You know, it's funny--now that you mention it, I never believed Dean gambled it away out of selfishness, though that's what John believes in my story. I've read, and written, so many fics in which the boys just didn't have enough money and supplemented in some way, usually with gambling, that I assumed that's what happened and that John just doesn't know it, whether because they never told him or because he doesn't want to believe he doesn't provide properly for his boys. But I could also see your scenario of overconfidence and cockiness, especially if he was a very young teenager ... :-)

So glad you liked it!