Leopold and Loeb | Cry for Blood | 4

It's the afternoon of May 29th, 1924.

At the opulent Hotel LaSalle in downtown Chicago, a pair of detectives lead Nathan Leopold into a suite.

19-year-old Nathan looks around the space, and his eyes go immediately to a man sitting at a table made of polished wood, Robert Crowe.

The state's attorney is 45.

He stands when he sees Nathan.

He's got a boyish face, and the way his hair swoops across his sloping forehead makes him look even younger.

His round glasses have thick lenses, and his shirt strains just a little at his stomach.

It's his mouth that hints that he's not a man to be messed with.

It rests in a frown, his jaw tight as he reaches out to shake Nathan's hand.

Crowe gestures to Nathan, who takes a seat at the table.

Nathan swallows.

He can't help feeling nervous.

It's been eight days since he and Richard Loeb abducted and killed Bobby Franks, and this is the second time he's been questioned about the case.

Still, he's not in handcuffs, and the cops who picked him up were in plain clothes, which he's taking as a good sign.

But when Crowe puts a pair of tortoiseshell reading glasses on the table between them, Nathan swallows.

Those are his glasses, and he knows they were found just a few feet from Bobby's body out near Wolf Lake.

Crowe asks if they look familiar, and Babe confirms that they look exactly like a pair he owns.

If he didn't know any better, he'd say they were his.

But his glasses are at home this very minute.

He's sure of it.

Crowe sits back in his chair and folds his arms.

His thin line of a mouth twitches up into a grim smile.

If Nathan's glasses are at home, he says, then that clears everything up right now.

He calls the detectives into the room and asks them to escort Nathan back home.

Nathan feels himself relaxed.

It's over, he thinks, but Crowe's not done.

He tells the cops to help Nathan find his glasses and then come right back here with them.

Nathan just cannot stop himself from asking, what if they can't find the glasses?

Crowe smiles again and Nathan knows that's all the answer he's going to get.

He takes one last look at the glasses sitting there on the table and he wishes he could snatch them up and just end this whole ordeal.

But instead, he stands and buttons his coat.

He turns to follow the detectives back the way they came, trying to appear calm.

But he can feel sweat beading at his hairline.

He's certainly smart enough to think of a way out of this.

Something will come to him soon.

It has to.

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

In 1924, Nathan Leopold and Richard Loeb set out to commit the perfect crime.

They wanted to kidnap a child and collect a $10,000 ransom from his parents.

But for that to be the perfect crime, a murder without consequences, they need to not get caught, and that meant killing the only one who could identify them, their victim.

So that's what they did.

They grabbed 14-year-old Bobby Franks off the street, killed him, and hid his body in a drainage culvert.

But that was where the carefully planned out crime went off the rails.

It turned out that Nathan and Richard, for as smart as they were, had left plenty of clues for investigators.

And when they were cornered, these wannabe criminal geniuses couldn't stop themselves from spilling everything.

Once Chicago found out who was responsible for the brutal murder, the city saw red.

In a town run by violent thugs like Al Capone, this crime was a shocking new level of depravity.

And the fact that it was committed by two wealthy college kids just looking to get their kicks made it that much worse.

Everyone was ready to see the teens hang as soon as possible.

All of a sudden, it seemed like the only consequence free death Nathan and Richard had orchestrated was their own.

This is the final episode in our four-part series on Leopold and Loeb, Cry for Blood.

It's May 29th, 1924, less than an hour after state's attorney Robert Crowe sent Nathan Leopold home to look for his reading glasses.

At his family's Kenwood mansion, Nathan trudges up the main staircase towards his bedroom.

Two detectives are a few steps behind him, but it feels like they're breathing right down his collar.

When he opens his bedroom door, Nathan still hasn't thought of a way to get out of this.

Despite what he said, those glasses Crowe showed him at the hotel are his.

There's no way he can magically produce another pair to bring back with him.

Still, he's not going to admit that.

So while the detectives stand watching, Nathan makes a show of searching his desk, his nightstand and his closet.

He goes through each of the pockets in his many suits.

They've just got to.

