The Leopold and Loeb case is interesting for two philosophical reasons. The first is that Clarence Darrow, their lawyer, used determinism as an argument in their defence. It was evidently effective as the defendants avoided the death penalty for kidnapping and murder.
The second reason is that Leopold and Loeb were influenced by Nietzsche and as highly intellectual 'super men' they thought they could commit the perfect crime. There is a good account of the case here.
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