I suspect when doing it to irritate someone, the same would apply as in option 4 where you would only do it to someone you know couldn't kill you.

Just run through this scenario, imagine the boss that picked Foghorns pockets wanted to irritate him because he simply didn't like Foghorn. They knew Foghorn was very unlikely to shoot, they also knew that if Foghorn did shoot, the odds would be steeped heavily against him hitting - and either way, Foghorn's shot would most likely be his death if he hit or missed. So the boss managed to piss off Foghorn by pickpocketing him to the extent that Foghorn felt justified in this speech, which ultimately let to his death. Most of the time, they'll just pickpocket them, the victim will get annoyed and do nothing about it. What ever happens though, if there is anything to learn from this case other than think before you speak, Pick Pocketing to irritate someone clearly works!

Godmother ScipitaRourke in my opinion has great city rules with regards to pick pocketing.

Well well Foghorn_Leghorn... you've certainly set your leaders in a unconfortable position. For 5k... is this really worth it. As Wise Guy, you must know that you are being watched by your leaders. They were probably going to make you one of their's. The best thing to do in this situation is take the pill and bank your cash in the futur. Sometimes the pill is hard to take, i must agree my ancestors previously swallowed some difficult pills. But they eventualy became honorable men. It is not a good idea to have a godfather on your bad side in this time of your life. For what it's worth, only thing i can say is... good luck kid! Being on your own is the last thing that should come to mind in this thing of ours.