Eventually, though, it's very clear that there are no reading glasses anywhere in Nathan's room.

So he asks his older brother Michael to help search the house.

Then the family's servants get involved.

Obviously, this does nothing except waste everyone's time.

When the mansion's basically turned inside out, Michael says what they're all thinking.

Maybe those glasses are Nathan's after all.

But then he says something helpful.

Nathan must have just dropped them the last time he was out birding at the lake.

Nathan can't agree with his big brother fast enough.

Yes, that's it.

He just dropped them when he was there a couple of weeks ago.

He'd already come up with that exact story to explain his glasses turning up near a murder victim, but he really hoped he wouldn't be forced to use it.

Now, he figures it sounds even more plausible because it was suggested by someone else.

He just hopes the state's attorney buys it.

Back at the Hotel LaSalle, Robert Crowe's not buying anything.

His questions get more and more pointed, but Nathan plays it cool.

He says that he remembers stumbling on a recent trip to the lake when he was trying to get closer to some rare birds.

The glasses must have fallen out of his inside breast pocket.

As far as explanations go, it's not bad, but Crowe's clearly not convinced.

He hands the spectacles to Nathan and asks him to recreate the moment.

Nathan stands up, tucks the glasses into his pocket and pretends to fall.

The glasses stay put.

Even when Nathan tries again and again, they don't budge.

Suddenly, his great story seems a lot less plausible.

After that, Crowe and his colleagues continue with their questions, pressing Nathan to account for his whereabouts on the day of Bobby's murder.

At first, Nathan seems to struggle to remember, but slowly he offers more and more details of the alibi he and Richard concocted.

They spent the afternoon driving around in his Red Willys night, having lunch, drinking and then looking for a pair of girls to have sex with.

While Nathan's telling his story to the state's attorney, the detectives head back to the Leopold house to look around.

Ostensibly, they're just picking up Nathan's typewriter to compare it against the ransom note, but they give his room a good go over too.

They grab samples of his handwriting, train timetables, and a letter Nathan wrote to Richard that referred to them both as, quote, cocksuckers.

Downtown, Nathan patiently answers questions about his alibi, about his studies, about how closely he's followed the Bobby Franks case in the papers.

He's even asked whether or not he's a quote unquote pervert, followed by some pointed questions about his relationship with Richard Loeb.

Nathan denies the accusations that he's gay, but that letter he wrote certainly makes things look abnormal for the 1920s.

Of course, the authorities aren't content to just take Nathan's word for it, so they pick up Richard.

They don't suspect him of anything just yet, but it's clear the two guys are close.

So if Nathan had anything to do with the murder, and if he told anyone about it, it would be Dickey.

So they bring up the letter when they're talking to him.

It's like they're hoping if they hint about exposing the guys just right, they'll scare him into ratting out Nathan.

And while Richard doesn't get rattled and he mostly stays on script, his version of the alibi for the murder is different enough from Nathan's that the cops decide they want to search his house too.

When Dickey arrives back in Kenwood escorted by police officers, there are journalists already waiting to get the story firsthand.

Some eager detective in the Chicago PD has already tipped them off.

From there, news that the teenage sons of wealthy families are being questioned about the murder ripples across the city.

During breaks and questioning, reporters are allowed to speak to the guys, who explain that they had nothing to do with Bobby Frank's death.

On the whole, they seem to find the situation pretty amusing.

In fact, they are gratified that people are paying attention to them.

And thanks to the symbiotic relationship between the media and the police in Chicago, they are getting plenty of it.

By this stage, Dickey and Babe have been in custody for over a day, and their families haven't made any attempts to intervene.

Neither of the boys are under arrest, so a lawyer should have no trouble extracting them from the criminal court building where they've been moved to.

But both their fathers are so convinced of their innocence that they're happy to let their sons help with the investigation in any way they can.

Of course, with all the interest in the murder case, that is all the newspapers it's selling every day, Chicago's editors are eager to get a scoop that will put them ahead of their competitors.

Two reporters from the Daily News decide to look into the ransom note angle and speak to members of Nathan's study group to collect copies of typewritten notes he's made.

