if you're a 'normal/intelligent' guy in prison, you stand out nicely against the complete fucking morons who've grown up huffing gas, smoking weed, and cooking meth 2/3's their lives.
not hard to 'sway' a prison staffer... women prison guards arn't the easiest, but if they believe you' can get them an extra $1k/month by bringing in tobacco, they're in... once they're in, you can exthort them into giving up some pussy because if they get caught bringing in tobacco, they're gonna go to prison as well.
prison nurses, doctors, dental workers, teachers, ect... are MUCH easier.