Adobe is notorious difficult to run on Linux, even with wine. It’s one of the few things that I’d dare say could lock someone to windows unfortunately

They probably removed certain libraries that are used by 32 bit programs

Unless his attitude and stance changes, there’s not a single red team that I could see taking him. You can’t just throw someone who wants to be a criminal into pentesting and think it’ll go well

He’s talented, but the problem is jobs like pen testing require a LOT of trust to work in. So far this guy has said and shown that he intents on staying in cybercrime rather than doing legitimate work.

As it stands, given how he’s acted, I can’t see a single company that would let him pen test their systems or a red team that would take that risk to their reputation.