- [Narrator] Coming up.

- The story of Leopold and Loeb is the story of the original crime of the century.

- [Narrator] A hundred years ago, the senseless murder of 14-year-old Bobby Franks transfixed the city of Chicago, and the nation.

- It was horrible.

They killed him ruthlessly.

- [Narrator] Just as shocking was who committed the crime.

Nathan Leopold and Richard Loeb, teenagers from extreme wealth who forged a dark pact.

- These two privileged boys killed another boy from within their community, and we have no reasonable explanation for it.

- They just enjoyed the thrill of killing.

- They're gonna create the perfect crime.

It's fun for them.

- [Narrator] Some call it the murder that wouldn't die.

- People love to speculate.

What was the actual motive?

Why did they do this?

How did they get to this point?

- They both blamed one another.

Who was lying?

Who wasn't lying?

That's another part of the mystery.

(dramatic music) - [Narrator] Deadly Alliance: Leopold and Loeb Next on "Chicago Stories."

(dramatic music) On a Wednesday afternoon in May 1924, 14-year-old Bobby Franks left the prestigious Harvard School for Boys in Chicago's Kenwood neighborhood, and headed south along Ellis Avenue, like he did nearly every weekday.

But on this day, he never made it home.

(ominous music) - It was a little late for Bobby.

He'd actually stayed after school so that he could umpire a baseball game that his friends were playing in.

- (Nina) At some point, he walked away from the game to walk the three blocks home, and then he disappeared.

(ominous music) - [Narrator] Bobby's parents, Jacob and Flora Franks, were expecting him by supper.

- And at first his parents weren't that worried because it was a very safe neighborhood.

- [Narrator] Kenwood, on Chicago's south side, was an insular haven where the boulevards were lined with mansions.

Owned, in large part, by elite Jewish businessmen.

- The Kenwood neighborhood was very rich.

The houses were stately, they were big.

People had servants.

They had chauffeurs.

(gentle music) - [Narrator] It was a world away from the Prohibition Era crime and gangland violence that plagued other parts of the city.

- There were many prominent people living there at that time, which is what made the disappearance of Bobby Franks so shocking.

(gentle music) - [Narrator] Jacob Franks was the former owner and president of the Rockford Watch Company and had vast real estate holdings, including his grand Kenwood mansion.

(gentle music) He and wife Flora, 20 years his junior, were parents to three children: Josephine, Jack, and Bobby.

- (Nina) Bobby was the youngest.

He was 14.

So he was on the verge of adulthood.

If you were a young guy, you wore these sort of short pantaloon-like pants and these knee socks.

And they had just been talking about taking Bobby to buy his long pants.

(dramatic music) - [Narrator] As dinnertime came and went on this May day, Bobby still hadn't returned.

And a growing sense of unease settled over the Franks' home.

(dramatic music) - (Candace) Every time a car goes down the street, everybody sort of tenses.

Surely this is someone delivering Bobby safely home.

- (Erik) Jacob Franks and his friend started to search the neighborhood for him.

Flora Franks started to call Bobby's friends, and nothing.

(ominous music) - [Narrator] Jacob Franks continued to search while a family friend contacted police.

While they were out, a call came into the Franks' home.

(ominous music) (phone ringing) - (Paul) It's a male voice and it sounds slightly menacing, and this voice informs Flora Franks that her son Bobby has been kidnapped.

But he's safe.

And if they simply wait further instructions, there will be an opportunity to ransom him back.

Immediately upon hearing the fate of her son, Flora Franks faints.

She just drops the receiver and falls to the floor.

(ominous music) - They knew then that there was a kidnapping and that they were gonna have to wait for the next morning to get any further information.

So it must have been an absolutely horrible torturous night.

(ominous music) - [Narrator] The next morning, the postman arrived with an envelope addressed to Jacob Franks.

- He has a letter that was sent special delivery.

When he opens it up, he reads, "Dear Sir: As you no doubt know by this time, your son has been kidnapped."

- It was unbelievably literate, which indicated to them that it was written by someone educated.

- [Erik] "Allow us to assure you "that he is at present well and safe.

"You need fear no physical harm for him, "provided you live up carefully to the following instructions."

(dramatic music) - [Narrator] He should not contact the police or his son would be killed.

He should get $10,000 in old bills, place the cash in a cigar box, and await further instructions.

Then, a final word of warning.

- [Erik] "We are prepared to put our threat into execution.

"...should you carefully follow out our instructions "to the letter, we can assure you that your son "will be safely returned to you.

Yours truly, George Johnson."

- And Jacob Franks was going to do anything he could do to try to save his son.

And so he did in fact actually go to the bank and he got the money.

(ominous music) - That boy was, without a doubt, the light of his life.

He was intelligent, he was bright.

The whole family was all about Bobby.

He was their star.

