John R. Caverly was the Chief Justice of the Circuit Court of Cook County at the time of the Leopold-Loeb trial. Caverly was no hanging judge, and both Darrow and Crowe knew it. Darrow wrote later that he believed Caverly to be "kindly and discerning in his views of life." Darrow was also aware of Caverly's solicitude for youthful offenders and his work in establishing a juvenile court system in Chicago.

Robert Crowe understood that Darrow's decision to plead the defendants guilty was an effort to have the sentencing decision made by a "friendly judge." His suggestion of this motivation for the plea in open court, however, drew an angry response from Caverly, who called it "a cowardly and dastardly assault upon the integrity of this court," and ordered the remark stricken from the record.

Caverly rested his decision not to execute Leopold and Loeb almost entirely on the defendants' youth, prompting Leopold to wonder whether they might have gotten the same result if they had simply submitted their birth certificates into evidence.