Talk about a voluntary tax on stupidity, where winning means loosing. Have at it guys. If one of you wins I promise not to hit you up for cash.
The big problem is that having a metric crapton of money will not change how you *relate* to money. All more money does is magnify your tendencies.
If you are a spendthrift, you will be an EPIC waster of money.
If you are a miser, your need for control and paranoia over your money will be equally EPIC.
If you are pretty smart and balanced with money, AND make a concerted effort to remain so, you can do well.
The problem in that case is not that your relationship with money gets warped, it's that all your interpersonal relationships get warped by money because everybody else's money dysfunctions come out on display too.
Several years ago I heard a radio interview with a guy who won $100 mil, and was doing very well with it. He said the hardest lesson for him to learn, and one that was very difficult for him, was that he needed to make all new friends.
His old friends saw him as a regular guy with this big windfall that they wanted to be part of, and felt somewhat entitled to since they "knew him when he was nobody."
When he detached from those old friends and made new ones, the new friends just always knew him as a "really rich guy" and they more or less left him alone. Plus, a lot of the new friends were rich themselves so that helped also.