(ominous music) - [Narrator] Unbeknownst to the Franks' family, 15 miles away, a tragic discovery was about to change their lives forever.

(dramatic music) On Thursday, a factory worker clocked out of his shift for the day and took a shortcut through the Wolf Lake Forest Preserve that straddles the Illinois and Indiana state line.

(dramatic music) - And while he's walking down that path, he notices in this culvert, in this ditch, he sees this body, and he doesn't quite know what to do.

(ominous music) - He flagged down a couple of railroad workers that were close.

And together, they pulled the body out of the pipe.

(ominous music) Saw that it was a young boy and summoned help.

(ominous music) - [Narrator] Police arrived to find that the deceased boy was nude, had a gash on his head, and brown-colored stains on his face and genitals.

(dramatic music) A search of the wooded area revealed little, save for a single sock and a pair of small tortoiseshell eyeglasses.

- The police who collected the body and took it to the morgue picked up the eyeglasses and put them on the boy's body because they assumed they belonged to the boy.

- [Narrator] But who was the boy?

No one knew.

Until later that day, when police got word that a millionaire's son was missing from Kenwood.

- So a phone call was placed to the Franks' household.

Jacob Franks took the call.

The police officer described for him what was found with the body.

(dramatic music) - [Narrator] Franks was told that the deceased boy was wearing glasses.

It came as a relief.

Bobby didn't wear glasses.

It couldn't be him.

Still, they sent the boy's uncle to the morgue to identify the body to be sure.

(dramatic music) - (Candace) And he does discover that that is Bobby Franks.

And so he calls home to let the rest of the family know that this is indeed Bobby's body.

(dramatic music) - [Narrator] Now, the glasses found at the scene became the key piece of physical evidence in a homicide case.

(dramatic music) - (Penny) The police thought that the glasses had to be tied to the murderers for the simple reason that they were found out at the lake near Bobby, but not in the brush.

They were lying on top of the grass.

They were clean.

They hadn't been there for very long.

(ominous music) - [Narrator] Back in Kenwood, Jacob Franks was still reeling from the news that his son was murdered, when the phone rang again.

(ominous music) (phone ringing) The caller identified himself as George Johnson, author of the ransom note, and said Bobby was alive and safe, and directed Mr. Franks to follow a complicated series of instructions.

- They had come up with a very elaborate plan for how the ransom money was to be delivered, and it involved getting Jacob Franks onto a moving train and picking up a second note that instructed him to throw the ransom off the train when he got to a certain point.

(ominous music) - [Narrator] In the fog of shock and grief, Jacob Franks forgot where he was told to go next, leaving police with no means to track the presumed killer.

And the Franks' were left with the unimaginable reality that their dear son was so cruelly ripped from their lives.

(soft dramatic music) - (Penny) Flora Franks was utterly bereft and hysterical and needed bedrest and sedation.

Jacob Franks held it together pretty well to help the police in any way he could to track down who had done this to his son.

Bobby's brother Jack was a year younger than him, was his best friend.

He was really struck by this.

(soft dramatic music) - [Narrator] The next morning, the Chicago Daily Tribune ran the headline, "Kidnap Rich Boy; Kill Him" (dramatic music) The news sparked a media frenzy.

(dramatic music) - (Candace) You had six newspapers in the city.

Every single one was vying for readership.

They came out twice a day, morning and night, and so they discovered that Americans really loved to read about sensational murders.

They gobbled up every detail and they wanted more.

- [Narrator] The public was enthralled with the developing mystery, where so many questions remained.

Was it a mistake?

Or something even more sinister?

(dramatic music) - So why would somebody kidnap this boy and not even wait to get the ransom before killing him?

The papers just really dug into this question and it immediately became a national crime.

(dramatic music) - Several papers offered rewards for exclusive information, and thousands of tips poured in.

Hundreds of reporters fueled outrageous coverage of the story.

- (Candace) They had reporters everywhere.

And they have no journalistic standards whatsoever.

So if they can peer through a keyhole, they will.

If they can climb through an air duct to listen, they will.

They have reporters that basically just sit around the police station waiting for a hot tip.

Reporters even paid for tips from police.

- Because Bobby was found nude, Police jumped to it must have been someone who was gay, who was trying to molest him.

And they went to Bobby's teachers.

They arrested several of his teachers.

They allegedly treated the teachers very badly.

They held them for several days.

(dramatic music) - [Narrator] Investigators also looked for clues in the ransom letter.

- (Nina) They have these typed ransom notes, and they had taken them to an expert, and the expert had told them that this note was typed on an Underwood portable typewriter and that it had a few defective keys which he could identify.

(dramatic music) - [Narrator] The expert said that the T and the F keys were slightly defective, and that the letter could be matched if the typewriter were ever found, a long shot since thousands of these models had been sold.