One set of note looks different to the others and a student explains that they were studying in a different room in the Leopold house that week.

So Nathan was using a portable underwood typewriter, as opposed to his regular hammond that stays upstairs.

On the surface, that sounds innocuous enough, but experts have agreed that the ransom note delivered to Jacob Franks was likely typed on an underwood.

And comparing the study notes to the ransom letter proves they almost certainly came from the same machine.

The T, the I and the M keys all showed distinctive, identical abnormalities across the two documents.

Excited that they've got their scoop, the Daily News journalists share what they found with the authorities who confront Nathan.

As usual, he bats their questions back, saying that the typewriter he used for the study notes was owned by another student.

Even still, the cops head back to the Leopold house with Nathan to look for the underwood, which Babe and Dicky destroyed a week ago.

A maid admits that there was an underwood in the downstairs library for a while, but that it disappeared recently.

A clearly annoyed Nathan tells the maid that she's mistaken, but the bell's been rung.

Now, if the cops can find that typewriter, they will have physical evidence tying Nathan to the crime.

The glasses are a solid clue, but they can be explained away by a story about bird watching at the lake.

So they invest time speaking with other members of the study group to ask them what they know.

While all this is going on, Nathan's family are waiting calmly at home for the authorities to do their job and clear them of any wrongdoing.

They trust the police will figure out that Babe and his friend have done nothing wrong.

And when their chauffeur comes to tell them what he knows about the day of the murder, they're certain they've got the proof the police need.

Sven Englund explains to Nathan Leopold Sr.

that he saw Nathan and Richard together on the afternoon of the murder.

Babe even left Sven his car so he could fix the brakes, so he couldn't have been driving around the countryside dumping a body.

It seems like a perfect alibi, so Nathan Sr.

asks Sven to speak to the authorities right away.

Except no one outside of the investigation knows about the story Nathan and Richard have been telling.

You know, the one where they spent all afternoon driving around in his red car, eating, drinking, picking up dames.

So when Sven goes to the state's attorney to tell him that Nathan's innocent because he didn't have the car that day, he confirms that Babe and Dickey have been lying the whole time.

In short, it's a disaster for Nathan and Richard.

For state's attorney Robert Crowe though, it's exactly what he's been waiting for.

Once Sven leaves, Crowe heads to the interrogation room holding Richard and confronts him with the lie.

For a while, Dickey treads water, claiming that the chauffeur must be mistaken.

But when he hears that Sven has told them that he had Nathan's car all day, the blood drains from his face and he whispers two words, my God.

After that, he starts to confess.

Actually, first he asks for a lawyer, which is a request that Robert Crowe ignores.

Then Dickey starts talking.

And criminal mastermind that he is, he does everything he can to foist most of the blame on Nathan.

It's around the time that Richard's confessing that a message comes for Crowe.

Nathan's got a question.

He wants to know, hypothetically speaking, if a well-connected, wealthy young man was accused of murder, what his chances of beating the rap would be.

At this point, Crowe can smell victory.

He leaves Dickey and heads to Nathan's interrogation room, where Babe coolly tells him that he'll never charge him with murder.

He doesn't have the goal.

That's when Crowe tells him that Richard's been busy confessing on the other side of the building.

They know all about the ransom plot, the rental car, everything.

That knocks the smirk right off Nathan's face.

And when he hears that Dickey's trying to pin the whole idea on him, he panics and starts to give his version of events.

It's just after 6 a.m.

on May 31st, 10 days after the murder, and Robert Crowe emerges from his office to speak to the press.

Reporters have been gathered in the halls all through the night, and now they wait to hear what the state's attorney has to say.

Crowe looks tired but elated.

With a grim smile, he announces that the case that shocked Chicago has been solved.

Leopold and Loeb, he says, have confessed at last.

Imagine fast hydration, combined with balanced energy, perfectly flavored with zero artificial sweeteners.

Introducing Liquid IV's new energy multiplier sugar-free.

Unlike other energy drinks, you know, the ones that make you feel like you're glitching, it's made with natural caffeine and electrolytes, so you get the boost without the burnout.

