Chicago's Thrill Killers

Published July 27, 2021
Chicago's Thrill Killers


On this date, May 21, 1924, the sons of two of Chicago's wealthiest and most illustrious families drove to the Harvard School on the city's South Side and kidnapped a young boy named Bobby Franks. Their plan was to carry out the "perfect murder." It was a scheme so devious that only two men of superior intellect, such as their own, could accomplish. These two were Richard Loeb and Nathan Leopold. They were the privileged heirs of well-known Chicago families who had embarked on a life of crime for fun and for the pure thrill of it. They were also a pair of sexual deviants who considered themselves to be "brilliant" --- a claim that would later lead to their downfall.

Bobby Franks

Nathan Leopold, or "Babe" as his friends knew him, had been born in 1906 and from an early age had a number of sexual encounters, starting with the advances of a governess and culminating in a relationship with Richard Loeb. He was an excellent student with a genius IQ and was only 18 when he graduated from the University of Chicago. He was an expert ornithologist and botanist and spoke nine languages fluently. Like many future killers, his family life was totally empty and devoid of control. His mother had died when he was young and his father gave him little personal attention. He compensated for his lack of fatherly direction with expensive presents and huge sums of money. Leopold was given $3,000 to tour Europe before entering Harvard Law School, a car of his own and a $125-a-week allowance.

Richard Loeb was the son of the Vice President of Sears & Roebuck and while he was as wealthy as his friend was, Loeb was merely a clever young man and far from brilliant. He was, however, quite handsome and charming and what he lacked in intelligence, he more than made up for in arrogance. Both of the young men were obsessed with perfection. To them, perfection meant being above all others, which their station in life endorsed. They felt they were immune to laws and criticism, which meant they were perfect.

     Chicago’s infamous “Thrill Killers”, Richard Loeb and Nathan Leopold standing on either side of their famous defense attorney, Clarence Darrow. 

Loeb fancied himself a master criminal detective, but his dream was to commit the perfect crime. With his more docile companion in tow, Loeb began developing what he believed to be the perfect scheme. He also constantly searched for ways to control others. Leopold, who was easily dominated, agreed to join him in a life of crime. Over the course of the next four years, they committed robbery, vandalism, arson and petty theft, but this was not enough for Loeb. He dreamed of something bigger. A murder, he convinced his friend, would be their greatest intellectual challenge.

They worked out a plan during the next seven months. The plan was to kidnap someone and they would make it appear as though that person was being held for ransom. They would write the ransom note on a typewriter that had been stolen from Loeb's old fraternity house at the University of Michigan and make the family of the victim believe that he would be returned to them. Leopold and Loeb had no such plans though ---- they intended to kill their captive.

In May 1924, they rented a car and drove to a hardware store at 43rd and Cottage Avenue, where they purchased some rope, a chisel and a bottle of hydrochloric acid. They would garrote their victim, stab him with the chisel if necessary, and then destroy his identity with the acid.

The next day, they met at Leopold's home and wrapped the handle of the chisel with adhesive tape so that it offered a better grip. They also gathered together a blanket and strips of cloth that could be used to wrap up and bind their victim. Leopold also placed a pair of wading boots in the car because the boys planned to deposit the body in the swamps near Wolf Lake, located south of the city. They packed loaded pistols for each of them and looked over the already typed ransom note that demanded $10,000 in cash. Neither of them needed the money but they felt the note would convince the authorities that the kidnappers were lowly, money-hungry criminals and deflect attention from people like Leopold and Loeb.

They had only overlooked one thing ---- a victim.

They first considered killing Loeb's younger brother, Tommy, but they discarded that idea. It was not because Tommy was a family member but only because it would have been hard for Loeb to collect the ransom money without arousing suspicion. They also considering killing Armand Deutsch, grandson of millionaire philanthropist Julius Rosenwald, but also dismissed this idea because Rosenwald was the president of Sears & Roebuck and Loeb's father's immediate boss. They also came close to agreeing to kill their friend, Richard Rubel, who regularly had lunch with them. Rubel was ruled out, not because he was a good friend to them, but because they knew his father was cheap and would never agree to pay the ransom.