So they turned their focus to the pair of eyeglasses found near the body.

(dramatic music) - (Paul) And at first, who knows if they'll actually lead to anything.

The design of the frame is fairly common.

It's a sort of tortoiseshell design, but they do have a very singular hinge.

And in fact, there's only one manufacturer of eyeglasses in the city of Chicago that uses this hinge, the Almer Coe company.

And one of the unsung heroes in the story is an employee who goes through something like 50,000 records to find pairs of glasses that match the frame, prescription, and that unique hinge, and he narrows it down to three people in the city of Chicago.

- (Penny) One was made for a lady and she still had her glasses.

The other was made for a gentleman who was actually in Europe at the time, and had them with him.

And the third was made for a 19-year-old named Nathan Leopold.

(soft dramatic music) - [Narrator] Nathan Leopold, known as "Babe" to his family and friends, lived with his wealthy family just three blocks away from the Franks' home.

(dramatic music) - Nathan Leopold is brilliant.

His IQ is soaring.

- (Erik) He studied a dozen languages.

He'd given talks at Harvard.

He did have a lot of friends, but he was very arrogant and people were put off by that.

(dramatic music) - [Narrator] At just 19 years of age, Leopold had recently graduated from the University of Chicago and planned to attend Harvard Law School in the Fall.

He was a most unlikely suspect.

Still, Chicago Police needed to rule him out, since his glasses were found at the crime scene.

(ominous music) - (Candace) Not only do they think he's not guilty and have nothing to do with it, they don't even take him to the police station to question him.

They take him instead to the LaSalle Hotel, so that no one at the police station will see them bringing in Nathan Leopold, because they don't want to cast any aspersions on such a well-respected Chicago family.

(birds chirping) - [Narrator] As expected, Nathan Leopold had a plausible explanation.

He was an amateur ornithologist who taught birding classes at Wolf Lake.

- His excuse for the glasses, and it's a very good excuse, is that, "I could very well have dropped my glasses out there because I go out there all the time.

I was there the week before."

- [Narrator] Leopold was famous in birding circles for finding a rare Kirtland warbler.

- He went off for two different summers in Michigan searching for the Kirtland warbler, and of course, the money for this expedition was funded by his wealthy father.

- [Narrator] Seen in this film shot by a parks employee, this delicate bird is one of the rarest songbirds in the United States.

- The second summer, he does indeed find a Kirtland warbler.

And so we have this beautiful sweet video of Nathan sweetly, lovingly feeding these beautiful birds.

It was this amazing discovery.

The next day, he goes out and he kills those warblers along with the nest, and he digs up even the tree that it's on because he wants to add it to his collection.

(ominous music) - [Narrator] According to Leopold's timeline, his glasses would've been sitting out in the elements for at least four days.

Yet they were spotless when found.

Police began to wonder, could this 19-year-old wunderkind be lying?

Could he actually have been involved in the killing of a young boy?

And if so, why?

(dramatic music) - And they begin to become suspicious.

So they send some police officers to do a search of his room.

(dramatic music) - (Nina) And they find a couple of suspicious things.

One is a gun he doesn't have a permit for, and another one is a very long letter that is addressed to Richard Loeb, his best pal.

- [Narrator] The letter peaked their interest.

It seemed to imply that there was something more than friendship between the young men.

And the detectives wanted to know more about Richard Loeb.

(soft dramatic music) Known as Dickie, Loeb was 18, and the third of four sons born to Albert and Anna Loeb.

- (Stephen) Richard Loeb was a genius.

He was charismatic, he was charming, he was handsome, he was popular.

(soft dramatic music) - [Narrator] These Loeb family photos, many discovered by Richard Loeb's great-nephew in 2021, offer a new look at Loeb's privileged upbringing.

(soft dramatic music) - (Erik) The Loeb family was very prominent.

Albert Loeb was a lawyer, and then he became the vice president of Sears Roebuck.

They loved to hold exhibitions and concerts and parties.

So from an early age, Loeb was taught to be polite in front of company.

(dramatic music) - [Narrator] The Loeb family lived in one of the largest estates in Kenwood, just across the street from the Franks family.

The Loebs and the Franks' were distantly related by marriage.

(soft dramatic music) - (Erik) He started life as a kind of a prodigy.

He loved to read and he wrote scholarly articles.

He graduated high school after only two years.

And then he made up for lost time.

He went drinking and gambling and out with women.

And he was just very wild, but also very immature, because he was 14 when he entered college, so he never really got that chance to grow up.

(dramatic music) - [Narrator] In 1920, during his second year at the University of Chicago, Loeb met his match, a 15-year-old freshman named Nathan Leopold, a person he would be linked to for the rest of his life.

- (Candace) They didn't like each other at first.

Richard looked at Nathan and said, "He's just a jerk."

