Is that good or bad?

So, the iPod was in his desk. Friend has the Nintendo. I drove to the school undecided over whether I hoped to find it in his desk or not find it. Finding it meant he did, in fact, take it. The gray part is whether he took it because he was asked to or because he actually stole it. But, in today's world - it doesn't matter. He is the one caught with illegal stuff that isn't his in his desk. So, crack - two counts. His teacher is being very cool, but the thought is there in all our minds. I tried to think of real life examples and explain to him why it's a stupid choice. During said explanation he simply said "I did it because I didn't think I'd get caught".
HE ALWAYS GETS CAUGHT. How long does it take to figure that one out? I have a team of eyes and ears and really, they are telling me mostly the bigger stuff - who knows how much little stuff happens? Egads...this trip home for the holidays will be ok. I will make it ok...but it won't be fun and I wanted to just sit back and have fun. If I had a threat level colored warning - I'd be on red right now!