Complex sentence: While the media expected Leopold and Loeb to plead not guilty by reason of insanity, Darrow advised his clients to plead guilty, avoiding a trial by jury, which Darrow believed would most certainly have resulted in a conviction and perhaps even the death penalty.
Split into simpler sentences: While the media expected Leopold and Loeb to plead not guilty by reason of insanity, Darrow surprised everyone by having them both plead guilty. In this way, Darrow avoided a jury trial, which he believed would most certainly have resulted in a conviction and perhaps even the death penalty.