[Basic] Reputations for bad people

[Railstar]

Originally Posted by David Johnston2

That is not actually a good reason not to be afraid of them or to be less afraid than you be of the famous philanthropist.

It's a good reason for the Intimidation check to fail, due to the penalty a negative reputation causes. Being scary is not always the same thing as scaring them into doing what you want - that fear can lead to other reactions, such as desperately attempting to kill you at all costs (because you have them convinced that any scenario in which you survive will lead to you coming after them).