I should've expected it sooner; he is my kid, after all.
So it turns out that my son has been scamming breakfasts at school. We had been mystified at the charge bills, the "free lunch" applications and calls from the school saying he was on "alternative meals" until we paid up. He eats at home, and has a lunch packed every day. However, these charges kept piling up. Finally, my wife gets in contact with the head lunch lady for an explanation.
The boy has been eating a second breakfast at school everyday, in addition to his home breakfast (No word on "elevensies", though). In addition, he's supposed to be on "alternative" meals, since he maxed out his account limit -- alternative breakfast is milk and a pack of graham crackers. Despite this, he's been getting milk, juice, and cereal every day. How you ask? Pure cute mixed with pitifulness, that's how. He just doesn't have the money (which is true, since we don't give him any). This has been sorted out rather quickly, now that we know what's going on, but the kid's a good manipulator.
Now, why should I have expected this, just because he's my spawn? Because I did almost exactly the same thing. My school lunches at that age cost $0.50, with a quarter for milk. After the main meal, you could buy ice cream for an extra quarter. With this setup, my parents provided me with a dollar a day. Being the greedy little sonofabitch I was, I decided that a daily quarter was more valuable than a daily ice cream (this thought process led me to accumulate over $100 over a couple of years, which was not insubstantial given my age and the decade involved). Over time, my teachers noticed that while I looked longingly at the ice cream, I never purchased any. Given that I lived in a little craphole of a trailerpark within sight of the school, they assumed I just didn't have the money, and started slipping me ice cream. They never actually asked me if I had the money or not, and my little 5-year-old mind went "SCORE"! The situation lasted until the first parent-teacher conference, and I didn't get in trouble, since I hadn't really lied to anyone to acquire the ice cream. Still, that experience was pretty typical, and my son seems to be following in my footsteps.
Now we just have to wait until he manages to get engaged with a team sport, and see if he gets involved in a gambling scandal, like I did with soccer in 3rd grade.