My 10 year old son is friends with a varied group of boys. 2 I consider "trouble" because they swear and think they are the "cool kids" and are more advanced than I'd like my son to be as far as what they watch on tv, the swearing, being into girls, things like that. Then he has a group of what the other boys call the "nerdy kids"-the smart ones, computer geeky type. I saw in some text messges on my son's phone that the 2 "cool boys" were making fun of and threatening to "make you cry" to one of the geeky type kids unless the child paid them $5. I asked my son about it and he says it never actually happens (as far as physical stuff or money being paid) but they do pick on this boy alot. I have seen my son stick up for the boy and tell the boys to stop so I do not believe my son is participating. My son is bigger then all of them so he doesn't get picked on and he pretty much fits in and hangs with all different groups. So far I have not seen him gravitate to a certain group or be "clicky". My question is, do I tell the Father of the boy who is doing the threatening (he and I are neighbor's and I have ratted this boy out before for other things) or do I tell the Mom of the boy being picked on and let her handle it with her child? The boy doing the picking on basically has no adult supervision because his Father is a single Dad of 3 boys (the 10 yr old and two teenagers) and works all the time. So this boy romas the neighborhood freely all hours of the day and night, uses his phone when and however he wants, stays up all night on video games, etc. My child has limits as to where he can go alone, his phone and game usage etc. I just feel like without proper supervision, this boy will become an even bigger bully if it is not stopped now. (and he is just a little peanut himself so I am SHOCKED that kids are even threatened by him!) Advice please?