Nathan looked at Richard and thought, "Oh, he's just too much of a pretty boy.

He thinks he's so handsome and so charming, and I think he's so fake."

But they keep coming across each other on campus at the University of Chicago, and eventually they recognize something within each other.

(soft dramatic music) - [Narrator] Leopold and Loeb became close friends.

And when Loeb transferred to the University of Michigan the following year, Leopold followed.

At age 17, Richard Loeb became the youngest graduate of that school.

- (Erik) Richard Loeb, from the outside, looked incredibly successful.

He was part of a fraternity.

He had girlfriends.

He had lots of friends.

He loved to play sports.

He seemed like the perfect young teenage boy.

- [Narrator] In 1923, Richard Loeb and Nathan Leopold were both graduate students back at the University of Chicago.

And by the time investigators discovered the letter Leopold wrote to Loeb, the two young men had become extremely close.

In fact, Leopold's letter insinuated that they had had a sexual relationship, and then a falling out.

- (Nina) And he's worried about word getting out there that they've had a kind of lovers' spat and that people will gossip about this as a breakup of a sexual relationship.

So he says they have to be very careful about that.

So the police are immediately suspicious of this.

- Back to how people perceived homosexuality in the early 1920s, they saw that as a problem, right?

That there was some criminality there.

And so they haul in Richard Loeb.

They don't expect Richard to have anything to do with this.

How could he possibly?

But they think that they can use this letter to sort of blackmail Richard a little bit.

"You tell us about Nathan, we won't tell anybody about this letter and this relationship that you're having."

And that's where it all begins.

So suddenly they have both teens in custody, in questioning.

(soft dramatic music) - [Narrator] State's Attorney Robert Crowe had had a hunch he was on the right track, and began turning the screws on Richard Loeb.

But Loeb gave up nothing new.

He told the same story Leopold had been telling for six hours, that they were together on the day of Bobby Franks' murder.

(soft dramatic music) - The alibi is that Leopold and Loeb went out in Leopold's car and they picked up some girls and they were drinking with the girls and they were flirting with the girls.

And so the evening ends with them letting the girls out of the car and going home.

(soft dramatic music) - They said they spent all day together in Leopold's red Willys-Knight sedan, and got home after 10:00 PM.

(soft dramatic music) - They can't really crack this alibi.

Both teens say this was what happened.

(soft dramatic music) - [Narrator] Throughout the day, Leopold and Loeb stuck to their story and the trail seemed to go cold.

That is, until two rookie Chicago Daily News reporters, James Mulroy and Alvin Goldstein, started doing some investigating of their own.

Mulroy and Goldstein were also grad students at the University of Chicago, and they had been tipped off that their classmates were the prime suspects in the Franks' murder.

They also knew that police were looking for a portable Underwood typewriter in connection with the ransom note.

- These reporters, being on campus themselves, they were able to speak with law students that had worked with Nathan Leopold.

And those students told them, "Well, yeah.

Yeah, he had a typewriter like that and he used to type up our notes on it."

One of those students still had those notes and handed them over.

(dramatic music) - [Narrator] Reporters took the notes to the same typewriter expert who had reviewed the ransom letter.

(dramatic music) - [Candace] And what they realized is it's the same typewriter with that faulty lowercase f and t. - And he says, "These match."

(dramatic music) - [Narrator] The reporters had a major scoop and a new piece of evidence that could break the case.

Back in the interrogation rooms, Leopold and Loeb had been holding fast to their alibi for 18 hours, and police were close to letting them walk.

Then, just after 6:00 PM, Mulroy and Goldstein raced over to share the shocking new evidence.

(dramatic music) - (Nina) So this ends up being one of the things that breaks the case, and they end up winning the Pulitzer Prize for their detective work.

Meanwhile, Leopold is still in police custody, still in this interrogation, and they start asking him, "Do you own an Underwood portable typewriter?"

(dramatic music) Leopold begins to remember that he might actually have had an Underwood portable typewriter, but he's very evasive about it.

(dramatic music) - [Narrator] Still, Leopold and Loeb did not stray from their alibi, until a surprise visitor changed everything.

(dramatic music) - Because the questioning of the boys looks like it's going to extend well into the night and into the next day, the families back in Kenwood decide to send the Leopold family chauffeur, Sven England, to the LaSalle Hotel, basically with a change of clothes and some food for Leopold and Loeb.

(ominous music) - [Narrator] Once there, the chauffeur overheard that the questioning was centered around Leopold's red Willys-Knight model car.

And he thought he could help clear his Master Babe, as he called Nathan Leopold.

- Sven England says, "You know what?

My master could not have driven anybody out and dumped it at Wolf Lake because I had the car in the garage."

And Crowe was confused.

He's like, "Well, you had it till dinnertime.

They came back and got it."

And England's like, "No, they never got it.

