16 is way too young to be handling those kind of money right. Without proper guidance, these kind of wins burn in flames together with the winner.
I think that you can never get too comfortable or too cocky. Power and money can and will influence the brain. But from highs you can drop very low. I admire when people keep their cool at 5 $ as much as at 50000$.

Give a person a little more power/money and it will only accentuate the flaws in their financial behavior.