They could not agree on anyone but did feel that their victim should be small, so that he could be easily subdued. With that in mind, they decided to check out the Harvard Preparatory School, which was located across the street from Leopold's home. They climbed into their rental car and began to drive. As they drove, Leopold noticed some boys near Ellis Avenue and Loeb pointed out one of them that he recognized --- 14-year-old Bobby Franks. He was the son of the millionaire Jacob Franks, and a distant cousin of Loeb.

Chosen by chance, he would make the perfect victim for the perfect crime.

Bobby was already acquainted with his killers. He had played tennis with Loeb several times and he happily climbed into the car. Although at their trial, both denied being the actual killer, Leopold was at the wheel and Loeb was in the back, gripping the murder weapon tightly in his hands. They drove Bobby to within a few blocks of the Franks residence in Hyde Park and then Loeb suddenly grabbed the boy, stuffed a gag in his mouth and smashed his skull four times with a chisel. The rope had been forgotten. Bobby collapsed onto the floor of the car, unconscious and bleeding badly.

When Leopold saw the blood spurting from Bobby's head, he cried out, "Oh God, I didn't know it would be like this!"

Loeb ignored him, intent on his horrific task. Even though Bobby was unconscious, he stuffed his mouth with rags and wrapped him up in the heavy blanket. The boy continued to bleed for a time and then died.

With the excitement of the actual murder concluded, Leopold and Loeb casually drove south, stopped for lunch, and then drove for a little while longer. They had supper as they waited for the sun to go down. Eventually, they ended up near a culvert along the Pennsylvania Railroad tracks. It emptied into a swamp along Wolf Lake.

Leopold put on his hip boots and carried Bobby's body to the culvert. They had stripped all of the clothes from the boy's body and then after dunking his head underwater to make sure that he was dead, they poured acid on his face in hopes that he would be harder to identify. Leopold then struggled to shove the naked boy into the pipe and took his coat off to make the work easier. Unknown to the killers, a pair of eyeglasses were in the pocket of Leopold's coat and they fell out into the water when he removed it. This would be the undoing of the "perfect crime."

After pushing the body as far into the pipe as he could, Leopold sloshed out of the mud toward the car, where Loeb waited for him. The killers believed that the body would not be found until long after the ransom money had been received. With darkness falling, though, Leopold failed to notice that Bobby's foot was dangling from the end of the culvert.

They drove back to the city and parked the rental car next to a large apartment building. Bobby's blood had soaked through the blanket that he had been wrapped in and had stained the automobile's upholstery. The blanket was hidden in a nearby yard and the boys burned Bobby's clothing at Leopold's house. They typed out the Franks' address on the already prepared ransom note. After this, they hurried back to the car and drove to Indiana, where they buried the shoes that Bobby had worn and everything that he had on him that was made from metal, including his belt buckle and class pin from the prep school.

Finally, their "perfect crime" carried out, they drove back to Leopold's home and spent the rest of the evening drinking and playing cards. Around midnight, they telephoned the Franks' home and told Mr. Franks that he could soon expect a ransom demand for the return of his son. "Tell the police and he will be killed at once," they told Mr. Franks. "You will receive a ransom note with instructions tomorrow."

The next morning, the ransom note, signed with the name "George Johnson," was delivered to the Franks, demanding $10,000 in old, unmarked $10 and $20 bills. The money was to be placed in a cigar box that should be wrapped in white paper and sealed with wax.  After its arrival, the Franks' lawyer notified the police, who promised no publicity.

Meanwhile, Leopold and Loeb continued with the elaborate game they had concocted. They took the bloody blanket to an empty lot, burned it, and then drove to Jackson Park, where Loeb tore the keys out of his stolen typewriter. He threw the keys into one lagoon in the park and the typewriter into another. Later in the afternoon, Loeb took a train ride to Michigan City, leaving a note addressed to the Franks in the telegram slot of a desk in the train's observation car. He got off the train at 63rd Street, as it returned to the city, and rejoined the waiting Leopold. Andy Russo, a yardman, found the letter and sent it to the Franks.

