The skill set developed for breaking in is different than the skill set for building security. Winkler might want to look at how NSA does their security checking. I hear they have two completely separated teams. One team secures, the other breaks in.

Winkler makes a judgment call on Mitnick. As the employer, he has the right to do so. I think he is ignoring Mitnick paid for his indiscretions and his youthful hackers did not. So how are they more "repentant"?

In my estimate the best test of a safe's security is to hire a safe cracker, not ask the designer of the safe.

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