I’m a firm believer in meritocracy and the importance of rewarding skills. He should still pay a hefty price for his crimes, including jail time, where he will hopefully learn to change his ways, but once he gets out, if he’s truly remorseful for his actions and he’s willing to have others monitor his device usage activities, I don’t see why he shouldn’t be hired by a red team

The thing is, people who are highly skilled at computers and pentesting aren't that rare. Working in the industry also requires trustworthiness, reliability, communication skills, the ability to work well with others, and many other things - those are all key "merits", too.

It doesn't matter how good he is at typing rapidly and then saying "I'm in!" if he's too unreliable and untrustworthy to actually get work done, or if his communication skills suck to the point where he can't / won't convey the problems he finds and how to fix them.