However, by the time the letter arrived, railroad maintenance men had already stumbled upon the body of Bobby Franks. The police notified Jacob Franks and he sent his brother-in-law to identify the body. He confirmed that it was Bobby and the newspapers went into overdrive, producing "extra" editions that were on the street in a matter of hours.

One of the largest manhunts in the history of Chicago began. Witnesses and suspects were picked up in huge numbers and slowly the "perfect crime" began to unravel. Despite their "mental prowess" and "high intelligence," Leopold and Loeb were quickly caught. Leopold had dropped his eyeglasses near the spot where the body had been hidden and police had traced the prescription to Albert Coe & Co., who stated that only three pair of glasses with such unusual frames had been sold. One pair belonged to an attorney, who was away in Europe, the other to a woman and the third pair had been sold to Nathan Leopold.

Police officers search for clues at Wolf Lake, where Bobby Franks’ body was found
The boys were brought in for questioning and began supplying alibis for the time when Bobby had gone missing. They had been with two girlfriends, they claimed, "May and Edna." The police asked them to produce the girls but the killers could not. Leopold claimed that he had apparently lost the glasses at Wolf Lake during a recent bird-hunting trip. The detectives noted that it had rained a few days before but the glasses were clean. Could Leopold explain this? He couldn't.
Then, two novice reporters, Al Goldstein and Jim Mulroy, obtained letters that Richard Loeb had written with the stolen typewriter --- which had already been found in Jackson Park. The letters matched the type on the ransom note, which was a perfect match for the typewriter that Leopold had "borrowed" from his fraternity house the year before.
Loeb broke first. He said that the murder was a lark, an experiment in crime to see if the "perfect murder" could be carried out. He then denied being the killer and claimed that he had driven the car while Leopold had slashed Bobby Franks to death. Leopold refuted this. Finally, the boys were brought together and admitted the truth. Loeb had been the killer, Leopold had driven the car but both of them had planned the crime together --- they were both guilty of Bobby Franks' murder.

The people of Chicago, and the rest of the nation, were stunned. It was fully expected that the two would receive a death sentence for the callous and cold-blooded crime.

After the confession, Loeb's family disowned him but Leopold's father turned to Clarence Darrow, America's most famous defense attorney, in hopes that he might save his son. For $100,000, Darrow agreed to seek the best possible verdict that he could, which in this case was life in prison. "While the State is trying Loeb and Leopold," Darrow said. "I will try capital punishment."

Darrow would have less trouble with the case than he would with his clients, who constantly clowned around and hammed it up in the courtroom. The newspaper photographers frequently snapped photos of them smirking and laughing in court and the public, already turned against them, became even more hostile toward the "poor little rich boys."

Darrow was fighting an uphill battle, but he brought out every trick in the book and used shameless tactics during the trial. He declared the boys to be insane. Leopold, he said, was a dangerous schizophrenic. They weren't criminals, he railed, they just couldn't help themselves. After this weighty proclamation, Darrow actually began to weep. The trial became a landmark in criminal law. He offered a detailed description of what would happen to the boys as they were hanged, providing a graphic image of bodily functions and physical pain. Darrow even turned to the prosecutor and invited him to personally perform the execution.

Darrow's horrifying description had a marked effect on the courtroom and especially on the defendants. Loeb was observed to shudder and Leopold got so hysterical that he had to be taken out of the courtroom. Darrow then wept for the defendants, wept for Bobby Franks, and then wept for defendants and victims everywhere. He managed to get the best verdict possible out of the case. The defendants were given life in prison for Bobby Frank's murder and an additional 99 years for his kidnapping.

Ironically, after all of that, Darrow only managed to get $40,000 of his fee from Leopold's father. He got this after a seven-month wait and the threat of a lawsuit.

