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.
Probably the hardest part
I mean, what is it you can't do when you can, not only coerce people into knowingly committing a federal crime for you, potentially carrying decades long prison sentences... But also can coerce them into taking the fall, for you, if they ever get caught....
Because that's "cartel" type of "can do" things right there... It requires a hell of large sticks...
Espionage training teaches you to look for the just-slightly-problematic. The people that find themselves in a bad situation are often the most vulnerable. It's not always the obvious that gets you in trouble.
You'd think that stick has to be big, but I guarantee you that people that are going through a rough spot can be manipulated the easiest. It's one of the reasons things like alcoholism and a bad credit score can keep you out of a job in certain industries.
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