 13, 1926.

No one could claim he is an innocent man, but many see him as a tragic hero.

At his funeral, it is said that Margaret has to be prevented from throwing herself in the open grave.

Margaret Whittemore is never convicted for her part in any of the gang's crimes.

She later remarries and dies at the age of 90 in 1993.

Despite his success in bringing the candy kid to justice, Inspector Coughlin's career ends in disappointment.

In 1928, he is forced out of the Detective Division after his failure to solve the notorious gangland killing of Arnold Rothstein.

Not surprisingly, no one else was able to crack that case either.

Maybe that's a story for another day.

If you want to hear more stories of real detectives who worked extraordinary cases, search for and follow Detectives Don't Sleep, wherever you listen to podcasts.

American Criminal is hosted, edited, and executive produced by me, Jeremy Schwartz.

Sound design by Matthew Filler.

Music by Thrum.

This episode is written and researched by Terrell Wells, managing producer Emily Burke.

Executive producers are Joe Callan, William Simpson, and Lindsey Graham.

In 2008, a promising young actor showed up on his first day on set, ready to film the action-packed climax of his movie.

It was full of difficult wire work and stunts, but he was ready.

He'd been training.

Cameras rolled, and he tore his butt cheek.

That actor was Robert Pattinson, and the film was Twilight.

What Went Wrong is a podcast dedicated to the idea that every movie is a miracle.

Join me, Lizzie Bassett, and my co-host Chris Winterbauer every other week as we unearth the chaos and humanity behind Hollywood's biggest flops and most shocking successes.

We're not here to dunk on movies.

We're here to celebrate them.

As the New York Times said, we're movie industry people who truly love films and the people who make them.

Listen to What Went Wrong wherever you get your podcasts.