Leopold and Loeb were sent to the Joliet Penitentiary. Even though the warden claimed they were treated just like all of the other prisoners, they each enjoyed a private cell, books, a desk, a filing cabinet and even pet birds. They also showered away from the other prisoners and took their meals, which were prepared to order, in the officers' lounge. Leopold was allowed to keep a flower garden. They were also permitted any number of unsupervised visitors. The doors to their cells were usually left open and they had passes to visit one another at any time.

Richard Loeb was eventually killed by another inmate, against whom he had been reportedly making sexual advances. The inmate, James Day, turned on him in a bathroom and attached him with a razor. Loeb, covered in blood, managed to make it out of the bathroom and he collapsed in the hallway. He was found bleeding by guards and he died a short time later. It was later discovered that Day had slashed him 56 times with the razor. When Clarence Darrow was told of Loeb's death, he slowly shook his head. "He is better off dead," the great attorney said, "For him, death is an easier sentence."

Leopold lived on in prison for many years and was said to have made many adjustments to his character and some would even say rehabilitated completely. Even so, appeals for his parole were turned down three times. Finally, in 1958, the poet Carl Sandburg, who even went as far as to offer Leopold a room in his own home, pleaded his fourth appeal. Finally, in March of that year, he was released.

He was allowed to go to Puerto Rico, where he worked among the poor and married a widow named Trudi Feldman Garcia de Quevedo, who owned a flower shop. He went on to write a book about his experiences called Life Plus 99 Years and continued to be hounded by the press for his role in the "perfect murder" that he had committed decades before. He stated that he would be "haunted" by what he had done for the rest of his life.

Nathan Leopold died of heart failure on August 30, 1971, bringing an end to one of the most harrowing stories in the history of the city.

Sending Leopold and Loeb to prison, according to many people, did not bring about an end to this macabre case, thanks to two restless ghosts that continued to walk for many years afterward. The spirit with the most horrible connection to the case was that of Bobby Franks, who took nearly 50 years to find peace.

During this time, visitors to Rosehill Cemetery on the north side of Chicago often reported seeing the ghost of a young boy standing among the stones and mausoleums in the Jewish section of the graveyard. It is here where the Franks family mausoleum is located, although its location is not listed on any maps of the cemetery and employees are instructed not to point it out to curiosity-seekers. Even so, this tomb can be discovered within the confines of the beautiful burial ground and starting in the 1920s, maintenance workers and visitors alike encountered the ghostly boy. Many came to believe that it was the ghost of Bobby Franks, unable to rest in the wake of his bloody and violent death.

Franks Mausoleum

The boy was often seen wandering here but only from a distance. Whenever he was approached, the apparition would vanish. These sightings continued for years but eventually, they seemed to fade away. It's been noted that the encounters ended at nearly the exact same time that Nathan Leopold died in Puerto Rico. Could there be a connection between these two events? It certainly seems possible and perhaps Bobby Frank can now find peace on the other side.

The other ghost from this case was that of famous attorney Clarence Darrow. When Darrow died in 1936, his ashes were scattered over the lagoon at Jackson Park, just behind the Museum of Science and Industry. While standing on what has been named the Clarence Darrow Bridge, many people have somewhat regularly spotted what is likely Darrow's ghost on a veranda that spans the back of the museum. This wide stone area is at the bottom of the steps leading into the rear entrance of the museum. The ghost is reportedly seen dressed in a suit, hat and overcoat and bears a striking resemblance to the attorney. The figure is reported to stand and stare out across the water before disappearing.

Does the ghost of Clarence Darrow walk at the Museum of Science and Industry?

Is this the ghost of Clarence Darrow, finally making his presence known from a world beyond our own? There are no other ghostly manifestations connected to this site and certainly none that look like Darrow did in his last days, as he strolled through the park admiring the "prettiest view on Earth."

The story of Leopold and Loeb – along with dozens of other sensational Chicago crimes, ghost stories and strange happenings – can be found in the book WEIRD CHICAGO, from the creators of the famous tour. The book is available in print and in a Kindle edition!


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