Liquid IV's new energy multiplier sugar-free hydrating energy.

Tap the banner to learn more.

This episode is brought to you by LifeLock.

When you visit the doctor, you probably hand over your insurance, your ID and contact details.

It's just one of the many places that has your personal info.

And if any of them accidentally expose it, you could be at risk for identity theft.

LifeLock monitors millions of data points a second.

If you become a victim, they'll fix it, guaranteed, or your money back.

Save up to 40% your first year at lifelock.com/podcast.

Terms apply.

It's the morning of June 1st, 1924 in Jackson Park, Chicago.

Just over 24 hours ago, Nathan Leopold and Richard Loeb confessed to killing Bobby Franks in cold blood.

In that short time, Leopold and Loeb have already become household names around the country.

Profiles of the killers have filled countless inches in newspapers, with plenty more delving into the details of their confessions.

The stories even made the front page of the New York Times.

Now police officers are escorting Nathan and Richard around Chicago on a grand tour of their crime.

The guys have been asked to help investigators collect the evidence that will prove the case against them.

And Babe and Dickie seem happy to share every intricacy of their brilliant plan.

But they're not doing it alone.

A number of reporters have been invited to join the procession through the city.

Some of them even riding in the cars with the killers.

Their first stop this morning is the bridge in Jackson Park, where Richard threw the keys from the Underwood typewriter into North Pond.

When the car he's in pulls over, Dickie reaches for the door handle, but one of the reporters stops him.

He points to the edge of the water, where a large crowd of people are watching the divers searching.

The journalists suggest Richard might want to stay put to avoid all that attention.

Richard doesn't respond for a sec.

He stares at the onlookers a couple of hundred feet away, then shakes himself free of the reporter's hand and opens the door.

He's not scared for people to see him.

He says he's not scared of anything.

The number of people who turn out to watch the cops search the pond for the typewriter keys is hardly surprising.

Local papers are already calling the murder of Bobby Franks the worst crime Chicago has ever seen.

And in a place where gangland crime is a daily occurrence, that's a big call to make.

But it feels true.

Mob hits her old hat.

But this?

This kind of scheming, calculated, cold-blooded murder of a child for fun?

That's a new low, and it's made Chicago bloodthirsty.

Newspapers publish pieces demanding a rapid trial and a swift execution so as to preserve the city's moral standing.

The Evening American even cites the Old Testament when making their case that the killer should swing.

And it seems likely that everyone's gonna get what they want.

With their confessions on record, the case against Babe and Dickie seem completely ironclad.

There's no possible way they'll walk away from this.

Everyone knows that.

But the killer's families aren't willing to watch them die.

So, while their sons are helping the cops find the evidence that could get them hanged, Nathan and Richard's relatives pay a visit to the one man they think might be able to help them.

By the time Nathan and Richard's families seek him out, 67-year-old Clarence Darrow's reputation is as the best trial attorney in Chicago.

And probably the country.

For over three decades, he's represented corporations, cities, labor unions, and killers.

He's a gifted speaker, and his closing arguments are the stuff of legend.

They even get printed in the papers.

When Darrow speaks, everyone listens.

Plus, he's already on good terms with the Loebs, so he hears the families out when they beg him to represent Babe and Dickie.

They'll pay him anything he wants.

No one's under any illusion that they can possibly get a not guilty verdict.

For starters, there's the confessions.

And what's more, no one wants Nathan and Richard to walk free, not even their families.

But that doesn't mean their parents, brothers, uncles, aunts, doesn't mean they want them to hang.

So all Darrow is being asked to do is make sure they don't get the death penalty.

Easy, right?

Luckily for the Leopold and Loeb families, Clarence Darrow is a staunch opponent of capital punishment.

That's why he agrees to take the case.

Sure, he's friendly with the Loebs, and yeah, he'll probably make some nice coin off the case, but he mostly wants to push back against the whole concept of the death penalty.

So just when it feels like the case couldn't possibly get any bigger, the most famous lawyer in the country jumps into the fray.

But while Darrow can't stand the idea of the government killing people for their crimes, state's attorney Robert Crowe is a big fan.

