[quote name='mykevermin']Depending on how persistent he's been with his 'hobbies' over the years, your denial would only be putting off the inevitable, IMO.
I'm sorry it went down like that and I'm sure you feel like shit. If, however, (1) you don't think you'll really help him (that this would be the end of this lifestyle) and (2) you feel that your help is only in vain because he's lying about the extent and nature of the problem, ultimately, family or not, how can you feel responsible for the plights of someone who is most likely that deceitful to you?
I'm surprised it's been two weeks without him being hurt. The problem with organized crime is that you can't go to the police, any assistance (say, if you spot him $1,000) could ultimately make you a culpable colleague of his (both form the police and mob's vantage points), and they are assuredly persistent in getting their due.
I hope the situation goes well; I can't imagine it will, since I assume he flipped/panicked on you when you told him no. Being out of options and indebted to the mafia is the worst place to be. His last remaining hope is that he's not worth enough to harm that much.[/quote]
I do not feel responsible at all for what happens to him. It is not my fault he owes money to the mob or whoever and cannot pay it back. It's not my fault at all if someone shows up and breaks his legs today. What bothers me is that I'll feel guilty if it happens and giving him the money could have prevented it.
The fact still remains that I cannot get involved - period. I just can't and the second I hand him a penny I would become involved (even though he was swearing up and down that I wouldn't be). First, I have a family to think about and they are my top priority. I can't take even the smallest chance that my name would get out and someone would come to me to collect the rest of his debt. Second, I have a career to think about to support my family and an ethics committee to answer to should this ever get out somehow (believe it or not

). Involvement in something like this could mean the end of my career - unlikely but why risk it?
He did flip out on me when I kept telling him no. It was one of the worst conversations I've ever had - he was crying and begging and I could tell he was angry and scared. I'm not 100% sure he is being completely honest with me either (although give him an Oscar if he's lying). Is this the last payment owed? Is it really for gambling? If he does have a gambling problem is this money really going towards his debt? The sad thing is that he *only* needs $2,500 - I can't imagine not being able to put that together. He said he got the rest of the money he owes from friends. He kept repeating that "$2,500 and these guys are out of my life forever."
I feel like shit and I think our relationship is probably permanently altered from this point on and it's unfortunate. I have a close knit family and he is really the only black sheep - it's going to make things awkward. He just didn't understand how I could say no to family for something this serious. At the same time he still refused to tell his parents and I'm debating whether or not to tell them myself (well, at least tell my other uncle knowing full well it would probably get back to my cousin's dad). I think I'm leaning towards saying something - I want to help, I don't want to see him get hurt but I cannot give him the money and get involved like that under any circumstance.
Any thoughts?