4. Harold and Elaine Messner
Lottery Winnings: $166,5 million
They have done the best thing a lottery winner can do, and with doing so, they had to be included on our list of 5 most successful lottery winners and their good stories. After winning half of Mega Millions $390 million jackpot in 2007, the couple hired a lawyer to represent them. They opted for an early retirement and didn’t give any interviews later, wanting to enjoy their money in quiet.