5. Am I My Brother's Keeper?

Charles Tiffany was so brilliant at marketing luxury to the newly minted millionaires of the gilded age that he left $12 million to his four children when he died in 1902.  Not trusting his younger son Burnett to manage his money wisely, he created a $1.5 million trust for him overseen by his older son Louis.  Indeed, Burney went bankrupt less than two years later... but only because Louis refused to pay off a $25,000  debt for furniture Burney had bought for his new wife.