I'm not sure why you need that trait in software. You're (usually) not trying to beat other programmers. So I suppose the parent comment should have added "except in adversarial situations".
Which means it does apply to cyber security. You need hackers to outsmart hackers. If that's the kind of industry you're applying for, it probably is a good idea to mention this actually.
That's different. According to that page, Abagnale served 5 years in prison (6 months in solitary confinement), and had to work for the feds for a while "without pay". Then when he first got legitimate work, he was usually fired.
I'd be willing to hire someone who cheated and was caught and served time, but not someone who cheated without consequence and boasted about it.
The commenter here doesn't sound like they segued that into a career catching academic cheaters. They just used it as a stepping stone to their next personal accomplishment.
After serving his time, that's exactly how Frank Abagnale got a job in the FBI.
https://en.wikipedia.org/wiki/Frank_Abagnale