"Hello, I'm a stranger in a bar wearing a mask and a pair of gloves, my name is michael jordan, take those 1000 bucks and insert that highly suspicious USB key at your workplace for me. Thank you. (and btw I'm not a fed and not a jew. In case you would ask.)"
You would really have to find the dumbest grunt of them all to accept such deal.... Probably too dumb to actually work for companyX, btw...
And then he takes the money, and walks away... And that's it, no more nothing, it's gone it's all gone. And he told the cops on top of that, because they are his friends...
Not necessarily wearing a mask, but operative sees Gary pull up in a car decorated with military stickers and strikes up a conversation. Operative finds out Gary works for BigDefenseCo...buys Gary a few drinks and finds out Gary is deep in debt from his wife's gambling problem. Operative offers Gary a couple grand to just stick a flash drive in a computer that operative knows is probably in a room somewhere, and Gary, almost at the point where he's going to lose his house, takes the offer...it's just a USB key, what could happen?
One of the easiest marks in the stoolie world is someone who has a problem like money. They can be desperate and will do almost anything for a hit of cash. You would think that person is extremely stupid, but they're not - they're just at the end of their rope and are susceptible to things that most people would just go "Beat it bud."
What I do know is that, if you want to manipulate an individual or group of people to do things against their will, the winning formula is the good old carrot and stick
If he/they accept the offer, they get the carrot and not the stick
If they don't, they get the stick, not the carrot. If this doesn't work it's either because the stick or the carrot aren't big enough.
...
That being said, Gary comes featured with a "self inflicted" stick in your scenario, which is already a thing required to have... It's not rare, but not granted.
Also, still in your hypothetical scenario, what guarantee do you have that Gary isn't going to accept the offer and run straight to the feds right after your drinks... After all, if he can secure a win win on this one...
Gary's featured stick hanging over his head isn't large enough to prevent just that from happening.
There's no guarantees. It's just an avenue that has to be guarded against.
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