Crowe was born in 1879 in Peoria, Illinois. After graduating from the Yale Law School in 1901, Crowe returned to Illinois to practice. From 1916 to 1921, Crowe was a judge of the Circuit Court of Cook County. In 1921, he moved to the position he occupied at the time of the Franks murder.
By all accounts, Crowe conducted his investigation of the Franks murder in a thorough and professional manner. No doubt also, he enjoyed the hunt. When Leopold's chauffeur provided a key piece of evidence in the mounting case against the two boys, Crowe's response was "God damn, I think we've got them!" At the conclusion of Leopold's confession, Crowe asked Nathan, "Have you been treated decently by me?" Leopold replied, "Absolutely."
Anticipating a possible insanity defense, Crowe immediately proceeded to retain the four best known alienists (forensic psychiatrists) in Chicago, forcing Darrow to look elsewhere to find what Crowe at trial called his "wise men from the East." Crowe presented his case with the same thoroughness as he did his investigation. He offered 102 witnesses, even though both defendants had confessed and plead guilty. Crowe's summation was a mixture of sarcasm for the defense case, careful recitation of evidence, and warnings about the consequences of accepting the "doctrines of anarchy." Although Darrow's summation is far more famous, Crowe's speech also received praise and is included in Frederick Hick's collection of "Famous American Jury Speeches." Crowe's summation contains far fewer personal reflections than does Darrow's, but it does suggest that Crowe thought himself to be a humane, decent, open-minded family man. He bristled at the defense's complaint that his decision to seek the death penalty was heartless: "I have never been cruel or vicious to any living person in my life." He proclaimed his love for his four children, his wife, and even his "good friend Clarence Darrow," with whom he had once traveled on a Chautauqau trip, talking about crime and punishment issues.
Crowe lived to reconsider his belief that death was the appropriate punishment for Nathan Leopold. In the 1950's, he offered to write a letter supporting Leopold's release from prison on the condition that the letter would not be made public until after his death. No letter was ever found.