Teaching my kids about bullies and douchebag rich kids

It's coming to that point with my oldest son, Gavin, is having to learn to deal with little douchebag kids that have unclever, snarky, rich-kid, bullsh*t to say to him.  I don't necessarily classify it as bullying because the kid in question hasn't laid a hand on my him but its mostly verbal assualts.  This bothers me on two different levels:  1.)  I consider myself clever and quick witted and would love for him to utilize that gene inside of his little head.  I wish he could come up with some killer put downs to this kid that would just destroy his self confidence and make him question if his birth was a mistake.  2.)  I wish I could just tell them to punch the kid and tell him to shut the f**k up.  I know that neither of these options are very good parenting on my part but its the advice that I want to give.  I have attempted to train him in the art of insults, but I quickly figured out that my insults towards people would probably warrant immediate suspension for Gavin if he used any of them.  If I am angry enough at a person, I tend to find their weakest, most personal area and destroy it.  I have said some horrible things to people in the past, some that I am not proud of and others that still bring a little grin to my face.  So without giving any examples, I told Gavin the same.  I asked him to find any sensitive areas in the kids life that he could point out and ridicule.  It sounds bad but I know the level that he is working with and he won't say anything too horrible.  His insults now consist of "jerk" and "stupid".  I don't know what his nemesis is saying but I am sure that it is not much better than that. 

I am sure that some people will say, "Oh, you should teach him to ignore it or to turn the other cheek"  People who say that were never picked on once in their life.  "Oh if you are nice to them it will drive them nuts."  Ok that works in only one of two situations which is either in the movies or when you are a little older and not in elementary school, and Gavin is 10 and this isn't any John Hughes movie.  Since I don't see the insult department getting any better for awhile with him and I don't want him to get suspended for knocking the kid's teeth out, I have suggested some things that I did when I got pissed off at someone back in school as well as some things not to do.

As for the not to do's:  The first time I ever remember actually really getting picked on, besides some petty crap in elementary school, was in 7th grade.  It was an awkward year and I remember that I was taller than everyone else except my friend Gammon.  I had these three little shits, Charlie Stirsman, Derrick Wills, and Travis Statzer all making fun of me constantly for about a week.  I don't even remember what it was about, I just remember that they wouldn't shut up and  I couldn't come up with a whole lot to say back.  Finally after lunch on the 5th day, our class was lined up in the hall waiting to go back to class and Statzer, who came up to my belly button at the time, kept jumping around and taunting me.  I told him over and over to shut his tiny mouth up but it just kept going.  In a moment of anger, I turned around in his direction and threw a punch where I thought he was and put my fist through the wall right between his head and Mikey Good.  Silence fell over everyone and was only broken up when my teacher, Mrs. Cain, yelled "Mr. Elliott, what do you think you are doing?"  Stupid 7th grade me said, "Uhh, I put a hole in the wall?!?"  I didn't get time to explain and was marched to the principal's office.  I tried to explain to Ms. Morelock what had been going on and she explained that violence was never the answer and I was ordered to pay $10 to patch up the hole.  I used this story to Gavin and he just thought it was cool that I punched a hole in the wall and kept asking how big it was.  I'm not sure that he got the message that it was the wrong thing, and stupid.

I had no more real problems with anyone throughout middle school, just minor things.  It was then that I realized that I had a perfect outlet to take care of anyone's mouth or problem that was being given to me.  I played football since I was 7 years old and although I was pretty good, a lot of the time I was passive.  I did enough to get the job I was supposed to be doing done.  I blocked my guy or I made the tackle and that was it.  During that same time that I put the hole in the wall, we just so happened to be in football season and all the guys that had been giving me a hard time happened to be fellow teammates.  So that next week I made it a point to punish them everytime I had a chance.  If one of them was running the ball, I pretended that I was Lawrence Taylor and they were a fragile ballet dancer holding a bag of cocaine.  I would hit them with the full force of anger, frustration, and hatred in my body.  It started to feel good to me and from then on out that was how I solved my problems.  I put it out on the football field.
Gavin and Kyler both recently started playing football and I relayed this bit of knowledge to them because Gavin's tormentor just so happens to be on their team.  I explained to him to be cool at school and just nod his head when this little snot ran his mouth and tell him to wait until 4 o'clock to rolls around.

Football, I believe, also helped me in my clever/mean department.  Kids all the way from little league to college talk trash during the game and you have to be able to shoot back something to them even if you are a better player.  A couple of instances during high school, I had been arguing with a guy we all called "Booger" and he was not the best player by any stretch of the imagination.  I would pound him into the ground everytime and he would pop up and say something like, "Is that all you got, you overgrown pussy?"  It perplexed me to no end.  I would line up against him and do it again.  Same result.  It was like watching Rocky getting killed by Ivan Drago in Rocky IV.  Eventually after about a week of this, we shook hands and settled our differences but I learned that I had to really step up my game in the insult department.  So during games in high school, I would make it a point to know something personal about a few players on the other team and make sure to loudly and rudely point it out.  I got pretty good (or bad depending on how you look at it) with it.  I would find the kid who I heard about his father leaving his mother and yell out, "Why doesn't your dad love you anymore?" or tell him "I'm the reason you don't have a father, I'm banging your mom."  I'm not necessarily proud of these things (maybe a little) but it helped me be a better, more fierce player.  I wouldn't do this to anyone on my team but I would still try to seek out and punish anyone that I felt had wronged me.   Oddly enough, with these situations I can remember the actions taken but I can't remember what any of the fights were about.  I told my son this part as well, that these things were so insignifigant in the grand scheme of life that I couldn't even remember what we were fighting about in the first place.
Needless to say, none of this was much comfort to him yet and it won't be until he actually implements these actions.  He went to school today and I reminded him of what we talked about before he left.  However, I am still waiting for a call from school telling me that he has finally gotten into a full scale brawl in lunch or something.   
I'm sure that it will take time for him to learn how to deal with bullies and douchebag rich kids.  We all have our ways of dealing with it and maybe he will find his own.  I will say though that I am holding out on the chance that he has some of my "smartass" in him.