I always had it.

It was always in the garage."

And suddenly Crowe was just like he leaps up and I think the quote is, "I got 'em.

I got 'em.

We got 'em."

(dramatic music) - State's Attorney Crowe initially goes to Loeb.

He tells Richard Loeb that, "I know for a fact that you guys cannot have been in that red Willys-Knight automobile because of the testimony of Sven England."

And almost immediately Richard Loeb folds.

- Richard cracks, completely and totally cracks.

After Richard squeals, they go down to Nathan and they say, "Richard said everything."

And at first Nathan doesn't believe it.

And then Crowe pretty much says to him, "Listen, Richard said that you are the one that killed Bobby.

And he was just in on it."

And that's when Nathan says, "Let me tell you what really happened."

(dramatic music) - (Nina) Once they start to tell it, they really wanna tell it.

They almost begin to brag about their brilliant plan.

And they each describe it in incredible detail.

- [Narrator] Both Leopold and Loeb said they planned what they thought would be the perfect murder for six months.

- They loved the planning aspect, just being able to bounce ideas off each other.

"What if we did this?

What if we did that?"

"Well, what if we killed your father?"

"No, then we couldn't get the ransom."

"What if we killed your brother?"

"No, because then there would be too much attention on us."

And it was just testing every little point, getting it absolutely perfect.

They loved it.

(dramatic music) - [Narrator] Both told police that they purchased a chisel, acid, and rope to use in their crime.

They spent several weeks creating a fake identity called Morton D. Ballard, whose name they used to rent a blue sedan.

That's what they were driving the day they decided to head out and choose a random child to kidnap and murder, which they described in chilling detail.

(dramatic music) - [Leopold] The next problem was getting the victim to kill.

This was left undecided until the day.

We decided to pick the most likely-looking subject that came our way.

(dramatic music) - [Narrator] As fate would have it, it was young Bobby Franks who was walking their way.

- Richard Loeb leaned over and called him over, and he said, "Hey, I want to talk to you about that tennis racket you use.

I want to get a tennis racket like that for my brother.

Can I talk to you about it?"

- [Narrator] Not only were Richard Loeb and Bobby Franks neighbors and distant relatives, but they also regularly played tennis together at the Loeb family courts.

So Bobby trusted Loeb enough to get into the car.

(dramatic music) - [Leopold] As soon as we turned the corner, Richard placed his one hand over Robert's mouth to stifle his outcries, with his right, beat him on the head several times with a chisel.

(dramatic music) - (Paul) I can't imagine what must have been going through Bobby's mind.

Bobby struggles.

He starts to scream and to yell.

- [Loeb] Leopold then took one of the rags and gagged him by sticking it down his throat.

- The person in the backseat pulls Bobby into the backseat with him, and then takes a cloth soaked in chloroform and instantly stuffs it down into Bobby's mouth, who dies as a result of asphyxiation.

(dramatic music) - (Erik) The plan had been to strangle him to death, that they would wrap a rope around his neck, and both of them would pull on one end of the rope, so they would be equally culpable of this murder.

But he had suffocated without them realizing.

(dramatic music) - (Nina) And they drive down to near the Indiana border and it isn't dark out yet.

And so they need to kill some time before they can take the body out of the car without a risk of being seen.

And they go to this hotdog stand.

Now Bobby's dead body is in the backseat covered by a blanket and they have a snack in the front seat.

(dramatic music) - [Loeb] We dragged the body out of the car, put the body in the robe and carried it over to the culvert.

Leopold carried the feet, I carried the head.

We deposited the body near the culvert, and undressed the body completely.

- They used hydrochloric acid to try to mask the identity of Bobby, and then they put his body in the culvert.

They thought it would be relatively simple, but getting him there is a challenge.

They leave his feet exposed, sticking out of the culvert.

(dramatic music) - [Narrator] Both denied any sexual assault.

(soft dramatic music) - After they leave Bobby's body, they go to mail a ransom note.

And it had been pre-typed the night before and it was mailed to Bobby's family.

Leopold called the Franks' home and he said, "Your son has been kidnapped, and he's fine, and instructions will follow on how to get him back."

(dramatic music) - [Narrator] Once back in their own neighborhood, they inexplicably decided to toss the murder weapon from Leopold's car, where it was picked up and turned over to police by a night watchman.

Leopold and Loeb then disposed of Bobby's clothes and tried to erase any trace of evidence.

Their confessions were nearly identical, except for one key point.

(dramatic music) - (Nina) Leopold says that Loeb actually killed Bobby, and Loeb says that Leopold actually killed Bobby.

And when they're told that, that each one of them is accusing the other one, that also just makes them both furious.

- (Leigh) Of course, they both blamed one another.

But who could tell?

Again, that's another part of the mystery.

Who was lying, who wasn't lying?

