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Carence Darrow came out of retirement several times. Once for the Scopes trial, once for the Leopold and Leob trial and once for the Massie case in Honolulu.

The Massie affair began in 1931 when a young navy wife Thalia Massie claimed she had been gang raped by four or five Hawaiians. Arrests followed and a jury, which included two Chinese and two Japanese jurors, heard final arguments on December 1, 1931. After ninety seven hours of deliberations the jury announced they were deadlocked at six to six. Racial tensions were high after the hung jury. Fights occurred between whites and nonwhites. Her husband, Tommie Massie was afraid a second trial might not produce a conviction so he began to plot ways to obtain a confession. He and three others kidnaped one of the defendants, Joe Kahahawai, at gun point with the plan to extract a confession out of him. However, the police were notified, but the defendant ended up dead before the police caught up with the group. Racial tensions were now very tense as the killing was seen by the local nonwhites as a lynching. The white community was in sympathy with Masssie and his friends.

A grand jury indicted the four and seventy five year old Clarence Darrow came out of retirement to assume the defense. He was promised a fee of $30,000, a very substantial amount in those days. He and his defense attorney assistant, George Leisure arrived by ship on March 24^th 1932. They were met by crowds of people and by reporters and others at the Honolulu dock. This was a celebrated case in Hawaii.

The trial began on April 4^th in a packed courtroom. After the prosecution rested, Thomas H. Massie was Darrow’s first witness. His defense was temporary insanity. Darrow called two psychiatrists to testify that the defendant had been temporarily insane at the time of the killing. He also called Thalia Massie to testify in detail about the alleged rape.

Darrow’s final argument was carried live on the radio and the courtroom was filled. Darrow argued that the mental suffering had driven the defendants to do what they did. He occasionally wiped away tears while emphasizing the "black gates of prison" that awaited them if convicted. He argued all morning and into the afternoon. It’s reported that in his conclusion he praised Hawaii as a "kindly and dispositioned people" and ended with the plea: "I ask you to be kind, understanding, considerate – both to the living and the dead."

The jury began deliberations on April 27^th and after forty seven hours their verdict was the same for each defendant: "Guilty of manslaughter. Leniency recommended." Governor Lawrence Judd received a call from the President of the United States Herbert Hoover urging that they be spared jail time. The governor agreed. He commuted their sentence "to one hour, to be served in the custody of the sheriff." The island culture was forever changed after the trial.

Clarence Darrow returned Chicago where he died on March 13, 1938 just one month shy of what would have been his 81st birthday.