We have two girls - 29 and 19. Our oldest was a bit rebellious and drank with her rich friends from 13 - 15 years old. But at that age, she thought a beer can was surgically attached to my hand, so I set her free to drink. Our youngest is showing her defiance now by dying her hair different colors and a "Monroe piercing". That's been it. They are both pretty and had guys hitting on them relentlessly. They never gave in to that temptation. My oldest daughter thanks me regularly that I did did not back down. I had a rule - 10:30!!! The only thing to do after 10:30 is get in trouble. Every time someone locally got in trouble, I asked them "What time did this happen?" It was always after 10:30. There were special occasions where the rule was bent, but not often. Kids today respect no one but themselves. They learn this from Nickelodeon and other kids programs that show these smart independant children with idiots for parents (do the simpsons come to mind? I ain't talkin bout OJ!).
I am not going to give parenting advice because I've seen so many "good kids gone bad" due to peer pressure. All I can say is when they are growing up, you have to make them feel that they are important to you (or make them feel good about themselves), make them learn to fear consequences (beat their as$es). But the most important part that lets them see that civilization and respect for others is clear cut, is the part I am not allowed to discuss here. PM me and we can talk.
So, as far as Brad goes - turn his life off. Keep doing what you're doing. You will have to deal with his depression shortly, because he will become depressed.
My best wishes and prayers are with you and Brad.