Who was worse of the two?

- [Narrator] In the eyes of the law, they were both equally responsible, and after 72 hours of questioning, police finally had what they needed.

(soft dramatic music) 10 days after the murder of Bobby Franks, the confessions were plastered on the front page of newspapers around the nation, and the story of Leopold and Loeb's sinister murder plot quickly became a true crime obsession.

(dramatic music) - (Sarah) The newspapers called it the crime of the century when they saw that an 18-year-old and a 19-year-old, well-educated boys from these well-connected families, had murdered a 14-year-old boy who also lived in their neighborhood and was part of their community.

- [Candace] It becomes a national sensation.

Every aspect of this crime is looked at.

- A lot of the newspapers called on phrenologists to study their facial features and the shapes of their heads to see if there was any clues.

These studies showed that Loeb was weak, Loeb was feminine, and Leopold was strong and sex-craved and masculine.

- (Sarah) When papers can sell by telling you one more salacious detail each day, having one more drawing of Leopold's head that shows you just where you can see his criminality and sexuality, people are fascinated by it.

(soft dramatic music) - [Narrator] Leopold and Loeb seemed to relish the limelight.

(soft dramatic music) - Once Leopold and Loeb confessed to the murder, they took the police reporters on sort of a murder tour.

They took them to all of the sites where everything happened, where they killed Bobby Franks, where they hid everything.

- [Narrator] From the location of the clothes they buried to the Jackson Park Lagoon, where they disposed of the typewriter, they even reenacted how they lured Bobby into the car.

(soft dramatic music) The prosecution brought in psychologists, called alienists at the time, to thoroughly examine the suspects.

Leopold and Loeb both willingly told their examiners about every aspect of their lives, from their childhoods to their twisted pact sealed three years earlier while the teens traveled in a private train car to the Loeb family's palatial estate in Charlevoix, Michigan.

- (Candace) On that train trip, Nathan confesses to Richard about his homosexual tendencies.

And this is a big confession because it's the early 1920s, and homosexuality is illegal.

Richard then confesses to Nathan about how he wishes that he was a master criminal, and how he really has been committing crimes, stealing things, stealing money from friends, that sort of thing.

- He didn't just want to steal things, he wanted to do more.

He wanted to do more ambitious crimes.

- So now they feel like they've confessed to each other.

And so this is the first time they have a sexual relationship is on that train.

- What Loeb wanted was a partner in crime.

He wanted somebody to come out and secretly commit these wonderful crimes with him.

And what Leopold wanted, apparently, was sex.

- And I believe that that need, that each had something that the other wanted, really drove them.

(soft dramatic music) - [Candace] They start small, they steal cars.

They take a baseball bat and break windows and break into people's houses.

(soft dramatic music) - [Narrator] In fact, they even stole the portable Underwood typewriter, used to write their ransom note, from Richard Loeb's fraternity house.

(dramatic music) - And it's not long after, they commit this sort of string of burglaries that they decide that they want to go one step beyond that and see if they can actually take a human life and get away with it.

And that's what leads them to ultimately kidnap and murder Bobby Franks.

(soft dramatic music) - [Narrator] After he confessed, Nathan Leopold told police that what drove the pair to commit murder was, "...the pure love of excitement."

He also credited his interest in German philosophy.

(dramatic music) - (Candace) He believes in Nietzsche.

This idea of the superman, that there are certain people that are so superior that they're above the law, that they're above the constraints of society.

And he actually believes that he is a superman.

Nathan is attracted sexually to Richard, and he also begins to see him as a fellow superman.

(dramatic music) - [Narrator] But these so-called supermen were not above the law after all.

And Robert Crowe was out to see them hanged.

- There is no doubt in anybody's mind, especially in the State's Attorney's mind, that they will get the death penalty.

(dramatic music) - [Narrator] Meanwhile, their victim's family was left with a horrific task of burying their youngest son.

(soft dramatic music) On a spring day, perfect for a game of baseball, eight school boys carried their friend Bobby Franks' flower-draped casket out of his home to a waiting hearse.

(soft dramatic music) - (Penny) They look quite young and they're wearing their Sunday best, and they have their hair slicked down.

And they're simply, got their little hands through the handles on the side of his casket.

- [Narrator] Bobby was laid to rest in his family's mausoleum.

(soft dramatic music) - (Nina) Jacob Franks had only recently built this mausoleum at Rosehill Cemetery, I'm sure, not assuming that Bobby was gonna be the first family member who went in.

Obviously, this family was completely devastated.

(soft dramatic music) - [Narrator] The Franks' family could not mourn their son in peace.

They were swarmed by reporters, neighbors, and curious onlookers for months.

- (Nina) There was nonstop traffic past this house.

So not only was this family in tremendous grief, but they were now in this fishbowl of just public gawkers who just wanted a glimpse inside the house of this boy who had been murdered.

