By Richard Jerome
June 14, 1999 12:00 PM

To his ghastly misfortune, 14-year-old Bobby Franks umpired a baseball game at Chicago’s exclusive Harvard School for Boys on May 21, 1924. Afterward, he was walking home when he accepted a ride from his distant cousin Richard Loeb, 18, and Nathan Leopold Jr., 19, both University of Chicago postgraduate students who, like Franks, came from wealthy Jewish families on the South Side. What happened next, most historians maintain, was that Loeb struck Bobby four times on the head with a chisel. When the boy “did not succumb as readily as we had believed,” Leopold later said, Loeb shoved a cloth into his mouth, suffocating him. After nightfall they took the corpse to a park where Leopold, an avid ornithologist, often went birding. They poured disfiguring acid over the child’s face, then forced his body down a drain.

A gruesome landmark in the annals of American crime, the murder became the first of several notorious cases to be designated Crime of the Century. Even now, on the slaying’s 75th anniversary, Leopold and Loeb remain symbols of senseless killing. “It captured the nightmare imagination of the country—because it was so cold-blooded, because it was children killing children,” says author Geoffrey Cowan, comparing it to the recent slaughter at Columbine High School. “It seemed so hard to believe.”

The case also secured Clarence Darrow’s place as one of the most skilled attorneys of his or any other era. After persuading the boys to plead guilty, he focused his efforts on saving them from execution. His impassioned plea brought tears to the eyes of the judge and spurred a national debate on the morality of the death penalty. “You may hang these boys,” Darrow told Judge John Caverly. “But in doing it you are making it harder for every other boy who in ignorance and darkness must grope his way through the mazes which only childhood knows.” The killers got life plus 99 years.

Given their economic and intellectual background, Leopold and Loeb seemed unlikely murderers. Leopold had a 200 IQ and spoke five foreign languages. Loeb was reportedly the youngest-ever graduate of the University of Michigan. Evidently, the pair saw the crime as an intellectual exercise, though a misplaced infatuation clearly played a role as well. Scion of a shipping family, “Babe” Leopold was a University of Michigan freshman when he became smitten with roommate “Dickie” Loeb, the brash, handsome son of a Sears, Roebuck vice president. Enamored of Nietzsche’s theory that some men are inherently superior, Leopold idolized Loeb (“I felt myself less than the dust beneath his feet,” he later said). If not actually gay, Dickie did see an opportunity to form a partnership in a quest that had obsessed him since boyhood: committing the perfect crime. As a court psychiatrist put it, “Leopold acquiesced in Loeb’s criminalistic endeavors” and received “biological satisfactions” in return. “I had not then learned to control the fierce emotions of adolescence,” Leopold later wrote. “I did what he wanted.”

In the fall of 1923 the two began plotting. They would kidnap and kill a rich child, then collect a $10,000 ransom. On May 21, 1924, Leopold used a false name to rent a blue Willys-Knight touring car, much like his own red one. Then he and Loeb drove to the Harvard School in search of a boy from their list of potential victims. One of them, Armand Deutsch, then 11, is alive today because he had a dentist appointment that afternoon. “I would have jumped in a car with them in a minute,” says Deutsch, 86, a writer. Leopold and Loeb stalked another target but lost track of him. Then Bobby Franks came by.

After the boy was killed, Leopold called Bobby’s parents to say their son had been kidnapped, then mailed a ransom note. But when the next day’s papers revealed that Bobby’s body had been found, he and Loeb abandoned their scheme. Feeling safe, Leopold was stunned on May 29 when he was called in for questioning. At the spot where the body was discovered, a pair of eyeglasses had been found. Only one local firm sold that brand, and just three people had bought it. One was out of the country, and a second still had her pair. The third was Leopold. Babe said the glasses must have fallen from his pocket while he was bird-watching that day. Reciting the alibi he and Loeb had devised, he added that after birding they had picked up two girls and gone cruising in Leopold’s red Willys. But evidence mounted against them. A family chauffeur had worked on Leopold’s car all day on May 21. Then two reporters compared the type on the ransom note to Leopold’s term papers and found that certain letters matched. Loeb confessed, followed by Leopold—though each said the other had swung the chisel.

In prison at Joliet and later Stateville, Ill., the two remained close and started an education program for inmates. On Jan. 28, 1936, they shared a breakfast of sweet rolls, then corrected papers. But that noon Dickie was killed, slashed more than 50 times in the shower by a razor-wielding inmate who claimed Loeb had made a sexual advance. Leopold was at the prison hospital to say goodbye. “He had been my best pal,” he wrote. “In one sense he was also the greatest enemy I have ever had.”

In later years, Leopold made a concerted effort to prove he had been rehabilitated. He taught, worked as an X-ray technician and volunteered for a World War II malaria experiment. He also wrote an autobiography, Life Plus 99 Years. In time, polls favored Leopold’s release, and allies such as poet Carl Sandburg lobbied on his behalf. He was paroled at last in March 1958. Leaving prison with lawyer Elmer Gertz, Babe vomited. “He hadn’t been in a car in 34 years,” says Gertz, 92. “He got nauseous.”

Two days later, Leopold landed in Puerto Rico, where he had been offered work, and a new life, as a lab technician at the Church of the Brethren hospital. “I told him he was two days old when he came to Puerto Rico,” says retired Judge Angel Umpierre, 94, then head of the island’s parole board. Given an apartment and a $10 monthly stipend (he lived off a modest inheritance), Leopold performed a range of community work. “He was a tremendous individual with the talent of opening people’s hearts,” says John Forbes, 72, a hospital colleague. “He was good with children,” adds Elsa Groff, 75, then head nurse. Indeed, the celebrated child-killer was known as Mr. Lollipop for the treats he gave young patients. Leopold earned a master’s in social work at the University of Puerto Rico and also wrote a book on the island’s birds. Still, he chafed under parole restrictions—he had a curfew and couldn’t drink or drive. Says Gertz: “He just hated authority.”

In February 1961, at 56, Leopold married Gertrude “Trudi” Feldman Garcia de Quevedo, an American-born widow he had met at a Passover seder. “They were pretty affectionate,” says a friend. “But he didn’t lose his sexual orientation.” Freed from parole in 1963, Leopold traveled the world. On Aug. 30, 1971, wracked by diabetes and heart disease, he died at 66 in a hospital near San Juan. Late in life, Leopold had assiduously avoided discussing his crime. But for many years the photos of two men were displayed in his apartment. One was Clarence Darrow. The other was Richard Loeb.

Richard Jerome

Lorna Grisby in Chicago, Don Sider in Puerto Rico and Champ Clark in Los Angeles