Back when he was a judge, he made a name for himself by sending a killer to the gallows despite the man pleading guilty, an act that usually merits some leniency and punishment.

Now he's determined that his prey won't escape him in this case either.

Even before Nathan and Richard's families formally launched their defense, he's anticipating ways to counter it.

The newspapers have already moved on from analyzing the confessions to theorizing about the motive.

The most popular idea, the one that's easiest to understand, is insanity.

What else could inspire intelligent young men from wealthy, well-respected families to kill?

They must be crazy.

So Crow wants to prove that the killers are completely sane.

For an insanity defense to be effective in 1924, a defendant needs to prove one of two things, that they don't have the power to distinguish between right and wrong when it comes to the crime in question, or that they were incapable of making a choice about actions that they knew were wrong.

With that in mind, Crow brings in respected psychologists to examine the defendants and give their opinion.

To a man, they all say that Nathan Leopold and Richard Loeb are not insane.

That's good enough for Crow, who's feeling more confident by the day.

These boys will swing before the year is out.

On June 11th, three weeks since the crime, hundreds of people line up outside the Cook County Courthouse.

All of them desperate to get inside to hear how the confessed killers plead to the charges.

Since everyone's read all about Nathan and Richard in the papers, there's no mystery left to the crime.

But how they plead will hint at what their legal strategy at the full trial might be.

When the courtroom is open to the public just before 10 o'clock, the surge to get inside is so massive that one of the oak doors is pulled from its hinges.

People sit on every seat, stand where there are no benches left, then squeeze onto the window sills.

All of them fall completely silent when the accused enter the room.

They hold their breaths until Nathan and Richard plead not guilty to charges of kidnapping and murder.

With that out of the way, Judge John Caverly schedules the trial to begin in early August.

That gives both sides a little under two months to prepare.

But all the time in the world won't help Clarence Darrow achieve the impossible.

There's too much stacked against them for any jury to find them innocent.

And a guilty verdict will surely mean a death sentence.

The entire city is screaming for blood.

But there's one thing they could try that just might work.

Or it'll earn them an even earlier date with the Gallows.

On July 21st, exactly two months after the murder, Judge John Caverly's courtroom is full of people again.

This time to hear pretrial motions.

Darrow's got a doozy.

He stands and asks that the defendants be allowed to enter new pleas of guilty.

Those few words send a ripple of shock across the courtroom.

With guilty pleas on the record, the case will bypass a jury and go right to the sentencing phase.

That means it'll be up to the judge to decide on a punishment.

But Darrow goes on to explain that he would like the chance to demonstrate mitigating factors during the sentencing period.

These mitigating factors will include the mental state of the defendants.

Robert Crowe is livid when he hears this.

He spent months working on the case, on ensuring there's no way for Nathan and Richard to escape their fate.

And now, Darrow's trying to cheat him?

He tells Caverly that the defense is attempting to avoid a jury trial while still putting on a full insanity defense.

Either the defendants are guilty as they have just stated or they're not, he says.

They can't be guilty and mentally deficient.

In 1924, that's not legally possible.

Despite Crowe's argument, Caverly allows the new pleas to stand.

They'll skip the highly anticipated trial and move directly to sentencing.

So if you ever hear people call this the first ever trial of the century, don't be smug, but you're allowed to correct them.

It's actually just a sentencing hearing.

But whatever you call it, it's a big shift for the two young men who began the year certain they could pull off the perfect crime without detection.

Now they're just hoping they'll live to see their next birthdays.

The hearing begins a couple of days later with arguments from the prosecution.

And Crowe wants to demonstrate just how much he could have proven the defendant's guilt if he'd been allowed to proceed with the full trial.

He calls over 80 witnesses who testified to just how awful the murder was, how thoughtfully Nathan and Richard planned it out, and how much it's affected Bobby's family.

The thrust of the argument is this, give Leopold and Loeb the noose.

It's better than they deserve.

Once the prosecution rests, Darrow and his co-counsel get ready to present their case.

Of course, the goal isn't to convince anyone that Babe and Dickey are innocent.