- [Narrator] The Leopold and Loeb families were devastated as well by their teenage sons' unthinkable crime.

But, they also wanted to save their lives.

For this, they called on Clarence Darrow.

- (Leigh) And who was Clarence Darrow?

The most famous defense attorney of his day by far.

And he was the kind of person who dominated a courtroom and he was a brilliant strategist.

- (Penny) They went over to his apartment and knocked on his door and offered him any amount of money to save their boys from the hangman, and he was also really against the death penalty.

He felt it was subhuman and savage and not fitting for modern society, so he was willing to take up the case.

(gentle music) - [Narrator] Rumors swirled that Darrow took the case for a $1 million fee, although the actual amount was around $65,000.

The families were accused of trying to buy their way out of justice.

Leopold and Loeb both pleaded not guilty.

Speculation was that they would claim insanity as a defense.

But as the trial approached, Clarence Darrow held a surprise close to his vest.

(soft dramatic music) On a 93-degree day in July, 300 people, including 200 reporters, packed into a Chicago criminal courtroom.

- (Erik) The public was hugely interested in the trial.

They waited outside the doors every day to get a chance to be inside the courtroom, just to get a glimpse at Leopold and Loeb.

(dramatic music) - [Narrator] Standing before Judge John Caverly in the sweltering heat, Clarence Darrow delivered a shocking twist.

He announced that his clients would withdraw their pleas of not guilty and plead guilty instead.

The crowd gasped.

There would be no trial.

(dramatic music) - (Leigh) Clarence Darrow never let on that he was gonna plead his defendants guilty.

He just led the prosecutor on, and he fell for it hook, line, and sinker.

So supposedly the prosecutor was so stunned when Clarence Darrow said both of them are pleading guilty that he was really flummoxed and didn't know what to do.

- His brilliance was, "If I have them plead guilty, we go right to our sentencing hearing.

And then it all depends on one judge."

He was betting on the humanity of the judge as opposed to a jury.

(dramatic music) - [Narrator] Two days later, the sentencing hearing began.

Robert Crowe called all 102 witnesses planned for trial, including Jacob and Flora Franks, who described their beloved son Bobby.

Crowe said that Leopold and Loeb were as much entitled to the mercy of the court as a couple of rattlesnakes.

Through it all, the accused killers appeared unbothered.

- (Sarah) I think most of us, if we knew that we were participating in a hearing, and the two outcomes were life in prison or the death penalty, we might not look relaxed or confident.

It was yet one more thing that fed the interest in them.

How could these people have done this?

Why do they not look contrite?

Why do they not at least look scared?

(dramatic music) - (Leigh) Clarence Darrow's strategy was, "Let's get the judge to see these young men as human beings, because then he will make a decision not to execute them."

- They weren't mobsters, they weren't bank robbers.

They weren't notorious criminals.

They weren't Al Capone.

They weren't Bonnie and Clyde.

They were just two nice Jewish boys from Chicago.

(gentle music) - [Narrator] Darrow had his work cut out for him.

The state aimed to kill and his clients' smugness wasn't helping.

- (Candace) And that's when he brings in the idea of a mitigating circumstance.

This idea that they'd had these terrible childhoods.

- [Narrator] Darrow called up the top psychiatrists of the day, not to argue insanity, but something new to the court of law.

The idea that Leopold and Loeb were not totally responsible for their actions, that their privileged upbringing, in part, made them do it.

- We see from the stories that were told to the psychiatrist, that both of these boys were really raised by nannies and governesses.

- They'd had parents that hadn't paid attention to 'em.

In Richard's case, this controlling governess, in Nathan's case, the governess that sexually abused him.

Surely this had some impact on who they became as teenagers and the crime that they ultimately committed.

(soft dramatic music) - [Narrator] Clarence Darrow began his closing argument on August 23rd, 1924.

It lasted for more than 12 hours, over two and a half days.

Darrow told the court, "For God's sake, if the state in which I live is not kinder, more human, more considerate, more intelligent than the mad act of these two mad boys, I am sorry I have lived so long."

(soft dramatic music) After 32 days, the hearing was adjourned.

- And the only question was, would they hang or would they get life in prison?

And getting life in prison was the win.

(soft dramatic music) - [Narrator] Two weeks later, Judge Caverly sentenced Nathan Leopold and Richard Loeb to life in prison for the murder of Bobby Franks, plus 99 years for his kidnapping.

(dramatic music) At 19 years old, Leopold and Loeb entered Joliet State Prison.

Six months later, Leopold was moved to Stateville.

The verdict offered little solace to the Franks' family.

Jacob Franks died four years after his young son.

He willed $100,000 towards a memorial for Bobby.

- They created a clubhouse where other children could go and play.

They wanted to celebrate his life.

