Nathan and Richard were quickly caught. Nathan had dropped his glasses close to the spot where Bobby's body was and the police were able to trace the prescription back to him. The police were also able to trace the ransom note to a typewriter that Nathan had "borrowed" from his fraternity house the year before. When the men were being questioned by police, Richard was the one to confess first. Although Richards confession came shortly after.
The people living in Chicago and the rest of the nation were very upset and expected that there would be a death penalty for the two men. The families of the killers hired Clarence Darrow, the most famous defense attorney in America, for $100,000. Darrow promised to try to seek the best possible verdict which would be life in prison. Newspaper photographers snapped photos of the killers in the courtroom that mostly showed them smirking and laughing. This turned the public even more against them.
Darrow had to fight a tough battle and he used every trick he could. He declared both the boys to be insane. Darrow explained how Nathan was a dangerous schizophrenic. He argued that the boys were not criminals and that they could not control what they had done. During the trial, Darrow actually began to cry which caused this trial to be a landmark in criminal law. Next, Darrow described in detail what would happen to Nathan and Richard as they were hanged, being sure to give graphics. This horrifying description had an effect on the courtroom, especially the defendants. Richard shuttered a little and Nathan got so upset that he had to leave the courtroom. Darrow continued to weep.
Darrow won the case. This trial is later known as "the trial of the century." The men were given life in prison for the murder along with an additional 99 years for Bobby's kidnapping. The men's families only payed $40,000 of Darrow's fee and that was only after he had threatened to sue them.
Richard and Nathan were then sent to the state prison. A lot of the public was upset about the special treatment that the men recieved. It was obvious that money was involved because they each enjoyed a private cell, books, a desk, a filing cabinet, and even pet birds. The men were able to shower away from the other prisoners and ate their meals in the officer's lounge. Any number of unsupervised visitors were allowed to come as well and the men were allowed to keep their own gardens.
In January of 1936 Richard Loeb was murdered by another prisoner. The prisoner claimed that Richard had tried to make homosexual advances towards him so that is why he killed him. The man slashed Richard 56 times in the back with a homemade knife and he bleed to death in the shower room. The killer's claim about Richard spread rumors about him being a prison rapist. This was later found not true. The man had actually killed Richard because Richard had not given him as many cigarettes as he had given to the other prisoners.
As for Nathan, he lived in prison for many years which seemed to change his character a lot. It took four appeals for his parole until he was released in March of 1958. He later wrote a book called LIFE PLUS 99 YEARS about his experiences and then moved to Puerto Rico. While there he worked among the poor, married a widow, and died in 1971 from a heart attack.