Instead, they've lined up a parade of witnesses who will testify to things that explain or rationalize the crime, or else make it seem less awful.

It's a tall order, one not made any easier by Robert Crowe.

The first witness for the defense, a physician, has barely sat down in the witness stand before Crowe jumps to his feet to object.

He says that if the defense tries to introduce any testimony about the boy's mental health, then Judge Kaverly must call for a jury to be seated and a trial begin.

It's the law, he insists.

The judge disagrees.

He says that he's just sat through the prosecution's lengthy arguments about why the boys should be killed, so now he needs to listen to arguments about why they should be spared.

It's only fair.

And in addition to being fair, Kaverly's decision to allow psychiatric testimony as a mitigating defense to murder will set legal precedent.

The first time it's happened in the criminal justice system.

Just another dubious notch in the belt for the Leopold and Loeb case.

Each of the psychologists to take the stand for the defense comes to a similar conclusion.

Nathan and Richard are emotionally stunted, mentally impaired young men with disordered personalities.

Neither display any remorse for their actions and instead seem more preoccupied with how the world sees them.

Not because they're concerned people will think they're monsters, but that they won't see their true brilliance.

When both sides are done with witnesses, it's time for closing statements.

And everyone is excited to hear Clarence Darrow speak.

Like I said earlier, his closings are legendary.

And he's hinted that this might be the last case he ever tries.

So, the afternoon he's scheduled to speak, some 2,000 people show up to try and get into the courtroom.

And the lucky hundred or so spectators who do make it inside are treated to an eight-hour marathon.

In a career full of incredible speeches, this one will be remembered by many as his very best.

Towards the end of his closing, Darrow subtly equates the brutal crime at the center of the case with the decision about whether or not to execute the killers.

The murder of Bobby Franks was planned, cold-blooded and remorseless, no question about it.

But Darrow presents Judge Caverly with another reality.

He says, quote, Your honor, if these boys hang, you must do it.

It must be your deliberate, cool, premeditated act without a chance to shift responsibility.

By the time Darrow's done speaking, the judge is in tears.

Not just for Bobby Franks, but for the boys' family and the families of Nathan and Richard.

And perhaps, perhaps even for himself.

Because Clarence Darrow is right.

Caverly knows that there's only one person left in this story who can make a decision about who lives and who dies.

And it's him.

This episode is brought to you by cars.com.

On cars.com, you can shop over 2 million cars.

That means over 2 million new car possibilities, like making space for your growing family, becoming the type of person who takes spontaneous weekend camping trips, or upgrading your commute.

Wherever life takes you next, or whoever you're looking to be, there's a car for that on cars.com.

Visit cars.com to discover your next possibility.

When did making plans get this complicated?

It's time to streamline with WhatsApp, the secure messaging app that brings the whole group together.

Use polls to settle dinner plans, send event invites and pin messages so no one forgets mom's 60th, and never miss a meme or milestone, all protected with end-to-end encryption.

It's time for WhatsApp.

Message privately with everyone.

Learn more at whatsapp.com.

It's September 10th, 1924.

It's been almost four months since the murder of Bobby Franks, and today, all of Chicago is eagerly awaiting the conclusion of the saga.

And I mean all of Chicago.

Inside Judge Caverly's courtroom, hundreds of people are packed into the gallery.

Journalists have squeezed themselves into the jury box, which hasn't been needed during the sentencing hearing.

Outside, some 200 members of Chicago's police force have been marshaled to stand guard at the building's entrance and all around the block.

All other cases have been moved from the schedule for the day to limit the number of people coming and going from the courthouse.

So yeah, it's tense when Judge John Caverly walks into the courtroom at 9.30 on the dot.

He orders that the crowd be seated and the defendants brought in.

After giving the press a moment to take photos, he demands silence and begins to read his decision.

While Nathan and Richard stare at fixed points in the room, Caverly explains that the psychological testimony offered during the hearing was fascinating and important for the field of criminology.

But ultimately, it had no impact on his decision.

Despite the defense's best efforts, there are no mitigating circumstances here, he says.

At that point, people throughout the gallery exchange looks, some of them whispering that those words are as good as a death sentence.