(soft dramatic music) - [Narrator] On July 21st, 1930, Flora Franks and her surviving son Jack broke ground for the Robert Franks Clubhouse in Chicago.

- Bobby Franks was a 14-year-old going to school, playing baseball, doing his homework, not worrying his mother, being best friends with his brother, being a little brother to his sister, being the apple of his father's eye.

That's how Bobby Franks should be remembered.

(soft dramatic music) - [Narrator] Jack Franks said that, "Bobby's death left an aching void in our hearts."

And said the family hoped that, "Hundreds of boys will be happy here."

The clubhouse served the community for more than 50 years, fulfilling the family's wish.

(soft dramatic music) Nathan Leopold and Richard Loeb lived out their adulthood behind bars.

Loeb created a school for inmates, writing often to his mother Anna about his progress, in these letters discovered by the Loeb family in 2021.

- [Loeb] Dearest Mompsie, the geometry course is shaping up quite well.

On the whole, I never find it difficult to pass the time away.

In fact, most days I could use a few extra hours."

- (Erik) And he wrote a textbook, eventually.

He advised prisoners, "When you're writing home, don't complain because your family knows you don't want to be here, so don't bog things down.

Be happy and they'll be happy."

(soft dramatic music) - [Narrator] After six years apart, Loeb was transferred to Stateville Prison, where he reconnected with Leopold.

They spent much of their time there working on an inmate school together.

Records show that Loeb was relatively well-liked in prison and did not have enemies.

Nonetheless, in 1936, James Day, a prisoner serving 10 years for armed robbery, stabbed Loeb in the shower 56 times.

Day later claimed he was acting in self-defense and was acquitted, but the full story may never be known.

(dramatic music) - (Erik) Doctors determined that the first cut had actually been from behind to his neck.

That was not a defensive attack.

It was definitely premeditated.

It's very hard to say what the real story behind that was.

- [Narrator] When told of the attack, Nathan Leopold rushed to the infirmary.

He offered to donate blood, but it was too late.

Loeb took his last breath and Leopold covered him with a sheet.

Richard Loeb was 30 years old.

- (Erik) When Loeb died, Leopold was kept in the psychiatric cells for six months to make sure that he didn't kill himself or try to go for revenge or anything like that.

And after Loeb died, Leopold spent a lot of time with their school.

He took over running the school.

He wanted to make it a memorial for Loeb.

(soft dramatic music) - [Narrator] Leopold's later request for release was closely followed by the press and public.

- [Reporter] Do you think that you would be more useful on the outside and how?

- I definitely would hope to be more useful on the outside and how, well I would have larger opportunities to use whatever small talents I have.

- [Narrator] Leopold said that he was a changed man who had, in his youth, succumbed to Richard Loeb's influence.

- (Erik) He said, "Look, this was something Loeb wanted to do.

We are equally guilty under the law.

I'm not saying I'm not guilty, but this is something that Loeb wanted to do.

And I loved him and I admired him, and I would've done anything he said to keep his friendship."

And because Loeb had died in this way that cast so much negative publicity on him, it was easy for people to turn and say, "Oh, Loeb was the evil one then, and Leopold was the good one."

(dramatic music) - [Narrator] After several unsuccessful attempts, Leopold was finally released on parole in 1958.

After spending 33 years behind bars, he agreed to a single press conference on his release.

- In my appearance before the board, I solemnly pledged that I would avoid every form of publicity.

That pledge I will keep to the letter.

Please, make it easier for me by not asking me to break that pledge.

(indistinct chattering) - [Narrator] Leopold moved to Puerto Rico, where he wrote a memoir and a book on the birds of the island and married a Puerto Rican widow in 1961.

Ten years later, at age 66, Leopold died of a heart attack.

(dramatic music) - (Erik) The thing that most impresses me about Leopold's character is that he was a hedonist.

His happiness was the only thing that mattered.

It mattered more than someone else's life or someone else's discomfort.

He said that about himself in the '20s.

He said it about himself in prison.

He said it about himself the year he died.

That was how he operated.

(dramatic music) - [Narrator] Whichever of the two killers one chooses to find more culpable, the case continues to inspire endless interest.

- (Stephen) They had all of the privilege.

They had the money to be defended by the great Clarence Darrow.

Were they not from the station in life that they were, they would've hung.

But it's because of who they were and where they came from that caused us to still be talking about them, writing books, movies, plays, songs to this day.

(soft dramatic music) - (Nina) I don't think that public fascination with it will die, because it does have many of the elements of a myth about good and evil, and those are questions we can't answer.

We can only tell the story and ask the questions.

- I think the biggest question is this: Were Nathan and Richard just sort of aberrant monsters, or is their behavior somehow a reflection of our American culture?

And I think that's what still resonates with us a hundred years later.

(soft dramatic music) (dramatic music)