But then, Caverly swerves.

He announces that although it would be the path of least resistance to impose the harshest penalty here, that's not the path he's chosen.

If Nathan and Richard were older, he might have made a different choice.

But because they're not 21, not get legal adults, the judge can't see his way to executing them.

It wouldn't be right no matter what they did.

Anticipating that people will call him weak for his decision, Caverly points to illegal precedent.

In the history of the Illinois justice system, only two minors have ever been put to death, and he doesn't want to add two more names to that short list.

So instead, he sentences Nathan and Richard to life sentences for murder and an extra 99 years for the kidnapping charge.

Leopold and Loeb will live the rest of their days behind bars.

At least, that's the plan.

As news of the sentence ripples across Chicago, people start throwing around phrases like absolute travesty and miscarriage of justice.

Everyone seems to think that it wasn't their age, but their wealth that saved them from the gallows.

Surely, anyone in the same position without the same resources would have swung.

It's a compelling argument that justice system does seem to favor those with the means to pay for better representation.

But it might not be as straightforward as it seems.

The fact of the matter is that there were a number of factors at play during the sentencing.

One of them was the simple fact that they pled guilty to the charges.

Up until this point in the 20th century, only one man has entered a guilty plea and still been sentenced to death.

And the judge who sentenced him?

Robert Crowe.

So although a guilty plea didn't guarantee Babe and Dickie lenience, it definitely went a long way.

And despite what the rest of the city might think, it's a result that satisfies Bobby's parents, Jacob and Flora Franks.

Jacob tells the press that neither of them and one of their sons killers executed.

There's been enough death and heartbreak already.

Not that you'd know that by looking at Nathan and Richard.

The 19-year-old celebrate their sentence by ordering steak dinners from their cells.

All throughout the hearing, they've been fed by a local restaurant paid for by their families.

And they want one last hurrah.

The next day, they adopt their new identities as lifers.

Nathan and Richard's early years in prison are mostly unremarkable.

They're housed in separate facilities for a while, but are eventually reunited at the Statesville facility, about 35 miles outside of Chicago.

By this stage, it's been almost eight years since they murdered Bobby Franks together, and they both matured at least a little.

And because they're staring down many more decades locked up, they decide to make the most of it.

In late 1932, Richard suggests they work together to improve the educational facilities at Stateville, which currently only offers classes up to eighth grade.

They pitch the idea of a correspondent school to the warden and spend the next several years running the program and teaching their fellow inmates.

But all that comes to an end in 1936.

On January 28th, Richard Loeb is attacked by an inmate, James Day, wielding a straight razor.

James will tell different versions of the story after the fact.

He'll say that Dickey made unwanted sexual advances, or that he was trying to recruit him for a jailbreak.

The prison's chaplain will report that James attacked Richard for rejecting James' sexual advances.

In all versions of James' story, he and Richard struggle over the razor, which makes it sound like he acted out of self-defense.

But James will emerge from the encounter with no visible injuries, while Richard has nearly 60 separate wounds from the blade.

The worst is a deep slash across his throat, which looks like it came from someone standing behind him.

Richard is rushed to the prison hospital, and Nathan follows when he hears what's happened.

He sits at the foot of Dickey's bed while surgeons operate, but there's no saving Richard Loeb.

He dies at age 30, leaving his partner in crime to face the rest of his sentence alone.

It's April 1949, when everything changes again.

That's when Nathan's 99-year sentence for kidnapping is reduced to 85.

The reduction is in recognition of his contribution to a malaria study.

He had allowed himself to be infected with the disease and then be subjected to potential cures.

Now 14 years might not sound like a lot against 99 years, especially not when he's also serving the life sentence.

But here's the kicker.

Back in 1924, Judge Caverly neglected to specify that the two sentences be served consecutively.

So Nathan's been serving them concurrently by default.

And now that his sentence is that much shorter, he'll be eligible for parole in 1953, when he'll have served a third of his term.

His first application for parole is rejected, but in 1957, the Parole Board gives him the green light.

So in March 1958, after nearly 34 years behind bars, Nathan Leopold walks free.

He heads straight to Puerto Rico, where he's already secured a position as an X-ray technician at a church-run hospital.

He claims to be a reformed man with no interest in breaking the law and risking being returned to prison.

But even after everything he's been through, he's just as arrogant as ever.

He writes to old friends, telling them that he ignores his curfews, owns firearms, drinks alcohol and goes to bars.

All things he's forbidden from doing.

Rules have always been for other people, not for Nathan Leopold.

Eventually, he goes back to college to get his masters, secures a job teaching at a university, publishes a book about Puerto Rican birds, and even gets married.

For all intents and purposes, he lives a full life for 13 years, almost as long as the life Bobby Franks lived before Nathan and Richard ended it.

Then in 1971, 66 year old Nathan dies of a heart attack, but his legacy, his infamy will linger.

In the years leading up to his parole, Nathan Leopold wrote and published his autobiography, Life Plus 99 Years.

It sold a decent number of copies, but it was clearly a ploy to rehabilitate his image for the parole board.

He wrote charitably about himself and his crime, probably hoping that time would soften the horror and leave his words as the best to count around.

But he wasn't the only one to write a book about the murder of Bobby Franks and the killers who had fascinated America at the height of the Jazz Age.

Two years before Nathan's Autobiography, Meyer Levin published a novel about the case called Compulsion.

The book was a massive success, selling over a hundred thousand copies and hardcover than a million more in paperback.

Compulsion set a new standard for crime writing because it's considered by many to be the first ever example of a non-fiction novel, which is a form best utilized in true crime.

In the decade since its publication, iconic books like In Cold Blood, The Killer Beside Me and Killers of the Flower Moon have followed in its footsteps.

Aside from Compulsion and its film adaptation, there have been plenty more works inspired by one of the 20th century's first crimes of the century.

In 1929, a play called Rope hit the stage.

In it, two arrogant friends strangle a man to death, hide him in a trunk, then stage a dinner party on top of it.

Then, in 1948, Alfred Hitchcock adapted the play into a film.

There have been musicals, TV episodes, stacks of books and even a graphic novel, all centered around or inspired by this story.

Each in their own ways, artists, biographers, criminologists and historians have grappled with the story of Leopold and Loeb, with the two young men at its center, with their relationship and the crime they committed.

Was one of them more to blame than the other?

Would either of them have become a killer on his own?

Did they actually want to get caught?

How much were their governesses to blame?

What about their fathers?

People commenting on the trial at the time said it was too much jazz that did it, or an excess of booze, a lack of religion, too much freedom, too few restrictions.

No one could agree on the root cause, an explanation for what happened.

And a hundred years later, we're still searching.

Who knows, maybe today's psychologists would be better equipped to offer a diagnosis for the two killers, though that really does just seem like cold comfort.

Because when you look at them side by side, a lot of crime stories can be boiled down to a fairly simple explanation.

We're talking basic driving concepts like sex, money, power, fear, jealousy.

But it's so much harder to do that here.

Nathan Leopold and Richard Loeb didn't kill because they wanted anything.

They didn't commit crimes because they were driven by a deep-seated compulsion.

They did it because they thought it would be interesting.

They were curious.

They were bored.

And they were both smart enough and dumb enough to think they could get away with it.

And afterward, they felt nothing.

They hoped for a level of respect or acclaim, acknowledgement of their superior intellects and criminal genius.

What they got was infamy.

From Airship, this is the final episode in our series on Leopold and Loeb.

On the next series, a twisted collection of Halloween-inspired crimes because of all the things that go bump in the night.

The scariest are humans.

We use many different sources while preparing this episode.

A few we can recommend are Leopold and Loeb, The Crime of the Century by Hal Higdon, The Leopold and Loeb Files by Nina Barrett, and For the Thrill of It by Simon Bottz.

This episode may contain reenactments or dramatized details, and while in some cases we can't know exactly what happened, all our dramatizations are based on historical research.

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

Audio editing by Mohammed Shazi.

Sound design by Matthew Filler.

Music by Throm.

This episode is written and researched by Joel Callan, managing producer Emily Burke.

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